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1,1-Dichloroacetone

PubChem CID
10567
Structure
1,1-Dichloroacetone_small.png
1,1-Dichloroacetone_3D_Structure.png
Molecular Formula
Synonyms
  • 1,1-Dichloroacetone
  • 513-88-2
  • 1,1-Dichloro-2-propanone
  • 1,1-DICHLOROPROPANONE
  • 2-Propanone, 1,1-dichloro-
Molecular Weight
126.97 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-04

1 Structures

1.1 2D Structure

Chemical Structure Depiction
1,1-Dichloroacetone.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,1-dichloropropan-2-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C3H4Cl2O/c1-2(6)3(4)5/h3H,1H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CC(=O)C(Cl)Cl
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C3H4Cl2O
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

513-88-2
30605-38-0

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 HMDB ID

2.3.7 Nikkaji Number

2.3.8 NSC Number

2.3.9 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1,1-dichloro-2-propanone
  • 1,1-dichloroacetone
  • 1,1-dichloropropanone

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
126.97 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
1.3
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
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
125.9639201 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
125.9639201 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
17.1Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
6
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
59.8
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 Boiling Point

120 °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. 4473

3.2.2 Solubility

Sol in ethyl alcohol; miscible in ethyl ether
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. 4473

3.2.3 Density

1.304 g/cu cm at 18 °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. 4473

3.2.4 Vapor Pressure

27 mm Hg at 25 °C
Ohe S; Computer Aided Data Book of Vapor Pressure. Tokyo, Japan: Data Book Publ Co (1976)

3.2.5 Decomposition

When heated to decomposition it emits toxic vapors of /hydrogen chloride/.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1214

3.2.6 Dissociation Constants

3.2.7 Kovats Retention Index

Standard non-polar
707.2, 714, 709.7, 705, 707

3.2.8 Other Experimental Properties

Boiling with sodium carbonate gives acrylic acid
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 537

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Volatile Organic Compound (VOC)

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
227145
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 2
Source of Sample
Fluka AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
VARIAN CFT-20
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 6
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
Unknown
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

43 99.99

27 7.50

83 2.60

26 2.30

63 2.20

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 6
View All
NIST Number
238583
Library
Main library
Total Peaks
54
m/z Top Peak
43
m/z 2nd Highest
15
m/z 3rd Highest
27
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4.2.2 Other MS

1 of 2
Other MS
MASS: 34161 (NIST/EPA/MSDC Mass Spectral database, 1990 version); 526 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
2 of 2
Authors
SASAKI S, TOYOHASHI UNIV. OF TECH.
Instrument
Unknown
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Top 5 Peaks

43 999

27 75

83 26

26 23

63 22

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.3 UV Spectra

UV: 1-10 (Phillip et al; Organic Electronic Spectral Data. John Wiley & Sons, New York)
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. 4473

4.4 IR Spectra

4.4.1 FTIR Spectra

1 of 2
Technique
CAPILLARY CELL: NEAT
Source of Sample
Fluka Chemie AG, Buchs, Switzerland
Catalog Number
35038
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
Neat
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
227145
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
227145
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 Near IR Spectra

1 of 2
Instrument Name
INSTRUMENT PARAMETERS=INST=BRUKER,RSN=10583,REO=2,CNM=HEI,ZFF=2
Technique
NIR Spectrometer= BRUKER IFS 88
Source of Spectrum
Prof. Buback, University of Goettingen, Germany
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
INSTRUMENT PARAMETERS=INST=BRUKER,RSN=10583,REO=2,CNM=HEI,ZFF=2
Technique
NIR Spectrometer= BRUKER IFS 88
Source of Spectrum
Prof. Buback, University of Goettingen, Germany
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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4.4.4 Vapor Phase IR Spectra

Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
227145
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.5 Raman Spectra

Catalog Number
227145
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 Absorption, Distribution and Excretion

