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Triethylenediamine

PubChem CID
9237
Structure
Triethylenediamine_small.png
Triethylenediamine_3D_Structure.png
Molecular Formula
Synonyms
  • 1,4-Diazabicyclo[2.2.2]octane
  • Triethylenediamine
  • 280-57-9
  • Dabco
  • 1,4-DIAZABICYCLO(2.2.2)OCTANE
Molecular Weight
112.17 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2024-12-21
Description
Triethylenediamine is an organic heterobicylic compound that is piperazine with an ethane-1,2-diyl group forming a bridge between N1 and N4. It is typically used as a catalyst in polymerization reactions. It has a role as a catalyst, a reagent and an antioxidant. It is a bridged compound, a tertiary amino compound, a saturated organic heterobicyclic parent and a diamine.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Triethylenediamine.png

1.2 3D Conformer

1.3 Crystal Structures

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,4-diazabicyclo[2.2.2]octane
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

C1CN2CCN1CC2
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C6H12N2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

280-57-9

2.3.3 Deprecated CAS

101484-19-9, 1357848-51-1, 150605-01-9, 165724-47-0, 203072-11-1, 2260745-52-4, 23790-33-2, 309955-09-7, 682335-96-2, 746642-46-6, 88935-43-7, 903524-95-8
101484-19-9, 1354649-42-5, 1357848-51-1, 150605-01-9, 165724-47-0, 203072-11-1, 2260745-52-4, 23790-33-2, 309955-09-7, 682335-96-2, 746642-46-6, 88935-43-7, 903524-95-8
101484-19-9, 150605-01-9, 165724-47-0, 203072-11-1, 23790-33-2, 309955-09-7, 746642-46-6, 88935-43-7

2.3.4 European Community (EC) Number

2.3.5 UNII

2.3.6 ChEBI ID

2.3.7 ChEMBL ID

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 NSC Number

2.3.13 Pharos Ligand ID

2.3.14 Wikidata

2.3.15 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1,4-diazabicyclo(2.2.2)octane
  • 1,4-diazabicyclo-octane
  • DABCO
  • DABCO cpd
  • triethylenediamine
  • triethylenediamine diacetate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
112.17 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-0.2
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
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
112.100048391 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
112.100048391 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
6.5Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
8
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
61.5
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

Pellets or Large Crystals; Liquid; Other Solid
White crystals with an ammonia-like odour; Sublimes (goes directly from solid to vapour) readily at room temperature; Extremely hygroscopic (absorbs moisture from the air); [CHEMINFO]

3.2.2 Color / Form

Colorless hygroscopic crystals
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 1126

3.2.3 Boiling Point

174 °C
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. 1723

3.2.4 Melting Point

158 °C
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. 1723

3.2.5 Flash Point

62 °C

3.2.6 Solubility

13 g/100 g acetone at 25 °C; 51 g/100 g benzene at 25 °C; 77 g/100 g ethanol at 25 °C; 26.1 g/100 g methyl ethyl ketone at 25 °C
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. 1723
Soluble in chloroform
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-498
45 g/100 g water at 25 °C
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. 1723

3.2.7 Density

1.14 at 28 °C (Water = 1)[NITE; Chemical Risk Information Platform (CHRIP). Biodegradation and Bioconcentration. Ver 2006.01.30 Updated. National Institute of Technology and Evaluation. Tokyo, Japan. Thiodiethylene glycolBicyclo
2.2.2]octane, 1,4-diaza-. 280-57-9. Available from, as of Sept 6, 2006: https://www.safe.nite.go.jp/english/kizon/KIZON_start_hazkizon.html

3.2.8 Vapor Pressure

0.74 [mmHg]

3.2.9 Decomposition

When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1124

3.2.10 Heat of Vaporization

61.9 kJ/mol (heat of sublimation below 75 °C)
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V8: 76 (1993)

3.2.11 Dissociation Constants

pKa1 = 3.0; pKa2 = 8.7
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. 1723

3.2.12 Kovats Retention Index

Standard non-polar
1018, 1023, 1040
Standard polar
1520, 1531, 1535, 1548, 1548

3.2.13 Other Experimental Properties

Extremely hygroscopic; sublimes readily at room temperature
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. 1723
Hydroxyl radical reaction rate constant = 2.2X10-11 cu cm/molecule-sec at 25 °C
Koch R et al; Int J Chem Kinet 28: 807-15 (1996)

