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Dimethyl methylphosphonate

PubChem CID
12958
Structure
Dimethyl methylphosphonate_small.png
Dimethyl methylphosphonate_3D_Structure.png
Molecular Formula
Synonyms
  • DIMETHYL METHYLPHOSPHONATE
  • 756-79-6
  • DMMP
  • Pyrol dmmp
  • Fyrol DMMP
Molecular Weight
124.08 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
Description
Dimethyl methylphosphonate is a clear colorless liquid with a pleasant odor. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Dimethyl methylphosphonate.png

1.2 3D Conformer

1.3 Crystal Structures

COD records with this CID as component

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[methoxy(methyl)phosphoryl]oxymethane
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C3H9O3P/c1-5-7(3,4)6-2/h1-3H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

VONWDASPFIQPDY-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

COP(=O)(C)OC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C3H9O3P
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

756-79-6

2.3.2 Deprecated CAS

351011-43-3, 880251-70-7
351011-43-3

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 UN Number

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 Nikkaji Number

2.3.9 NSC Number

2.3.10 Wikidata

2.3.11 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • dimethyl methanephosphonate
  • dimethyl methylphosphonate
  • dimethylmethylphosphonate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
124.08 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-0.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
124.02893114 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
124.02893114 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
35.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
7
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
82.2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Dimethyl methylphosphonate is a clear colorless liquid with a pleasant odor. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Liquid
Colorless liquid; [Merck Index] Pleasant odor; [CAMEO]

3.2.2 Color / Form

Colorless liquid
Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 11th ed. New York, NY: McGraw-Hill, 2006., p. 573

3.2.3 Boiling Point

358 °F at 760 mmHg (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
181 °C; 79.5 °C at 20 mm Hg
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-202

3.2.4 Melting Point

<50 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 573

3.2.5 Flash Point

110 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

3.2.6 Solubility

greater than or equal to 100 mg/mL at 70 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Miscible in alcohol, ether, benzene, acetone, carbon tetrachloride; insoluble in heavy mineral oil
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 573
Soluble in ethanol, ether
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-202
Miscible in water
Bennett GM et al; J Chem Soc pp. 1930-7 (1928)

3.2.7 Density

1.1596 at 77 °F (NTP, 1992) - Denser than water; will sink
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
1.1507 g/cu m at 20 °C
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V4: 4149

3.2.8 Vapor Pressure

1.2 mmHg at 77 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
1.2 [mmHg]
0.962 mm Hg at 25 °C
Boublik, T., Fried, V., and Hala, E., The Vapour Pressures of Pure Substances. Second Revised Edition. Amsterdam: Elsevier, 1984.

3.2.9 LogP

log Kow = -0.61
Krikorian SE et al; Quant Struct Activ 6: 65-70 (1987)

3.2.10 Refractive Index

Index of refraction: 1.4099 at 30 °C/D
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-202

3.2.11 Dissociation Constants

pKa = 2.37 in water at 20 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 573

3.2.12 Kovats Retention Index

Standard non-polar
839 , 839 , 840 , 915
Semi-standard non-polar
881 , 868 , 876 , 881 , 860.6 , 880.9
Standard polar
1493 , 1493.6 , 1501

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Classes -> Organophosphates, Other

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
D169102
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 3
View All
13C NMR Spectra
13C NMR: 42 (Johnson and Jankowski, Varbon-13 NMR Spectra, John Wiley & Sons, New York)
2 of 3
View All
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.1.3 31P NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
Thumbnail
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2 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 7
View All
NIST Number
233393
Library
Main library
Total Peaks
40
m/z Top Peak
94
m/z 2nd Highest
79
m/z 3rd Highest
109
Thumbnail
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2 of 7
View All
NIST Number
273151
Library
Replicate library
Total Peaks
42
m/z Top Peak
79
m/z 2nd Highest
94
m/z 3rd Highest
47
Thumbnail
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4.2.2 MS-MS

NIST Number
1020799
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
125.0362
Total Peaks
3
m/z Top Peak
111
m/z 2nd Highest
125
m/z 3rd Highest
93
Thumbnail
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4.2.3 Other MS

Other MS
MASS: 70265 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)

4.3 UV Spectra

MAX ABSORPTION (ALCOHOL): 217 NM (LOG E= 1.12)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 57th ed. Cleveland: CRC Press Inc., 1976., p. C-376
UV: HBCP
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V4: 4149

4.4 IR Spectra

IR Spectra
IR: 10468 (DMS)

4.4.1 FTIR Spectra

1 of 2
Instrument Name
PERKIN-ELMER 1710
Technique
NEAT
Source of Sample
Akzo Chemicals Inc.
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
Bio-Rad FTS
Technique
Neat (KBr)
Source of Spectrum
Forensic Spectral Research
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.2 ATR-IR Spectra

1 of 2
Instrument Name
PerkinElmer SpectrumTwo
Technique
ATR-IR
Copyright
Copyright © 2013-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Aldrich
Catalog Number
D169102
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.3 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
D169102
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

Catalog Number
D169102
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Central Nervous System Stimulants
A loosely defined group of drugs that tend to increase behavioral alertness, agitation, or excitation. They work by a variety of mechanisms, but usually not by direct excitation of neurons. The many drugs that have such actions as side effects to their main therapeutic use are not included here. (See all compounds classified as Central Nervous System Stimulants.)

7.2 Absorption, Distribution and Excretion

Dimethyl methylphosphonate (DMMP) is a widely used chemical. Diethyl ethylphosphonate (DEEP) has been proposed as a replacement for DMMP in several applications. ... To further characterize the toxicology of DMMP and DEEP, ... the biotransformation of these compounds and their ability to induce alpha(2u)-globulin accumulation in kidney /were investigated/. Biotransformation of both DMMP and DEEP were studied in male and female rats after single oral doses of 50 and 100 mg/kg. 31P-NMR and GC/MS showed that unchanged DMMP was excreted with urine; methyl phosphonate was identified as the only metabolite in urine. Unchanged DEEP was also excreted with urine; in addition, ethyl ethylphosphonate and ethylphosphonate were urinary metabolites. The majority of the applied dose of both compounds was recovered in urine within 24 hr indicating rapid absorption and excretion. No sex-differences in rates of formation or excretion of metabolites were seen.
Blumbach K et al; Toxicol Sci 53 (1): 24-32 (2000)