... Dermal absorption of two haloketones (1,1-dichloropropanone and 1,1,1-trichloropropanone) and chloroform while bathing, /were examined/ by collecting and analyzing time profiles of expired breath samples of six human subjects during and following a 30-min bath. The disinfection byproduct concentrations in breath increased towards a maximum concentration during bathing. The maximum haloketone breath concentration during dermal exposure ranged from 0.1 to 0.9 ug /cu m, which was approximately two orders of magnitude lower than the maximum chloroform breath concentration during exposure. Based on a one-compartment model, the in vivo permeability of chloroform, 1,1-dichloropropanone, and 1,1,1-trichloropropanone were approximated to be 0.015, 7.5 x 10- 4, and 4.5 x 10- 4 cm /hr, respectively. Thus, haloketones are much less permeable across human skin under normal bathing conditions than is chloroform...
Xu X, Weisel CP; J Expo Anal Environ Epidemiol 15 (4): 289-96 (2005)

8 Use and Manufacturing

8.1 General Manufacturing Information

Disinfection byproducts are formed when disinfectants used in water treatment plants react with bromide and/or natural organic matter (i.e., decaying vegetation) present in the source water. /Disinfection byproducts/
US EPA; Disinfection Byproducts: A Reference Source, February 1, 2008. Available from, as of July 8, 2008: https://www.epa.gov/enviro/html/icr/gloss_dbp.html

9 Identification

9.1 Analytic Laboratory Methods

Method: EPA-NERL 524.2; Procedure: gas chromatography/mass spectrometry; Analyte: 1,1-dichloroacetone; Matrix: surface water, ground water, and drinking water in any stage of treatment; Detection Limit: 1 ug/L.
National Environmental Methods Index; Analytical, Test and Sampling Methods. Available from, as of October 14, 2008: https://www.nemi.gov
Method: EPA-OGWDW/TSC 551.1; Procedure: gas chromatography with electron capture detector; Analyte: 1,1-dichloroacetone; Matrix: finished drinking water, drinking water during intermediate stages of treatment, and raw source water; Detection Limit: 0.002 ug/L.
National Environmental Methods Index; Analytical, Test and Sampling Methods. Available from, as of October 14, 2008: https://www.nemi.gov

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Flammable
Corrosive
Acute Toxic
Irritant
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H226 (97.3%): Flammable liquid and vapor [Warning Flammable liquids]

H301 (62.7%): Toxic if swallowed [Danger Acute toxicity, oral]

H302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral]

H314 (36%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

H318 (36%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H319 (10.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H400 (33.3%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (33.3%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P273, P280, P301+P316, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P321, P330, P337+P317, P363, P370+P378, P391, 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 75 reports by companies from 7 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 (97.3%)

Acute Tox. 3 (62.7%)

Acute Tox. 4 (33.3%)

Skin Corr. 1B (36%)

Eye Dam. 1 (36%)

Eye Irrit. 2 (10.7%)

Aquatic Acute 1 (33.3%)

Aquatic Chronic 1 (33.3%)

10.2 Accidental Release Measures

10.2.1 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.

10.3 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 2-Propanone, 1,1-dichloro-
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
1,1-Dichloroacetone: Does not have an individual approval but may be used under an appropriate group standard

11 Toxicity

11.1 Toxicological Information

11.1.1 USGS Health-Based Screening Levels for Evaluating Water-Quality

Chemical
1,1-Dichloro-2-propanone
Chemical Classes
Volatile Organic Compound (VOC)
Reference
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

11.1.2 Acute Effects

11.1.3 Antidote and Emergency Treatment

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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Ketones and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 270
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 necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . For 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. Administer activated charcoal ... . /Ketones and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 270-1
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 if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ketones and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 271