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Nitrogen Compounds -> Amines, Cyclic

4 Spectral Information

4.1 1D NMR Spectra

1 of 2
1D NMR Spectra
1H NMR: 4219 (Sadtler Research Laboratories Spectral Collection)
2 of 2
1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
BRUKER AC-300
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1991-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Varian A-60
Source of Sample
MCB MANUFACTURING CHEMISTS, NORWOOD, OHIO
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
Bruker WH-90
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 5
View All
NIST Number
228321
Library
Main library
Total Peaks
47
m/z Top Peak
42
m/z 2nd Highest
55
m/z 3rd Highest
112
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2 of 5
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NIST Number
62687
Library
Replicate library
Total Peaks
58
m/z Top Peak
42
m/z 2nd Highest
55
m/z 3rd Highest
112
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4.2.2 LC-MS

1 of 8
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Authors
F. Jud [dtc], K. Arturi [dtc], J. Hollender [dtc], A. Dax [com]
Instrument
Exploris 240 Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
15 % (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
0.717 min
Precursor m/z
113.1073
Precursor Adduct
[M+H]+
Top 5 Peaks
113.1071 999
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License
CC BY-SA
2 of 8
View All
Authors
F. Jud [dtc], K. Arturi [dtc], J. Hollender [dtc], A. Dax [com]
Instrument
Exploris 240 Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
30 % (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
0.717 min
Precursor m/z
113.1073
Precursor Adduct
[M+H]+
Top 5 Peaks
113.1071 999
Thumbnail
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License
CC BY-SA

4.2.3 Other MS

1 of 4
View All
Other MS
MASS: 72989 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
2 of 4
View All
Authors
EPA CCTE and Agilent Technologies
Instrument Type
ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10
Precursor m/z
113.1073248
Precursor Adduct
[M+H]+
Top 5 Peaks
113.107325 999
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License
CC BY

4.3 IR Spectra

IR Spectra
IR: 5517 (Coblentz Society Spectral Collection) /Bicyclo(2.2.2)octane, 1,4-diaza, dihydrochloride/
IR Spectra
IR: 5852 (Coblentz Society Spectral Collection)

4.3.1 FTIR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
KBr0
Source of Spectrum
Forensic Spectral Research
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
BETWEEN SALTS
Source of Sample
Jefferson Chemical Company, Inc., Houston, Texas
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.2 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
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2 of 2
Source of Sample
Aldrich
Catalog Number
290734
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.3 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
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2 of 2
Instrument Name
Bruker IFS 85
Technique
Gas-GC
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.4 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Company Llc.
Catalog Number
<a href=https://www.sigmaaldrich.com/US/en/product/sial/D27802>D27802</a>
Lot Number
5529EE
Copyright
Copyright © 2013-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Clinical Trials

7.1.1 ClinicalTrials.gov

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Radiation-Protective Agents
Drugs used to protect against ionizing radiation. They are usually of interest for use in radiation therapy but have been considered for other purposes, e.g. military. (See all compounds classified as Radiation-Protective Agents.)

9 Use and Manufacturing

9.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Used as curing agent for urethane foams; used as a singlet oxygen trap and a radioiodine trap; [HSDB]
Industrial Processes with risk of exposure
Catalyst in making urethane foams
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. 1723
The only important industrial use of triethylenediamine is as a hardener for polyurethane foams.
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V2 402 (2003)
Anti-fade reagent that scavenges free-radicals produced by excitation of fluorochromes. Added to the mounting medium in fluorescence microscopy to retard photobleaching of fluorescein and other fluorescent dyes.[Sigma-Aldrich; D2522 Sigma 1,4-Diazabicyclo
2.2.2]octane. Available from, as of November 22, 2006: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/D2522
Singlet oxygen trap used as diagnostic for singlet oxygen; trap for radioiodine
... Oxidation and polymerization catalyst, chemical intermediate (metal complexes, quaternary ammonium compounds, etc), bromide and iodine addition compounds.
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 1126