7.3 Metabolism / Metabolites

Dimethyl methylphosphonate (DMMP) is a widely used chemical. Diethyl ethylphosphonate (DEEP) has been proposed as a replacement for DMMP in several applications. ... To further characterize the toxicology of DMMP and DEEP, ... the biotransformation of these compounds and their ability to induce alpha(2u)-globulin accumulation in kidney /were investigated/. Biotransformation of both DMMP and DEEP were studied in male and female rats after single oral doses of 50 and 100 mg/kg. 31P-NMR and GC/MS showed that unchanged DMMP was excreted with urine; methyl phosphonate was identified as the only metabolite in urine. Unchanged DEEP was also excreted with urine; in addition, ethyl ethylphosphonate and ethylphosphonate were urinary metabolites. The majority of the applied dose of both compounds was recovered in urine within 24 hr indicating rapid absorption and excretion. No sex-differences in rates of formation or excretion of metabolites were seen.
Blumbach K et al; Toxicol Sci 53 (1): 24-32 (2000)

8 Use and Manufacturing

8.1 Uses

Sources/Uses
Used in NMR probe for cell volume, as a flame retardant, and to simulate nerve agents such as sarin; [Merck Index] Used in heavy metal extraction and solvent separation; Also used as a pre-ignition additive for gasoline, an antifoam agent, a plasticizer and stabilizer, a textile conditioner and antistatic agent, and an additive in solvents and hydraulic fluids; [HSDB]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
Industrial Processes with risk of exposure
IN HEAVY METAL EXTRACTION & SOLVENT SEPARATION; PRE-IGNITION ADDITIVE FOR GASOLINE; ANTIFOAM AGENT; PLASTICIZER & STABILIZER; TEXTILE CONDITIONER & ANTISTATIC AGENT; ADDITIVE IN SOLVENTS & LOW TEMP HYDRAULIC FLUIDS
SRI
... Simulate/s/ the physical and spectroscopic (but not the biologic) properties of anticholinesterase (nerve) agents. Dimethyl methylphosphonate is also used as a flame retardant, a preignition additive for gasoline, an antifoam agent, a plasticizer and stabilizer, a textile conditioner and antistatic agent, and an additive for solvents and low-temperature hydraulic fluids.
Toxicology & Carcinogenesis Studies of Dimethyl Methylphosphonate in F344/N Rats and B6C3F1 Mice (Gavage Studies). Technical Report Series No. 323 (1987) NIH Publication No. 88-2579 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709
Used as a flame retardant, solvent, hydraulic fluid, antifoam agent, plasticizer and stabilizer, textile conditioner and antistatic agent, a preignition additive for gasoline, and an additive for solvents and low-temperature hydraulic fluids. ... also used in the military to simulate nerve gas during testing of protective euqipment. ... listed as a chemical weapons precursor and is regulated by the Chemical Waepons Convention.
National Toxicology Program, Center for the Evaluation of Risk to Human Reproduction. NTP-CERHR Report on the Reproductive and Developmental Toxicity of Dimethyl Methylphosphonate Draft (September 22, 2004) pg 2. Available from, as of April 8, 2009: https://ntp.niehs.nih.gov/ntp/Meetings/2004/3CERHR_short_review.pdf

8.1.1 Industry Uses

  • Flame retardants
  • Intermediate
  • Flame retardant
  • Other (specify)

8.2 Methods of Manufacturing

REACTION OF TRIMETHYL PHOSPHITE OR THE SODIUM SALT OF DIMETHYL HYDROGEN PHOSPHITE AND METHYL CHLORIDE
SRI

8.3 Formulations / Preparations

Fyrol DMMP
USEPA; High Production Volume Information System (HPVIS). Detailed Chemical Results Chemical Name: Phosphonic acid, methyl-, dimethyl ester (756-79-6). Available from, as of October 16, 2008: https://www.epa.gov/chemrtk/hpvis/index.html

8.4 U.S. Production

Aggregated Product Volume

2019: 500,000 - <1,000,000 lb

2018: 100,000 - <500,000 lb

2017: 500,000 - <1,000,000 lb

2016: 500,000 - <1,000,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS
SRI
(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS
SRI
Dimethyl methylphosphonate is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program. Available from the Database Query page at: https://www.epa.gov/hpv/pubs/general/opptsrch.htm on Dimethyl Methylphosphonate (756-79-6) as of October 7, 2008
Production volumes for non-confidential chemicals reported under the Inventory Update Rule.
Year
1986
Production Range (pounds)
10 thousand - 500 thousand
Year
1990
Production Range (pounds)
>1 million - 10 million
Year
1994
Production Range (pounds)
>500 thousand - 1 million
Year
1998
Production Range (pounds)
>1 million - 10 million
Year
2002
Production Range (pounds)
>1 million - 10 million
US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Dimethyl Methylphosphonate (756-79-6). Available from, as of October 7, 2008: https://www.epa.gov/oppt/iur/tools/data/2002-vol.html

8.5 U.S. Imports

(1972) No data
SRI
(1975) No Data
SRI

8.6 U.S. Exports

(1972) No Data
SRI
(1975) No Data
SRI

8.7 General Manufacturing Information

Industry Processing Sectors
  • Plastics Product Manufacturing
  • Plastics Material and Resin Manufacturing
  • Miscellaneous Manufacturing
  • All Other Basic Inorganic Chemical Manufacturing
EPA TSCA Commercial Activity Status
Phosphonic acid, P-methyl-, dimethyl ester: ACTIVE

9 Identification

9.1 Analytic Laboratory Methods

Single-particle aerosol mass spectrometry (SPAMS) was used for the real-time detection of liquid nerve agent simulants. A total of 1000 dual-polarity time-of-flight mass spectra was obtained for micrometer-sized single particles each of dimethyl methyl phosphonate, diethyl ethyl phosphonate, diethyl phosphoramidate, and diethyl phthalate using laser fluences between 0.58 and 7.83 nJ/sq um, and mass spectral variation with laser fluence was studied. The mass spectra obtained allowed identification of single particles of the chemical warfare agent (CWA) simulants at each laser fluence used although lower laser fluences allowed more facile identification. SPAMS is presented as a promising real-time detection system for the presence of CWAs.
Martin AN et al; Anal Chem 79 (16): 6368-75 (2007)
... Detection of chemical warfare agents (CWAs) with high sensitivity and low false-alarm rates is considered an important priority for ensuring public safety. ...A minimum detection level for a CWA simulant, dimethyl methyl phosphonate (DMMP), of <0.5 ppb (parts in 10+9) /was found/ by use of a widely tunable external grating cavity quantum cascade laser and photoacoustic spectroscopy. With interferents present in Santa Monica, California street air, ... a false-alarm rate of 1:10+6 at a detection threshold of 1.6 ppb /was determined/.
Mukherjee A et al; Appl Opt 47 (10): 1543-8 (2008)