11.1.4 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Groups of 10 male and 10 female Sprague-Dawley rats were administered 1,1-dichloro-2-propanone in corn oil by gavage at 0, 10, 20, 40, or 80 mg/kg/day for 90 consecutive days. Food and water consumption, body and organ weights, organ-to-body weight ratios, hematology, and clinical chemistry parameters were determined. Gross and microscopic pathology examinations also were conducted. No treatment-related mortality was observed during the study; however, liver, forestomach, and kidney toxicity was evident. Liver changes consisted of cytoplasmic alteration, cytomegaly, karyomegaly, and bile duct hyperplasia. These occurred with significance of p < or = 0.05 at or above 10 mg/kg/day in both sexes. The forestomach lesions included hyperkeratosis and epithelial hyperplasia in both sexes at 40 and 80 mg/kg/day, and ulcerations at 80 mg/kg/day. Also, an increased incidence and severity of spontaneously occurring chronic progressive nephropathy was most apparent in high dose males. Increases in organ-to-body weight ratios were noted for the liver and kidneys in females at the highest dose level and in males at the two highest dose levels. Serum enzymes (ALT, AST, and LDH) were increased in females and decreased in males. Based on liver lesions and biochemical changes, it was concluded that there was no experimentally definable NOAEL.
Daniel FB et al; Drug Chem Toxicol 16 (3): 293-305 (1993)
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Several chlorinated acetones have been identified in drinking water and these, as well as a number of chlorinated acroleins, are produced by chlorination of humic acid solutions. Many of these chlorinated compounds and the brominated acrolein analog were positive in the Ames Assay in the laboratory. To determine if carcinogenic activity was associated with these chemicals the following acetone derivatives: monochloro (MCA); 1,1-dichloro (1,1-DCA), 1,3-dichloro (1,3-DCA), 1,1,1-trichloro (1,1,1-TCA), 1,1,3-trichloro (1,1,3-TCA), and substituted acroleins: 2-chloro (CAC), 3,3-dichloro (DCAC), 2,3,3-trichloro (TCAC) and 2-bromo (BAC), were applied topically to SENCAR mice (25, 30, or 40/group) at the following dose levels: 50 mg/kg (MCA and 1,1,3-TCA); 50, 75 and 100 mg/kg (1,3-DCA); 100, 200 and 400 mg/kg (CAC, DCAC, and TCAC); 200 and 300 mg/kg (BAC); and 400, 600, and 800 mg/kg (1,1-DCA, and 1,1,1-TCA). Doses were applied six times over a 2-week period in 0.2 mL ethanol per application. 1,3-DCA was also tested with single doses of 37.5, 75, 150 and 300 mg/kg in 0.2 mL ethanol. Control animals received 0.2 mL ethanol per application as a single dose or multiple doses to match corresponding studies. Two weeks after the final dose, 1.0 ug TPA in 0.2 mL acetone was applied three times weekly for 20 weeks. After 24 weeks the percentage of animals with tumors for dose groups above were: MCA (8); 1,1,3-TCA (10); 1,3-DCA, multiple doses (48, 45, 32); CAC (30, 28, 38); DCAC (3, 0, 0); TCAC (10, 5, 0); BAC (54, 43); 1,1-DCA (0, 5, 0); 1,1,1-TCA (10, 5, 0); 1,3-DCA, single doses (47, 47, 63, 20); controls (12 ... , 9 ... average). These data show that 1,3-DCA, CAC and BAC, when applied topically, initiate tumors in the mouse skin. These chemicals administered orally in a 2% emulphor solution ... did not initiate tumors in the mouse skin. /Chlorinated acetones and acroleins/
Robinson M et al; Cancer Lett 48 (3): 197-203 (1989)
/GENOTOXICITY/ Mutagenic potencies among the chloropropanones in Salmonella typhimurium bacteria differed greatly. 1,3-dichloropropanone (1,3-DCP) was mutagenic in the nanomole range, 1,1-dichloropropanone (1,1-DCP) was weakly mutagenic in the micromole range, and monochloropropanone (MCP), was not mutagenic. Mutagenicity of the dichloropropanones was evident without metabolic activation. ... /Chloropropanones/
Merrick BA et al; Toxicol Appl Pharmacol 91 (1): 46-54 (1987)
/GENOTOXICITY/ Soil humic substances were chlorinated in solution, extracted with ether and subjected to mutagenicity assay. Mutagenicity was detected using Salmonella typhimurium TA 100, with or without S9 mix; mutagenic activity was found to be less with added S9 mix. Ether extracts were analyzed by gas chromatography-mass spectrometry (GC-MS) and various chlorinated and non-chlorinated compounds were detected, e.g. chlorinated esters, acetones and carboxylic acids, as well as non-chlorinated aromatics. The mutagenicity of the major chlorination products was examined. Chloral and 1,1,1,3,3-pentachloro-2-propanone (pentachloroacetone) were found to be mutagenic, and 1,1-dichloro-2-propanone (1,1-dichloroacetone) was a possible mutagen. The yields of these mutagens increased with an increase in chlorine concentration.
Sato T et al; Sci Total Environ 46: 229-41 (1985)
For more Non-Human Toxicity Excerpts (Complete) data for 1,1-DICHLOROACETONE (6 total), please visit the HSDB record page.