9.1.1 Industry Uses

  • Intermediates
  • Propellants and blowing agents
  • Absorbent
  • Pigment
  • Viscosity modifiers
  • Other (specify)
  • Catalyst
  • Process regulators

9.1.2 Consumer Uses

  • Other
  • Processing aids not otherwise specified
  • Paint additives and coating additives not described by other categories
  • Pigment
  • Other (specify)
  • Viscosity modifiers
  • Not Known or Reasonably Ascertainable

9.2 Methods of Manufacturing

KRAUSE ET AL, BRITISH PATENT 871,754 (1958 TO HOUDRY PROCESS).
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. 1723
Triethylenediamine can be produced from ethylenediamine or ethanolamine, diethanolamine, or diethylenetriamine with a variety of different catalysts.
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V2 402 (2003)

9.3 U.S. Production

Aggregated Product Volume

2019: 1,000,000 - <10,000,000 lb

2018: 1,000,000 - <10,000,000 lb

2017: 1,000,000 - <10,000,000 lb

2016: 1,000,000 - <10,000,000 lb

This chemical is listed as a High Production Volume (HPV) (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 on 1,4-Diazabicyclo(2.2.2) Octane (280-57-9). Available from, as of November 16, 2006: https://www.epa.gov/hpv/pubs/general/opptsrch.htm
Production volumes for non-confidential chemicals reported under the Inventory Update Rule.
Year
1986
Production Range (pounds)
>1 million - 10 million
Year
1990
Production Range (pounds)
>1 million - 50 million
Year
1994
Production Range (pounds)
>1 million - 10 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). 1,4-Diazabicyclo(2,2,2) Octane (280-57-9). Available from, as of November 7, 2006: https://www.epa.gov/oppt/iur/tools/data/2002-vol.html

9.4 General Manufacturing Information

Industry Processing Sectors
  • Plastics Product Manufacturing
  • Oil and Gas Drilling, Extraction, and Support activities
  • Construction
  • All Other Chemical Product and Preparation Manufacturing
  • Plastics Material and Resin Manufacturing
  • Petrochemical Manufacturing
  • Wholesale and Retail Trade
  • Miscellaneous Manufacturing
  • All Other Basic Organic Chemical Manufacturing
  • Paint and Coating Manufacturing
EPA TSCA Commercial Activity Status
Triethylenediamine is used to impregnate the activated carbon found in respiratory protection against chemical weapon agents.
CW Protective Equipment; An overview of respiratory and body protection. Available from, as of Sept 7, 2006: https://www.opcw.org/resp/html/equip.html
Certain low-molecular chemical weapon agents such as hydrogen cyanide and cyanogen chloride are poorly absorbed by active carbon. In order to improve protection against these substances, the carbon is impregnated with metallic salts of copper, chromium and sometimes silver. Further impregnation with organic substances also occurs, the most common additive being triethylenediamine.
OPCW; CW Protective Equipment. FOA Briefing Book on Chemical Weapons. Organization for the Prohibition of Chemical Weapons, The Hague, The Netherlands. Available from, as of Oct 18, 2006: https://www.opcw.org/resp/html/equip.html

10 Identification

10.1 Analytic Laboratory Methods

Gas chromatographic identification & separation of piperazine derivatives were achieved with good reproducibility.
GAS CHROMATOGRAPHY ANALYSIS OF N-METHYL-N'-AMINOPIPERAZINE AND SOME PIPERAZINE DERIVATIVES; FEN HSI HUA HSUEH 6(4) 247 (1978)
Method: NIOSH 2540, issue 2; Procedure: high performance liquid chromatography with ultraviolet detection; Analyte: naphthylisothiourea derivative of analytes; Matrix: air; Detection Limit: 0.9 ug per sample. /Ethylenediamine/
CDC; NIOSH Manual of Analytical Methods, 4th ed. Ethylenediamine (107-15-3). Available from, as of November 17, 2006: https://www.cdc.gov/niosh/docs/2003-154/

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

1 of 2
View All
Note
Pictograms displayed are for 99.2% (779 of 785) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 0.8% (6 of 785) of reports.
Pictogram(s)
Flammable
Corrosive
Irritant
Signal
Danger
GHS Hazard Statements

H228 (76.7%): Flammable solid [Danger Flammable solids]

H302 (96.4%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (97.2%): Causes skin irritation [Warning Skin corrosion/irritation]

H318 (44.1%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H319 (45.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (22.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H412 (20.4%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P210, P240, P241, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, 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 785 reports by companies from 42 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 6 of 785 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 41 notifications provided by 779 of 785 reports by companies with hazard statement code(s).