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 4
View All
Pictogram(s)
Flammable
Corrosive
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H226 (16.3%): Flammable liquid and vapor [Warning Flammable liquids]

H318 (37.1%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H319 (61.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H332 (17.1%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H340 (81.2%): May cause genetic defects [Danger Germ cell mutagenicity]

H361 (26.5%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

H361f (37.1%): Suspected of damaging fertility [Warning Reproductive toxicity]

Precautionary Statement Codes

P203, P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P317, P318, P337+P317, P370+P378, P403+P235, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 245 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Flam. Liq. 3 (16.3%)

Eye Dam. 1 (37.1%)

Eye Irrit. 2 (61.6%)

Acute Tox. 4 (17.1%)

Muta. 1B (81.2%)

Repr. 2 (26.5%)

Repr. 2 (37.1%)

Carcinogenicity - category 2

Germ cell mutagenicity - category 1B

Reproductive toxicity - category 1B

Eye irritation - category 2A

10.1.3 Health Hazards

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. Combustion products may cause breathing difficulty and pulmonary edema. It has weak cholinesterase inhibiting properties.

ACUTE/CHRONIC HAZARDS: This chemical may be harmful by inhalation, ingestion or skin absorption. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide, phosphorus oxides and phosphine. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.1.4 Fire Hazards

This chemical is combustible. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.1.5 Hazards Summary

None to very minor skin and minor eye irritant in rabbits; No reproductive or developmental toxicity observed in rats except at doses that are maternally toxic; No evidence of teratogenicity; [HSDB] Highly flammable; A skin, eye, mucous membrane, and upper respiratory tract irritant; A weak cholinesterase inhibitor; [CAMEO] Mutagenic, reproductive, and tumorigenic effects; [RTECS] Affects fertility in male rats (decreased sperm count and motility); Recovery noted after 14 weeks, but not complete by histology; No data on effects in human pregnancy; [REPROTOX]
REPROTOX - Scialli AR, Lione A, Boyle Padgett GK. Reproductive Effects of Chemical, Physical, and Biological Agents. Baltimore: The Johns Hopkins University Press, 1995.

10.2 First Aid Measures

10.2.1 First Aid

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital.

OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.3 Fire Fighting

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.4 Accidental Release Measures

10.4.1 Isolation and Evacuation

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area for at least 50 meters (150 feet) in all directions.

LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet).

FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

10.4.2 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

10.5 Handling and Storage

10.5.1 Nonfire Spill Response

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

STORAGE PRECAUTIONS: You should store this chemical under ambient temperatures, and protect it from moisture. If possible, it would be prudent to store this compound under inert atmosphere. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.6 Exposure Control and Personal Protection

10.6.1 Other Standards Regulations and Guidelines

DOE Protective Action Criteria (PAC): Temporary Emergency Exposure Limits (TEELs) for Dimethyl methylphosphonate: TEEL-0: 100 mg/cu m; PAC-1: 350 mg/cu m; PAC-2: 500 mg/cu m; PAC-3: 500 mg/cu m (TEEL-0: The threshold concentration below which most people will experience no adverse health effects; PAC-1: The maximum concentration in air below which it is believed nearly all individuals could be exposed for up to one hour without experiencing other than mild transient adverse health effects or perceiving a clearly defined objectionable odor; PAC-2: The maximum concentration in air below which it is believed nearly all individuals could be exposed for up to one hour without experiencing or developing irreversible or other serious health effects or symptoms that could impair their abilities to take protective action; PAC-3: The maximum concentration in air below which it is believed nearly all individuals could be exposed for up to one hour without experiencing or developing life-threatening health effects).
DOE (2008) Protective Action Criteria (PAC) for Chemicals - Including AEGLs, ERPGs, & TEELs (https://orise.orau.gov/emi/scapa/teels.htm); PAC Database Revision 24

10.6.2 Personal Protective Equipment (PPE)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.7 Stability and Reactivity

10.7.1 Air and Water Reactions

Highly flammable. Water soluble. Hydrolyzes slowly upon contact with water.

10.7.2 Reactive Group

Sulfonates, Phosphonates, and Thiophosphonates, Organic

10.7.3 Reactivity Alerts

Highly Flammable

10.7.4 Reactivity Profile

DIMETHYL METHYLPHOSPHONATE is incompatible with strong oxidizing agents and strong bases. It reacts with organic halides at 302-392 °F. When heated to temperatures greater than 302 °F, it will act as an alkylating agent with basic nitrogen compounds and phenols. It reacts with enol lactones. This compound has plasticizing properties and may soften or deteriorate some plastics and elastomers (particularly vinyl-based resins, neoprene and natural rubbers) upon contact. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

10.8 Transport Information

10.8.1 DOT Label

Flammable Liquid

10.9 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Phosphonic acid, methyl-, dimethyl ester
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Phosphonic acid, methyl-, dimethyl ester: Does not have an individual approval but may be used under an appropriate group standard

10.9.1 Federal Drinking Water Guidelines

EPA 100 ug/L
USEPA/Office of Water; Federal-State Toxicology and Risk Analysis Committee (FSTRAC). Summary of State and Federal Drinking Water Standards and Guidelines (11/93) To Present

10.10 Other Safety Information

Chemical Assessment
IMAP assessments - Phosphonic acid, methyl-, dimethyl ester: Human health tier II assessment

10.10.1 Special Reports

Subcommittee on Flame-Retardant Chemicals, Committee on Toxicology, Board on Environmental Studies and Toxicology, National Research Council; Toxicological Risks of Selected Flame-Retardant Chemicals p.319 (2000) Available at http://www.nap.edu/catalog/9841.html as of October 7, 2008
DHHS/NTP; Toxicology & Carcinogenesis Studies of Dimethyl Methylphosphonate in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 323 (1987) NIH Publication No. 88-2579