11.2 Ecological Information

11.2.1 Environmental Fate / Exposure Summary

1,1-Dichloroacetone's fromation as a result of chlorine disinfection of drinking water may result in its release to the environment through various waste streams. Disinfection byproducts are formed when chlorine or other disinfectants, which are used to control contaminants in drinking water, react with naturally occurring organic and inorganic matter present in water. If released to air, a vapor pressure of 27 mm Hg at 25 °C indicates 1,1-dichloroacetone will exist solely as a vapor in the atmosphere. Vapor-phase 1,1-dichloroacetone 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 61 days. 1,1-Dichloroacetone contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight. If released to soil, 1,1-dichloroacetone is expected to have very high mobility based upon an estimated Koc of 6.0. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 6.1X10-6 atm-cu m/mole. 1,1-Dichloroacetone may volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data were not available. If released into water, 1,1-dichloroacetone 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 7 and 53 days, respectively. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Monitoring data indicate that the general population may be exposed to 1,1-dichloroacetone via ingestion of chlorine-treated drinking water. (SRC)

11.2.2 Artificial Pollution Sources

1,1-Dichloroacetone's formation as a result of chlorine disinfection of drinking water(1) may result in its release to the environment through various waste streams(SRC).
(1) US EPA; Disinfection Byproducts: A Reference Source, February 1, 2008. Available at https://www.epa.gov/enviro/html/icr/gloss_dbp.html as of July 8, 2008.

11.2.3 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6.0(SRC), determined from a structure estimation method(2), indicates that 1,1-dichloroacetone is expected to have very high mobility in soil(SRC). Volatilization of 1,1-dichloroacetone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.15X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 1,1-Dichloroacetone is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 27 mm Hg(4). Biodegradation data were not available(SRC, 2008).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(4) Ohe S; Computer Aided Data Book of Vapor Pressure. Tokyo, Japan: Data Book Publ Co (1976)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6.0(SRC), determined from a structure estimation method(2), indicates that 1,1-dichloroacetone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 6.1X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7 days and 53 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.20(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Biodegradation data were not available(SRC, 2008).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(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) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(5) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(6) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,1-dichloroacetone, which has a vapor pressure of 27 mm Hg at 25 °C(2) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,1-dichloroacetone 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 61 days(SRC), calculated from its rate constant of 2.6X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1,1-Dichloroacetone contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Ohe S; Computer Aided Data Book of Vapor Pressure. Tokyo, Japan: Data Book Publ Co (1976)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 8-12 (1990)