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.

11.1.2 Hazard Classes and Categories

Flam. Sol. 1 (76.7%)

Acute Tox. 4 (96.4%)

Skin Irrit. 2 (97.2%)

Eye Dam. 1 (44.1%)

Eye Irrit. 2 (45.1%)

STOT SE 3 (22.3%)

Aquatic Chronic 3 (20.4%)

Acute toxicity (Oral) - Category 4

Skin corrosion/irritation - Category 2

Serious eye damage/eye irritation - Category 2

Reproductive toxicity - Category 2

Specific target organ toxicity - Single exposure - Category 2 (central nervous system)

Specific target organ toxicity - Repeated exposure - Category 1 (upper respiratory tract)

11.1.3 Hazards Summary

Workers have reported visual disturbances--haloes around lights; [ACGIH] Corrosive to skin; [Quick CPC] Corrosive to skin and eyes; [CHEMINFO]
ACGIH - Documentation of the TLVs and BEIs, 7th Ed. Cincinnati: ACGIH Worldwide, 2020.
Quick CPC - Forsberg K, Mansdorf SZ. Quick Selection Guide to Chemical Protective Clothing, 5th Ed. Hoboken, NJ: Wiley-Interscience, 2007.

11.2 Accidental Release Measures

11.2.1 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.

11.3 Stability and Reactivity

11.3.1 Hazardous Reactivities and Incompatibilities

... In paint manufacture, preliminary small-scale (12 g) tests in which ethyl acetate soln of cellulose nitrate and the other components were mixed in a lagged boiling tube showed large exotherms (which boiled the solvent off) with 1,4-diazabicyclo(2.2.2)octane ... Subsequent test in which small portions of ... undiluted /1,4-diazabicyclo(2.2.2.)octane/ and dried cellulose nitrate linters were contacted (with a little added butyl acetate for the solid phenol) under various condition ... ignition /occurred/ ...
Bretherick, L. Handbook of Reactive Chemical Hazards. 4th ed. Boston, MA: Butterworth-Heinemann Ltd., 1990, p. 1536
Activated carbon showed an auto-ignition temp in flowing air of 452 to 518 °C. Presence of 5% of ... triethylenediamine adsorbed on the carbon reduced the autoignition temp (AIT) to 230 to 260 °C. At high air flow rates an exotherm was seen at 230 to 260 °C but ignition did not then occur until 500 °C.
Bretherick, L. Handbook of Reactive Chemical Hazards. 4th ed. Boston, MA: Butterworth-Heinemann Ltd., 1990, p. 111
A sample of the 1:1 complex /of 1.4-diazabicyclo(2.2.2)octane and hydrogen peroxide/exploded while being dried overnight in a desiccator.
Bretherick, L. Handbook of Reactive Chemical Hazards. 4th ed. Boston, MA: Butterworth-Heinemann Ltd., 1990, p. 650

11.4 Transport Information

11.4.1 DOT Emergency Guidelines

/GUIDE 133: FLAMMABLE SOLIDS/ Fire or Explosion: Flammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished. /Flammable solid, organic, NOS (1,4-Diazabicyclo(2.2.2)octane)/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
/GUIDE 133: FLAMMABLE SOLIDS/ Health: Fire may produce irritating and/or toxic gases. Contact may cause burns to skin and eyes. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution. /Flammable solid, organic, NOS (1,4-Diazabicyclo(2.2.2)octane)/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
/GUIDE 133: FLAMMABLE SOLIDS/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 25 meters (75 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /Flammable solid, organic, NOS (1,4-Diazabicyclo(2.2.2)octane)/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
/GUIDE 133: FLAMMABLE SOLIDS/ Protection Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Flammable solid, organic, NOS (1,4-Diazabicyclo(2.2.2)octane)/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
For more DOT Emergency Guidelines (Complete) data for 1,4-DIAZABICYCLO(2.2.2)OCTANE (8 total), please visit the HSDB record page.