11 Toxicity

11.1 Toxicological Information

11.1.1 EPA Provisional Peer-Reviewed Toxicity Values

Chemical Substance
Reference Dose (RfD), Chronic
6 x 10^-2 mg/kg-day
Reference Dose (RfD), Subchronic
6 x 10^-2 mg/kg-day
PPRTV Assessment
Weight-Of-Evidence (WOE)
Suggestive evidence of carcinogenic potential
Last Revision
2006

11.1.2 RAIS Toxicity Values

Oral Chronic Reference Dose (RfDoc) (mg/kg-day)
0.06
Oral Chronic Reference Dose Reference
PPRTV Current
Oral Subchronic Chronic Reference Dose (RfDos) (mg/kg-day)
0.06
Oral Subchronic Chronic Reference Dose Reference
PPRTV Current
Oral Slope Factor (CSFo)(mg/kg-day)^-1
0.0017
Oral Slope Factor Reference
PPRTV Current

11.1.3 Carcinogen Classification

NTP Technical Report
TR-323: Toxicology and Carcinogenesis Studies of Dimethyl Methylphosphonate (CASRN 756-79-6) in F344/N Rats and B6C3F1 Mice (Gavage Studies) (1987 )
Peer Review Date
Conclusion for Male Rat
Some Evidence Some Evidence
Conclusion for Female Rat
No Evidence No Evidence
Conclusion for Male Mice
Inadequate Experiment Inadequate Experiment
Conclusion for Female Mice
No Evidence No Evidence
Summary
Under the conditions of these 2-year gavage studies, there was some evidence of carcinogenic activity of dimethyl methylphosphonate for male F344/N rats as shown by increased incidences of tubular cell hyperplasia, tubular cell adenocarcinomas, hyperplasia of the transitional cell epithelium, and transitional cell papillomas of the kidney. There was an increased incidence of mononuclear cell leukemia in male rats at 1,000 mg/kg. Renal toxicity and decreased survival occurred in dosed male rats. There was no evidence of carcinogenic activity of dimethyl methylphosphonate for female F344/N rats given doses of 500 or 1,000 mg/kg. The study in male B6C3F1 mice was an inadequate study of carcinogenic activity because of decreased survival in both dosed groups. There was no evidence of carcinogenic activity for female B6C3F1 mice receiving dimethyl methylphosphonate at 1,000 mg/kg; decreased survival of female mice at 2,000 mg/kg made this group inadequate for determination of carcinogenic activity.

11.1.4 Acute Effects

11.1.5 Toxicity Data

LC50 (rat) > 26,100 mg/m3/1hr

11.1.6 Antidote and Emergency Treatment

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160-1

11.1.7 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ ... To investigate alpha(2u)-globulin accumulation in the kidney after dimethyl methylphosphonate (DMMP) and diethyl ethylphosphonate (DEEP), male and female Fischer-344 rats were administered DMMP or DEEP daily for five consecutive days by gavage. DMMP doses were 500- and 1,000-mg/kg body weight (bw); due to marked toxicity, daily DEEP dose of 50 and 100 mg/kg had to be used. Control rats received corn oil only and positive controls received five doses of 500-mg/kg bw trimethylpentane (TMP). Relative kidney weights were increased in male rats dosed with DMMP, DEEP, and TMP. Alpha(2u)-globulin in kidney cytosol was separated and quantified by capillary electrophoresis and by SDS-PAGE and Western blotting. In DMMP-, DEEP-, and TMP-treated rats, dose-dependent increases in the alpha(2u)-globulin content were observed by both methods in male, but not female rats. The increase of alpha(2u)-globulin accumulation was accompanied by the formation of protein droplets in the proximal tubules of male rats...
Blumbach K et al; Toxicol Sci 53 (1): 24-32 (2000)
/LABORATORY ANIMALS: Acute Exposure/ Four male and four female albino rabbits received a dermal application of 2000 mg/kg Fyrol DMMP to their abdominal skin, which was then wrapped for 24 hours. The skin at the application site was abraded on half the animals. After 24 hours, the binding was removed. The animals were observed for 14 days after which they underwent necropsy. There was no mortality in this study. All rabbits appeared normal thoughout the study, with no clinical signs of toxicity. At necropsy one rabbit showed pale lungs but the other nine animals appeared normal.
USEPA; High Production Volume Information System (HPVIS). Detailed Chemical Results Chemical Name: Phosphonic acid, methyl-, dimethyl ester (756-79-6). Available from, as of October 13, 2008: https://www.epa.gov/chemrtk/hpvis/index.html
/LABORATORY ANIMALS: Acute Exposure/ Six albino rabbits received a dermal application of 0.5 mg of dimethyl methylphosphonate to one abraded and one nonabraded skin site. The application sites were then covered for 24 hours. When unwrapped, the sites were examined at 24 and 72 hours for irritation. If irritation was present, it was scored according to Draize. Very slight irritation was observed at 24 and 72 hours.
USEPA; High Production Volume Information System (HPVIS). Detailed Chemical Results Chemical Name: Phosphonic acid, methyl-, dimethyl ester (756-79-6). Available from, as of October 13, 2008: https://www.epa.gov/chemrtk/hpvis/index.html
/LABORATORY ANIMALS: Acute Exposure/ Six albino rabbits received 0.5 mL of Fyrol DMMP applied to a previously shaven area of their skin. The skin at the application sites of the rabbits was abraded prior to the administration of the test substance. The sites were covered for 24 hours, after which they were uncovered and examined for irritation. The sites were scored for irritation according to Draize. ...There was no irritation at any of the application sites.
USEPA; High Production Volume Information System (HPVIS). Detailed Chemical Results Chemical Name: Phosphonic acid, methyl-, dimethyl ester (756-79-6). Available from, as of October 13, 2008: https://www.epa.gov/chemrtk/hpvis/index.html
For more Non-Human Toxicity Excerpts (Complete) data for DIMETHYL METHYLPHOSPHONATE (30 total), please visit the HSDB record page.