11.2.4 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of 1,1-dichloroacetone with photochemically-produced hydroxyl radicals has been estimated as 2.6X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 61 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1,1-Dichloroacetone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). 1,1-Dichloroacetone contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Mill T et al; Environmental Fate and Exposure Studies Development of a PC-SAR for Hydrolysis: Esters, Alkyl Halides and Epoxides. EPA Contract No. 68-02-4254. Menlo Park, CA: SRI International (1987)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12 (1990)
1,1-Dichloroacetone was measured to decompose in fortified drinking water solutions with a rate constant of 0.022 hr-1 at 21 °C, half-life of 32 hrs and 0.071 hr-1 at 30 °C, half-life of 10 hrs(1). A rate constant of 0.010 hr-1 at 30 °C was measured in an ultrapure water solution indicating a half-life of 69 hrs(1). Chloroform, a degradation product, forms more rapidly in ultrapure water solutions than in fortified drinking water; this indicates that the decomposition of 1,1-dichloroacetone may lead to products other than chloroform such as chloral hydrate when decomposed in drinking water(1).
(1) Nikolaou AD, et al; Chemosphere 44: 907-912 (2001)

11.2.5 Environmental Bioconcentration

An estimated BCF of 3 was calculated for 1,1-dichloroacetone(SRC), using an estimated log Kow of 0.20(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) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(2) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

11.2.6 Soil Adsorption / Mobility

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1,1-dichloroacetone can be estimated to be 6.0(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,1-dichloroacetone is expected to have very high mobility in soil.
(1) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(2) Swann RL et al; Res Rev 85: 17-28 (1983)

11.2.7 Volatilization from Water / Soil

The Henry's Law constant for 1,1-dichloroacetone is estimated as 6.1X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1,1-dichloroacetone 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 7 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 53 days(SRC). 1,1-Dichloroacetone's Henry's Law constant indicates that volatilization from moist soil surfaces may exist(SRC). 1,1-Dichloroacetone is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 27 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) Ohe S; Computer Aided Data Book of Vapor Pressure. Tokyo, Japan: Data Book Publ Co (1976)

11.2.8 Environmental Water Concentrations

GROUNDWATER: 1,1-Dichloroacetone was detected at a concentration of 15 ug/L in a groundwater sample from the Tres Rios area, in Phoenix, Arizona(1).
(1) Rostad CE et al; Environ Sci Tech 34: 2703-10 (2000)
DRINKING WATER: 1,1-Dichloroacetone was detected in drinking water at a concentration of 1.4 ug/L as a disinfection by-product of hypochlorous acid(1). 1,1-Dichloroacetone was detected at median concentrations of 0.52 ug/L (spring), 0.46 ug/L (summer), 0.52 ug/L (autumn), 0.55 ug/L (winter) in 35 United States drinking waters during quarterly periods in 1988(2). 1,1-Dichloroacetone was detected in tap water at a concentration of 50 ug/L after tertiary water treatment in Phoenix, Arizona, July 1997(3).
(1) Bull RJ et al; Disinfect Dilemma. Denver, CO: Amer Water Works Assoc, pp. 221-39 (1993)
(2) Krasner SW, et al; J Amer Water Works Assoc 81: 41-53 (1989)
(3) Rostad CE et al; Environ Sci Tech 34: 2703-10 (2000)
SURFACE WATER: Water samples from the Tres Rios Wetlands in Arizona, which receives tertiary treated sewage effluent from 91st Ave Wastewater Treatment Plant, were collected in July 1997 to examine the fate of disinfection by-products in wetlands(1). 1,1-Dichloroacetone was detected at concentrations of 3.2 ug/L (Salt River flood plain inlet), 3.6 ug/L (Hayfield site wetland inlet), and 3.2 ug/L (open water research cell 1 inlet)(1). A concentration of 0.1 ug/L was reported for the Gila River, Arizona(1). 1,1-Dichloroacetone was identified, not quantified, in the River Glatt, Switzerland using gas chromatography-mass spectrometry(2).
(1) Rostad CE et al; Environ Sci Tech 34: 2703-10 (2000)
(2) Zuercher F, Giger W; Vom Wasser 47: 37-55 (1976)