11.5 Regulatory Information

The Australian Inventory of Industrial Chemicals
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
1,4-Diazabicyclo[2.2.2]octane: Does not have an individual approval but may be used under an appropriate group standard

12 Toxicity

12.1 Toxicological Information

12.1.1 Adverse Effects

Dermatotoxin - Skin burns.

12.1.2 Acute Effects

12.1.3 Human Toxicity Excerpts

/SIGNS AND SYMPTOMS/ ...Can cause corneal disturbance in workers exposed to the vapor. It is reported to have induced fine corneal epithelial edema & to have caused people to see haloes around lights several hours after exposure.
Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 1051

12.1.4 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ The acute toxicologic and pharmacologic effects of two foam catalyst amines have been determined. This work has been undertaken with the view of elucidating the possible ocular hazard which may exist after excessive inhalation of vapor in industry. By several routes of administration, tetramethylbutanediamine (TMBDA) appears to be more toxic and irritating than triethylenediamine (TED). Exposure to concentrated vapor of each amine has indicated that TMBDA will produce marked pupillary dilation and loss of accommodation after inhalation periods as short as 15 minutes, whereas a 5-hour vapor inhalation of TED is without such effects. The two amines possess marked physiological properties at intravenous doses considerably lower than those considered fatal by any route of administration. In pentobarbitalized dogs and cats, TMBDA has been shown to exhibit a selective blockade of autonomic ganglia without an accompanying effect on more peripheral sites. Ganglion blockade after TMBDA was somewhat shorter than that observed with clinically useful blocking agents. Attempts have been made to correlate these animal findings with human experiences resulting in ocular disturbances after exposure to TMBDA vapor. The pharmacologic properties of TED have been described. This agent produced in appropriate doses an initial transient depressor effect followed by a sharp and more prolonged pressor response in anesthetized animals. Depressor activity was selectively eliminated by atropine. Pressor activity was abolished by hexamethonium or tolazoline, and diminished by adrenalectomy. A partial depletion of catechol amines by reserpine caused an apparent exaggeration of pressor activity of TED. Enhancement of activity was also observed in dogs treated with dichloroisoproterenol. Adrenalectomy of dogs partially depleted of catechol amines by reserpine or a more prolonged reserpine-pretreatment stage abolished pressor response entirely while apparently augmenting the depressor activity. It was shown that TED caused a contraction of the nictitating membrane of the cat which was selectively blocked by hexamethonium. From these data, TED appears to possess two major effects, cholinomimetic and ganglion stimulating. It is concluded that the pressor activity of TED is due to sympathetic ganglion stimulation (including the adrenal medulla) which results in a release of catechol amines.
Goldberg ME, JohnsonHE; Toxicol Appl Pharmacol 4 (4) 522-45 (1962)
/OTHER TOXICITY INFORMATION/ When tested on mice the vapor /SRP: aerosol/ appears to have had no effect on the pupils or accommodation.
Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 1051

12.1.5 Non-Human Toxicity Values

LD50 Rat oral 1700 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1124
LD50 Rabbit oral 1100 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1124
LD50 Guinea pig oral 2250 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1124

12.2 Ecological Information

12.2.1 Ecotoxicity Values

LC50; Species: Pimephales promelas (Fathead minnow, size 17.5 mm, wt 0.085 g); Conditions: freshwater; flow-through; Concentration: 1730000 ug/L (95% confidence limit: 1510000 to 1980000 ug/L) for 4 days /active ingredient/
Geiger DL et al; Ctr.for Lake Superior Environ.Stud., Volume 4, Univ.of Wisconsin-Superior, Superior, WI :355 (1988) Available from, as of September 28, 2006