11.1.8 Non-Human Toxicity Values

LD50 Rat (Sprague-Dawley male and female) oral >5000 mg/kg bw /Fyrol DMMP/
USEPA; High Production Volume Information System (HPVIS). Detailed Chemical Results Chemical Name: Phosphonic acid, methyl-, dimethyl ester (756-79-6). Available from, as of October 13, 2008: https://www.epa.gov/chemrtk/hpvis/index.html
LD50 Rabbit (albino male and female) dermal >2000 mg/kg bw /Fyrol DMMP/
USEPA; High Production Volume Information System (HPVIS). Detailed Chemical Results Chemical Name: Phosphonic acid, methyl-, dimethyl ester (756-79-6). Available from, as of October 13, 2008: https://www.epa.gov/chemrtk/hpvis/index.html
LC50 Rat (Sprague-Dawley male and female) inhalation >26.1 mg/L/1 hr
USEPA; High Production Volume Information System (HPVIS). Detailed Chemical Results Chemical Name: Phosphonic acid, methyl-, dimethyl ester (756-79-6). Available from, as of October 13, 2008: https://www.epa.gov/chemrtk/hpvis/index.html

11.1.9 Ongoing Test Status

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=756-79-6]

11.1.10 National Toxicology Program Studies

Dimethyl methylphosphonate (98% pure) is one of four chemicals nominated by the U.S. Army for toxicology and carcinogenesis studies because it was being considered for use to simulate the physical and spectroscopic (but not the biologic) properties of anticholinesterase (nerve) agents. Dimethyl methylphosphonate is also used as a flame retardant, a preignition additive for gasoline, an antifoam agent, a plasticizer and stabilizer, a textile conditioner and antistatic agent, and an additive for solvents and low-temperature hydraulic fluids. The United States produces 0.2-2 million pounds (91,000-910,000 kg) of per year. Gavage was chosen as the route of administration for all four candidate "simulants" to mimic potential exposure. ... In the 2-year studies, dimethyl methylphosphonate was administered in corn oil by gavage at doses of 0, 500, or 1,000 mg/kg/day to groups of 50 F344/N rats of each sex and at 0, 1,000, or 2,000 mg/kg/day to groups of 50 B6C3F1 mice of each sex. All animals were dosed 5 days/wk for 103 weeks. Body Weight and Survival in the Two-Year Studies: Mean body weights of high dose male rats were 5%-10% lower than those of the vehicle controls between weeks 28 and 76 and were 10%-24% lower between weeks 80 and 104. Mean body weights of high dose female rats were 8%-12% lower than those of the vehicle controls after week 80. Survival of male rats was greater than 50% in all groups until week 80, and after this time, survival decreased in both groups, with the survival at the end of the study being 27/50 in vehicle control, 17/50 in low dose, and 4/50 in high dose groups. Survival of low dose female rats was comparable to that of the vehicle controls, but the final survival of high dose female rats was decreased (vehicle control, 30/50; low dose, 33/50; high dose, 23/50). No other compound-related clinical signs were observed. Mean body weights of high dose male mice were 7%-16% lower than those of the vehicle control males between weeks 36 and 76, and those of high dose female mice were 6%-12% lower between weeks 88 and 103. Decreased survival between weeks 23 and 45 in high dose male mice was associated with fighting. Seventeen high dose male and 22 high dose female mice died during week 45; these deaths were associated with the accidental administration of a dose mixture that had a concentration 34% greater than the targeted amount. Eleven low dose male mice died on the same day during week 77. By the end of the study, 29/50 vehicle control, 12/50 low dose, and 0/50 high dose male mice were alive; 41/50, 30/50, and 2/50 female mice survived to the end of the study. Renal Effects in the Two-Year Studies: Administration of dimethyl methylphosphonate to male rats increased the average severity of nephropathy and caused mineralization (calcification) of the collecting tubules in the renal papilla (12/50; 41/50; 36/49), hyperplasia of the transitional epithelium lining the renal pelvis and overlying the renal papilla (0/50; 23/50; 21/49), and focal hyperplasia of the renal tubular epithelium (0/50; 8/50; 9/49). Administration of dimethyl methylphosphonate to male rats was also associated with the occurrence of rare renal tubular cell adenocarcinomas (0/50; 2/50; 3/49) and papillomas of the transitional epithelium lining of the renal pelvis (0/50; 2/50; 3/49); a transitional cell carcinoma occurred in a low dose male rat. There were no tubular cell or transitional cell neoplasms of the kidney in female rats. Hematopoietic System Effects in the Two-Year Studies: The incidence of mononuclear cell leukemia was increased in high dose male rats (10/50; 11/50; 17/50). ...Under the conditions of these 2-year gavage studies, there was some evidence of carcinogenic activity of dimethyl methylphosphonate for male F344/N rats as shown by increased incidences of tubular cell hyperplasia, tubular cell adenocarcinomas, hyperplasia of the transitional cell epithelium, and transitional cell papillomas of the kidney. There was an increased incidence of mononuclear cell leukemia in male rats at 1,000 mg/kg. Renal toxicity and decreased survival occurred in dosed male rats. There was no evidence of carcinogenic activity of dimethyl methylphosphonate for female F344/N rats given doses of 500 or 1,000 mg/kg. The study in male B6C3F1 mice was an inadequate study of carcinogenic activity because of decreased survival in both dosed groups. There was no evidence of carcinogenic activity for female B6C3F1 mice receiving dimethyl methylphosphonate at 1,000 mg/kg; decreased survival of female mice at 2,000 mg/kg made this group inadequate for determination of carcinogenic activity.
Toxicology & Carcinogenesis Studies of Dimethyl Methylphosphonate in F344/N Rats and B6C3F1 Mice (Gavage Studies). Technical Report Series No. 323 (1987) NIH Publication No. 88-2579 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709
In the single-administration studies, dimethyl methylphosphonate was given to rats and mice at doses up to 6,810 mg/kg body weight. No compound-related deaths were seen in male or female rats or male mice; two high dose female mice died. Rats exhibited inactivity, unsteady gait, and prostration after dosing; mice were inactive after dosing.
Toxicology & Carcinogenesis Studies of Dimethyl Methylphosphonate in F344/N Rats and B6C3F1 Mice (Gavage Studies). Technical Report Series No. 323 (1987) NIH Publication No. 88-2579 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709
Rats and mice received doses of 0, 1,250, 2,500, 5,000, 10,000, or 15,000 mg/kg dimethyl methylphosphonate/day /for 15 days/. Compound-related deaths occurred in the three highest dose groups of rats and the two highest dose groups of mice. Rats receiving doses of 2,500 mg/kg or higher were inactive and at 5,000 or 10,000 mg/kg had an unsteady gait after dosing; mice exhibited inactivity, shallow breathing, and prostration at doses of 10,000 mg/kg or higher. No lesions were reported in rats. Nonneoplastic lesions of the stomach were seen in some male mice at doses of 1,250 mg/kg and higher and in some female mice at doses of 5,000 mg/kg and higher.
Toxicology & Carcinogenesis Studies of Dimethyl Methylphosphonate in F344/N Rats and B6C3F1 Mice (Gavage Studies). Technical Report Series No. 323 (1987) NIH Publication No. 88-2579 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709
Dimethyl methylphosphonate was given at doses up to 8,000 mg/kg/day. Compound-related deaths occurred at 2,000, 4,000, and 8,000 mg/kg in rats and at 4,000 and 8,000 mg/kg in mice. Mean body weights of rats at 1,000 mg/kg and mice at 2,000 mg/kg were similar to those of the vehicle controls; decreased weight gain was seen at higher doses. No compound-related clinical signs were reported. Minimal to mild renal and testicular lesions were seen at all doses in male rats, but the severity of these lesions did not increase with increasing dose of the chemical. No apparent target tissues were identified in female rats or male and female mice.
Toxicology & Carcinogenesis Studies of Dimethyl Methylphosphonate in F344/N Rats and B6C3F1 Mice (Gavage Studies). Technical Report Series No. 323 (1987) NIH Publication No. 88-2579 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709
For more National Toxicology Program Studies (Complete) data for DIMETHYL METHYLPHOSPHONATE (6 total), please visit the HSDB record page.