11.2.9 Effluent Concentrations

1,1-Dichloroacetone was detected in spent chlorination liquor from bleaching sulphite pulp at 0.1 g/ ton pulp with a high lignin content and at 0.3 g/ ton pulp with a normal lignin content after oxygen treatment, based on analysis using gas chromatography-mass spectrometry(1). The compound was detected, not quantified, during bleaching processes of kraft pulp for hardwoods and softwoods with chlorine dioxide(2). It was detected during processing of hardwood pulp at stages of acid filtration and at a combined sewer of the bleaching plant(2). It was also detected during processing of softwood pulp at stages of acid filtration and influent to the wastewater treatment plant before secondary clarifiers(2). Water from the Llobegat River in Barcelona was tested at three stages of a treatment process in a water treatment plant from Nov 1997 to Mar 1998. 1,1-Dichloroacetone was detected during prechlorination, sand filtration, ozonization, and post-chlorination at concentrations of 0.4 ug/L, 0.2 ug/L, 0.3 ug/L, and 0.1 ug/L, using the modified EPA Method 551.1(3). Several mass spectrometry techniques and IR spectroscopy were used in identification, not quantification, of 1,1-dichloroacetone after ozone-chlorine or ozone-chloramine disinfection at a pilot plant in Jefferson Parish, LA using the Mississippi River as a raw water source between Jan 1994 and Sept 1996(4). Identification of 1,1-dichloroacetone was confirmed by analysis of authentic standards, and was reported only when detected at concentrations at least 2 to 3 times what it was in raw, untreated water(4). Three Canadian water treatment plants using different disinfection processes were monitored monthly over a year-long period at varying points along each plants' distribution system(5). 1,1-Dichloroacetone was detected at mean concentrations of 1.8 ug/L (at facility directly after disinfection), 1.8 ug/L (3 km from plant), 1.3 ug/L (10 km from plant), 1.3 ug/L (18 km from plant) and at a minimum concentration of <0.1 ug/L and maximum concentration of 2.8 ug/L(5). 1,1-Diloroacetone was detected at concentrations of 29 ug/L at and 12 ug/L in waste water treatment plant effluents from plants at 91st Ave and 115th Ave, respectively, in Phoenix, Arizona(6).
(1) Carlberg GE et al; Sci Total Environ 48: 157-67 (1986)
(2) Jutti S et al; Chemosphere 33: 437-448 (1996)
(3) Cancho B et al; Bull Environ Contam 63: 610-17 (1999)
(4) Richardson SD et al; Environ Sci Technol 33: 3368-77 (1999)
(5) Lebel GL et al; Chemosphere 34: 2301-17 (1997)
(6) Rostad CE et al; Environ Sci Tech 34: 2703-10 (2000)

11.2.10 Probable Routes of Human Exposure

Monitoring data indicate that the general population may be exposed to 1,1-dichloroacetone via ingestion of chlorine-treated drinking water.(SRC)

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 UN GHS Classification

15.4 NORMAN Suspect List Exchange Classification

15.5 EPA DSSTox Classification

15.6 EPA Substance Registry Services Tree

15.7 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DTP/NCI
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    https://www.cancer.gov/policies/copyright-reuse
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    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. European Chemicals Agency (ECHA)
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    https://echa.europa.eu/web/guest/legal-notice
  7. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  8. Hazardous Substances Data Bank (HSDB)
  9. New Zealand Environmental Protection Authority (EPA)
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    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  10. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  11. MassBank Europe
  12. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  13. IUPAC Digitized pKa Dataset
  14. Japan Chemical Substance Dictionary (Nikkaji)
  15. MassBank of North America (MoNA)
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    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  16. 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
    2-Propanone, 1,1-dichloro-
    http://www.nist.gov/srd/nist1a.cfm
  17. SpectraBase
  18. NMRShiftDB
  19. Springer Nature
  20. SpringerMaterials
  21. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  22. USGS Health-Based Screening Levels for Evaluating Water-Quality Data
  23. Wikidata
  24. Wiley
  25. PubChem
  26. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  27. GHS Classification (UNECE)
  28. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  29. EPA Substance Registry Services
  30. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  31. PATENTSCOPE (WIPO)
CONTENTS