12.2.2 Environmental Fate / Exposure Summary

Triethylenediamine's production and use as a catalyst in the manufacture of urethane foams may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.742 mm Hg at 25 °C indicates triethylenediamine will exist solely as a vapor in the atmosphere. Vapor-phase triethylenediamine 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 18 hours. Triethylenediamine does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, triethylenediamine is expected to have very high mobility based upon an estimated Koc of 3.4. The pKa1 and pKa2 of triethylenediamine are 3.0 and 8.7, respectively, indicating that this compound will primarily exist in the cation form in the environment and cations generally have lower mobility in soils than their neutral counterparts. Volatilization from moist soil surfaces is not expected to be an important fate process since triethylenediamine primarily exists in the cation form in the environment. Triethylenediamine may volatilize from dry soil surfaces slowly based upon its vapor pressure. A 0% theoretical BOD using the Japanese MITI test suggests that biodegradation is not an important environmental fate process. If released into water, triethylenediamine is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. The pKa1 and pKa2 values of 3.0 and 8.71, respectively, indicate triethylenediamine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. Measured BCF values of <1.3 and <13 suggests 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. Occupational exposure to triethylenediamine may occur through inhalation and dermal contact with this compound at workplaces where triethylenediamine is produced or used. (SRC)

12.2.3 Artificial Pollution Sources

Triethylenediamine's production and use as a catalyst in the manufacture of urethane foams(1,2) may result in its release to the environment through various waste streams(SRC).
(1) O'Neil MJ, ed; The Merck Index. 13th ed, Whitehouse Station, NJ: Merck and Co., Inc., p. 1723 (2001)
(2) Albrecht WN, Stephenson Rl; Scand J Work Environ Health 14: 209-19 (1988)

12.2.4 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3.4(SRC), determined from a water solubility of 450 g/L(2) and a regression-derived equation(3), indicates that triethylenediamine is expected to have very high mobility in soil(SRC). The pKa1 and pKa2 of triethylenediamine are 3.0 and 8.7, respectively(2), indicating that this compound will primarily exist in cation form in the environment and cations generally have lower mobility in soils than their neutral counterparts(4). Volatilization of triethylenediamine from moist soil surfaces is not expected to be an important fate process, since this compound is expected to primarily exist in the cation form in the environment(SRC). Triethylenediamine is expected to volatilize slowly from dry soil surfaces(SRC) based upon a vapor pressure of 0.742 mm Hg(5). A 0% theoretical BOD in 4 weeks using the Japanese MITI test(6) suggests that biodegradation is not an important environmental fate process in soil(SRC).[(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) O'Neil MJ, ed; The Merck Index. 13th ed, Whitehouse Station, NJ: Merck and Co., Inc., p. 1723 (2001) (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990) (4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000) (5) Yaws CL; Handbook of Vapor Pressure. Volume 2 - C5 to C7 Compounds. Gulf Publishing Co.: Houston, TX, p. 190 (1994) (6) NITE; Chemical Risk Information Platform (CHRIP). Biodegradation and Bioconcentration. Ver 2006.01.30 Updated. National Institute of Technology and Evaluation. Tokyo, Japan. Thiodiethylene glycolbicyclo
2.2.2]octane, 1,4-diaza-. 280-57-9. Available from the database query page at https://www.safe.nite.go.jp/english/kizon/KIZON_start_hazkizon.html as of Sept 6, 2006.
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3.4(SRC), determined from a water solubility of 450 g/L(2) and a regression-derived equation(3), indicates that triethylenediamine is not expected to adsorb to suspended solids and sediment(SRC). The pKa1 and pKa2 of triethylenediamine are 3.0 and 8.7, respectively(2), which indicate triethylenediamine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), a BCF values of <1.3 and <13(5), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 0% theoretical BOD in 4 weeks using the Japanese MITI test(6) suggests that biodegradation is not an important environmental fate process in water(SRC).[(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) O'Neil MJ, ed; The Merck Index. 13th ed, Whitehouse Station, NJ: Merck and Co., Inc., p. 1723 (2001) (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) Franke C et al; Chemosphere 29: 1501-14 (1994) (5) NITE; Chemical Risk Information Platform (CHRIP). Biodegradation and Bioconcentration. Ver 2006.01.30 Updated. National Institute of Technology and Evaluation. Tokyo, Japan. Thiodiethylene glycolbicyclo
2.2.2]octane, 1,4-diaza-. 280-57-9. Available from the database query page at https://www.safe.nite.go.jp/english/kizon/KIZON_start_hazkizon.html as of Sept 6, 2006.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triethylenediamine, which has a vapor pressure of 0.742 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase triethylenediamine 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 18 hours(SRC), calculated from its rate constant of 2.2X10-11 cu cm/molecule-sec at 25 °C(3). Triethylenediamine does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Yaws CL; Handbook of Vapor Pressure. Volume 2 - C5 to C7 Compounds. Gulf Publishing Co: Houston, TX, p. 190 (1994)
(3) Koch R et al; Int J Chem Kinet 28: 807-15 (1996)
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 8-12 (1990)