11.1.11 TSCA Test Submissions

Teratogenicity was evaluated in fertilized female Sprague Dawley rats (25/group) exposed orally by gavage to dimethyl methylphosphonate (in 2% sodium carboxymethylcellulose vehicle) at dose levels of 0, 100, 1000 or 2000 mg/kg on gestation days (GD) 6-15. Dams were sacrificed on GD 21. Significant differences were observed between treated and control animals in the following: decreased maternal body weight gain and feed consumption (high-dose group), and retarded fetal physiological growth (including decreased body weight and delay in skeletal maturation, mid- and high-dose group). No significant differences were observed between treated and control animals with respect to fetal malformations. In a supplementary study, fertilized female Sprague Dawley rats (25/group) exposed orally by gavage to dimethyl methylphosphonate (in 2% sodium carboxymethylcellulose vehicle) at dose levels of 0 or 2000 mg/kg on gestation days (GD) 6-15 and 2500 mg/kg on GD 6-10. Dams were sacrificed on GD 21. Significant differences were observed between treated and control animals in the following: decreased maternal body weight gain and feed consumption and retarded fetal physiological growth (including decreased body weight and delay in skeletal maturation) (both treatment levels). No significant differences were observed between treated and control animals in the following: gross malformations, visceral or skeletal anomalies.
CIBA-GEIGY Ltd.; Reproduction Study - FAT80 021/Methyl Methylphosphonate) (Test For Teratogenic or Embryotoxic Effects). (1978), EPA Document No. OTS-0784-0242-2, Fiche No. OTS0000242-2
The mutagenicity of dimethyl methylphosphonate was evaluated in Salmonella tester strains TA98, TA100, TA1535 and TA1537 (Ames Test), both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Dimethyl methylphosphonate, diluted in DMSO, was tested at concentrations up to 2025ug/plate using the plate incorporation technique. Dimethyl methylphosphonate did not cause a positive response in any tester strain with or without metabolic activation.
Ciba-Geigy LTD.; Salmonella/Mammalian-Microsome Mutagenicity Test, (1978), EPA Document No. FYI-OTS-0784-0242, Fiche No. OTS0000242-2
The mutagenicity of dimethyl methylphosphonate was evaluated in Salmonella tester strains TA1535 and TA1538 (Ames Test), both in the presence and absence of added metabolic activation by rat liver S9 fraction. Based on preliminary toxicity determinations, dimethyl methylphosphonate, diluted in DMSO, was tested at concentrations up to 50mg/plate using the plate incorporation technique. Dimethyl methylphosphonate did not cause a positive response in any tester strain with or without metabolic activation.
Inveresk Research International; Testing for Mutagenic Activity in Dimethyl Methylphosphonate, (1976), EPA Document No. FYI-OTS-0784-0242, Fiche No. OTS0000242-2

11.2 Ecological Information

11.2.1 Ecotoxicity Values

LC50; Species: Oncorhynchus mykiss (Rainbow trout); Conditions: static, 13.2-14.9 °C, pH 7.6-8.1, hardness 202- 216 mg/L as CaC03; Concentration: 2259 mg/L for 96 hr /99.4% purity/
USEPA; High Production Volume Information System (HPVIS). Detailed Chemical Results Chemical Name: Phosphonic acid, methyl-, dimethyl ester (756-79-6). Available from, as of October 13, 2008: https://www.epa.gov/chemrtk/hpvis/index.html

11.2.2 US EPA Regional Screening Levels for Chemical Contaminants

Resident Soil (mg/kg)
3.20e+02
Industrial Soil (mg/kg)
1.40e+03
Tapwater (ug/L)
4.60e+01
MCL (ug/L)
5.00e+00
Risk-based SSL (mg/kg)
9.60e-03
Oral Slope Factor (mg/kg-day)-1
1.70e-03
Chronic Oral Reference Dose (mg/kg-day)
6.00e-02
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Fraction of Contaminant Absorbed Dermally from Soil
0.1

11.2.3 US EPA Regional Removal Management Levels for Chemical Contaminants

Resident Soil (mg/kg)
1.10e+04
Industrial Soil (mg/kg)
1.40e+05
Tapwater (ug/L)
3.60e+03
MCL (ug/L)
5.00e+00
Oral Slope Factor (mg/kg-day)-1
1.70e-03
Chronic Oral Reference Dose (mg/kg-day)
6.00e-02
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Fraction of Contaminant Absorbed Dermally from Soil
0.1

11.2.4 Environmental Fate / Exposure Summary

Dimethyl methylphosphonate's production and use as a flame retardant, simulants for nerve agents, antifoam agent, plasticizer and stabilizer, textile conditioner and antistatic agent, a preignition additive for gasoline, and as an additive for solvents and low-temperature hydraulic fluid may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.962 mm Hg at 25 °C indicates dimethyl methylphosphonate will exist solely as a vapor in the atmosphere. Vapor-phase dimethyl methylphosphonate will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 2.8 days. Dimethyl methylphosphonate is not expected to be susceptible to direct photolysis by sunlight based upon data for a similar compound, diisopropyl methylphosphonate, which did not photolyze when exposed to light (>290 nm) for 232 hours in distilled water. If released to soil, dimethyl methylphosphonate is expected to have very high mobility based upon an estimated Koc of 11. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 1.3X10-6 atm-cu m/mole. Dimethyl methylphosphonate is not expected to volatilize from dry soil surfaces based upon a vapor pressure. Limited biodegradation data indicate that biodegradation is not an important fate process for dimethyl methylphosphonate. If released into water, dimethyl methylphosphonate is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 22 and 240 days, respectively. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis half-lives of 124 and 12.4 days at pH 7 and 9, respectively, suggest that hydrolysis may be an important environmental fate process. Occupational exposure to dimethyl methylphosphonate may occur through inhalation and dermal contact with this compound at workplaces where dimethyl methylphosphonate is produced or used. (SRC)

11.2.5 Artificial Pollution Sources

Dimethyl methylphosphonate's production and use as a flame retardant, simulants for nerve agents, antifoam agent, plasticizer and stabilizer, textile conditioner and antistatic agent, a preignition additive for gasoline, and as an additive for solvents and low-temperature hydraulic fluid(1) may result in its release to the environment through various waste streams(SRC). The compound is listed as a chemical weapons precursor and is regulated by the Chemical Waepons Convention.
(1) National Toxicology Program, Center for the Evaluation of Risk to Human Reproduction. NTP-CERHR Report on the Reproductive and Developmental Toxicity of Dimethyl Methylphosphonate Draft (September 22, 2004) pg 2. Available at https://ntp.niehs.nih.gov/ntp/Meetings/2004/3CERHR_short_review.pdf as of April 8, 2009.

11.2.6 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 11(SRC), determined from a log Kow of -0.61(2) and a regression-derived equation(3), indicates that dimethyl methylphosphonate is expected to have very high mobility in soil(SRC); however experiments show that dimethyl methylphosphonate adsorbs strongly to natural montmorillonite clay mineral(4). Volatilization of dimethyl methylphosphonate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Dimethyl methylphosphonate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.962 mm Hg(6). In environmental chamber studies, dimethyl methylphosphonate at initial concns in soil from 100-1000 ppm exhibited half-lives ranging from 0.2-60 days; average half-life was 12.4 days(7). The transport and/or degradation process responsible for the loss of dimethyl methylphosphonate was not determined. Limited biodegradation data indicate that biodegradation is not an important fate process in soil(8).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Krikorian SE et al; Quat Struct Act Relat 6:65-70 (1987)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990)
(4) Bowen JM et al; Environ Sci Technol 22:1178-81 (1988)
(5) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(6) Boublik T et al; The Vapor Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region V17, Amsterdam, Netherlands: Elsevier Sci Publ (1984)
(7) Dynamac Corp; Chemical Hazard Information Profile dimethyl methylphosphonate Rockville Md (1983)
(8) McGrath JW et al; Lett Appl Microbiol 24: 69-73 (1997)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 11(SRC), determined from a log Kow of -0.61(2) and a regression-derived equation(3), indicates that dimethyl methylphosphonate is not expected to adsorb to suspended solids and sediment(SRC); however experiments show that dimethyl methylphosphonate adsorbs strongly to natural montmorillonite clay mineral(4). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.3X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 22 and 240 days, respectively(SRC). Dimethyl methylphosphonate will hydrolyze to methanol(6). Half-lives for dimethyl methylphosphonate are calculated to be 13.2 and 43.3 yrs at 20 and 10 °C, respectively, at unspecified pH(7). Hydrolysis acid, base and neutral rates for dimethyl methylphosphonate were reported as 1.36X10-9/mole-sec, 7.5X10-3/mole-sec, and 2.5X10-10/mole-sec, respectively(8). These rates correspond to half-lives of 3.27 yrs, 124 days, 12.4 days, and 1.2 days at pH 3, 7, 9, and 11, respectively(SRC). According to a classification scheme(9), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(10), suggests the potential for bioconcentration in aquatic organisms is low(SRC). In environmental chamber studies, dimethyl methylphosphonate half-lives in muddy water ranged from 7-210 days, removal mechanism for dimethyl methylphosphonate not specified(11). Limited biodegradation data indicate that biodegradation is not an important fate process in water(12).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Krikorian SE et al; Quat Struct Act Relat 6: 65-70 (1987)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990)
(4) Bowen JM et al; Environ Sci Technol 22:1178-81 (1988)
(5) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(6) Christol H et al; J Organometal Chem 12: 459-70 (1968)
(7) Belskii VE et al; Izv Akad Nauk SSSR Ser Khim 12: 2813-4 (1969)
(8) Mabey W, Mill T; J Phys chem Ref Data 7: 383-415 (1978)
(9) Franke C et al; Chemosphere 29: 1501-14 (1994)
(10) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(11) Dynamac Corp; Chemical Hazard Information Profile dimethyl methylphosphonate Rockville Md 1983)
(12) McGrath JW et al; Lett Appl Microbiol 24: 69-73 (1997)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethyl methylphosphonate, which has a vapor pressure of 0.962 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dimethyl methylphosphonate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.8 days(SRC), calculated from its rate constant of 5.7X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Dimethyl methylphosphonate is not expected to be susceptible to direct photolysis by sunlight based upon data for a similar compound, diisopropyl methylphosphonate, which did not photolyze when exposed to light (>290 nm) for 232 hours in distilled or Rocky Mountain Arsenal water(4).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(4) Spanggord RJ et al; Studies of Environmental fates of DIMP and DCPD USNTIS AD-A078236 (1979)

11.2.7 Environmental Biodegradation

AEROBIC: Dimethyl methylphosphonate was not used as a source of phosphorous or carbon by microorganisms and no organic phosphorous was released from mixed culture tests(1).
(1) McGrath JW et al; Lett Appl Microbiol 24: 69-73 (1997)

11.2.8 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of dimethyl methylphosphonate with photochemically-produced hydroxyl radicals has been estimated as 5.7X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.8 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Dimethyl methylphosphonate will hydrolyze to methanol(2). Half-lives for dimethyl methylphosphonate are calculated to be 13.2 and 43.3 years at 20 and 10 °C, respectively at unspecified pH(3). These two half-lives were calculated from kinetic data collected at 98, 90 and 80 °C(3). Hydrolysis acid, base and neutral rates for dimethyl methylphosphonate were reported as 1.36X10-9/mole-sec, 7.5X10-3/mole-sec, and 2.5X10-10/mole-sec, respectively(4). These rates correspond to half-lives of 3.27 yrs, 124 days, 12.4 days, and 1.2 days at pH 3, 7, 9, and 11, respectively(SRC). Dimethyl methylphosphonate is not expected to be susceptible to direct photolysis by sunlight based upon data for a similar compound, diisopropyl methylphosphonate, which did not photolyze when exposed to light (>290 nm) for 232 hours in distilled or Rocky Mountain Arsenal water(5).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Christol H et al; J Organometal Chem 12:459-70 (1968)
(3) Belskii VE et al; Izv Akad Nauk SSSR Ser Khim 12: 2813-4 (1969)
(4) Mabey W, Mill T; J Phys chem Ref Data 7: 383-415 (1978)
(5) Spanggord RJ et al; Studies of environental fates of DIMP and DCPD USNTIS AD-A078236 (1979)

11.2.9 Environmental Bioconcentration

An estimated BCF of 3 was calculated in fish for dimethyl methylphosphonate(SRC), using a log Kow of -0.61(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
(1) Krikorian SE et al; Quat Struct Act Relat 6: 65-70 (1987)
(2) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

11.2.10 Soil Adsorption / Mobility

The Koc of dimethyl methylphosphonate is estimated as 11(SRC), using a log Kow of -0.61(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dimethyl methylphosphonate is expected to have very high mobility in soil; however experiments show that dimethyl methylphosphonate adsorbs strongly to natural montmorillonite clay mineral(4).
(1) Krikorian SE et al; Quat Struct Act Relat 6: 65-70 (1987)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990)
(3) Swann RL et al; Res Rev 85: 17-28 (1983)
(4) Bowen JM et al; Environ Sci Technol 22: 1178-81 (1988)

11.2.11 Volatilization from Water / Soil

The Henry's Law constant for dimethyl methylphosphonate is estimated as 1.3X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dimethyl methylphosphonate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 22 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 240 days(SRC). Dimethyl methylphosphonate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Dimethyl methylphosphonate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.962 mm Hg(3).
(1) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) Boublik T et al; The Vapor Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region V17, Amsterdam, Netherlands: Elsevier Sci Publ (1984)

11.2.12 Atmospheric Concentrations

SOURCE DOMINATED: Dimethyl methylphosphonate ambient air concns at three different locations near the edge of a hazardous liquid waste lagoon were 109,000, 10,600 and 2450 ng/cu m(1). Concns at two sites approximately 1 mile from this lagoon were 31 and 20 ng/cu m(1).
(1) Guzewich DC et al; Air sampling around a hazardous liquid surface impoundment; Air Pollut Control Assoc Proc 76 Ann Mtg 2: 83-24.1 p.14 (1983)

11.2.13 Probable Routes of Human Exposure

NIOSH (NOES Survey 1981-1983) has statistically estimated that 2135 workers (763 of these were female) were potentially exposed to dimethyl methylphosphonate in the US(1). Occupational exposure to dimethyl methylphosphonate may occur through inhalation and dermal contact with this compound at workplaces where dimethyl methylphosphonate is produced or used(SRC).
(1) NIOSH; NOES. National Occupational Exposure Survey conducted from 1981-1983. Estimated numbers of employees potentially exposed to specific agents by 2-digit standard industrial classification (SIC). Available at https://www.cdc.gov/noes/ as of Nov 2008

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Wiley References

12.6 Chemical Co-Occurrences in Literature

12.7 Chemical-Gene Co-Occurrences in Literature

12.8 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Biological Test Results

14.1 BioAssay Results

15 Classification

15.1 MeSH Tree

15.2 ChemIDplus

15.3 CAMEO Chemicals

15.4 UN GHS Classification

15.5 NORMAN Suspect List Exchange Classification

15.6 EPA DSSTox Classification

15.7 EPA TSCA and CDR Classification

15.8 EPA Substance Registry Services Tree

15.9 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAMEO Chemicals
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    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
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  3. CAS Common Chemistry
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    Phosphonic acid, P-methyl-, dimethyl ester
    https://www.epa.gov/chemical-data-reporting
  7. EPA Chemicals under the TSCA
    Phosphonic acid, P-methyl-, dimethyl ester
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  8. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  9. EPA Provisional Peer-Reviewed Toxicity Values (PPRTVs)
  10. European Chemicals Agency (ECHA)
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    https://echa.europa.eu/web/guest/legal-notice
    Dimethyl methylphosphonate
    https://chem.echa.europa.eu/100.010.957
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  12. Hazardous Substances Data Bank (HSDB)
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  18. EPA Regional Screening Levels for Chemical Contaminants at Superfund Sites
  19. Hazardous Chemical Information System (HCIS), Safe Work Australia
  20. NITE-CMC
    Phosphonic acid, methyl-, dimethyl ester - FY2006 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/06-imcg-1355e.html
    Dimethyl methylphosphonate - FY2018 (Revised classification)
    https://www.chem-info.nite.go.jp/chem/english/ghs/18-mhlw-2128e.html
  21. IUPAC Digitized pKa Dataset
  22. SpectraBase
    METHYLPHOSPHONIC ACID, DIMETHYL ESTER
    https://spectrabase.com/spectrum/Bjag4VZDSFa
    PHOSPHONIC ACID,METHYL-,DIMETHYL ESTER
    https://spectrabase.com/spectrum/21JrWYyazeh
    DIMETHYL METHYLPHOSPHONATE (CONTAINS <2% TRIMETHYL PHOSPHATE)
    https://spectrabase.com/spectrum/IaBjZ7ImIRP
    methylphosphonic acid, dimethyl ester
    https://spectrabase.com/spectrum/867PIx0fVTY
    PHOSPHONIC ACID, METHYL-, DIMETHYL ESTER
    https://spectrabase.com/spectrum/7X1klVfuev0
  23. Japan Chemical Substance Dictionary (Nikkaji)
  24. NIST Mass Spectrometry Data Center
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    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    Dimethyl methylphosphonate
    http://www.nist.gov/srd/nist1a.cfm
  25. NMRShiftDB
  26. NTP Technical Reports
    Dimethyl Methylphosphonate
    https://ntp.niehs.nih.gov/data/tr
  27. Springer Nature
  28. SpringerMaterials
  29. Thieme Chemistry
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  30. Wikidata
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    https://www.wikidata.org/wiki/Q417529
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  37. EPA Substance Registry Services
  38. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  39. PATENTSCOPE (WIPO)
  40. NCBI
CONTENTS