12.2.5 Environmental Biodegradation

AEROBIC: Triethylenediamine, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(1).[(1) NITE; Chemical Risk Information Platform (CHRIP). Biodegradation and Bioconcentration. Ver 2006.01.30 Updated. National Institute of Technology and Evaluation. Tokyo, Japan. Thiodiethylene glycolbicyclo
2.2.2]octane, 1,4-diaza-. 280-57-9. Available from the database query page at https://www.safe.nite.go.jp/english/kizon/KIZON_start_hazkizon.html as of Sept 6, 2006.

12.2.6 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of triethylenediamine with photochemically-produced hydroxyl radicals has been reported to be 2.2X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 18 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). Triethylenediamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Triethylenediamine does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(3).
(1) Koch R et al; Int J Chem Kinet 28: 807-15 (1996)
(2) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12 (1990)

12.2.7 Environmental Bioconcentration

BCF values of <1.3 and <13 were measured using carp (Cyprinus carpio) which were exposed over an 6-week period(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).[(1) NITE; Chemical Risk Information Platform (CHRIP). Biodegradation and Bioconcentration. Ver 2006.01.30 Updated. National Institute of Technology and Evaluation. Tokyo, Japan. Thiodiethylene glycolbicyclo
2.2.2]octane, 1,4-diaza-. 280-57-9. Available from the database query page at https://www.safe.nite.go.jp/english/kizon/KIZON_start_hazkizon.html as of Sept 6, 2006. (2) Franke C et al; Chemosphere 29: 1501-14 (1994)

12.2.8 Soil Adsorption / Mobility

The Koc of triethylenediamine is estimated as 3.4(SRC), using a water solubility of 450 g/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that triethylenediamine is expected to have very high mobility in soil(SRC). The pKa1 and pKa2 values of triethylenediamine are 3.0 and 8.7(1), respectively, indicating that this compound will primarily exist in the cation form in the environment and cations generally have lower mobility in soils than their neutral counterparts(4).
(1) O'Neil MJ, ed; The Merck Index. 13th ed, Whitehouse Station, NJ: Merck and Co., Inc., p. 1723 (2001)
(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) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)

12.2.9 Volatilization from Water / Soil

Volatilization from water and moist soil surfaces is not expected to occur since triethylenediamine will exist primarily in the cation form in the environment(SRC), based on its pKa1 and pKa2 values of 3.0 and 8.7, respectively(1). Triethylenediamine is expected to volatilize slowly from dry soil surfaces(SRC) based upon a vapor pressure of 0.742 mm Hg(2).
(1) O'Neil MJ, ed; The Merck Index. 13th ed, Whitehouse Station, NJ: Merck and Co., Inc., p. 1723 (2001)
(2) Yaws CL; Handbook of Vapor Pressure. Volume 2 - C5 to C7 Compounds. Gulf Publishing Co.: Houston, TX, p. 190 (1994)

12.2.10 Probable Routes of Human Exposure

Occupational exposure to triethylenediamine may occur through inhalation and dermal contact with this compound at workplaces where triethylenediamine is produced or used(SRC). Triethylenediamine concentrations in air in a polyurethane factory ranged from 0.017 to 0.110 ppm(1).
(1) Audunsson G et al; Int J Environ Anal Chem 20: 85-100 (1985)

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Wiley References

13.6 Nature Journal References

13.7 Chemical Co-Occurrences in Literature

13.8 Chemical-Gene Co-Occurrences in Literature

13.9 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Chemical-Target Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Taxonomy

18 Classification

18.1 MeSH Tree

18.2 ChEBI Ontology

18.3 ChemIDplus

18.4 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

18.5 UN GHS Classification

18.6 EPA CPDat Classification

18.7 NORMAN Suspect List Exchange Classification

18.8 EPA DSSTox Classification

18.9 EPA TSCA and CDR Classification

18.10 EPA Substance Registry Services Tree

18.11 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
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    1,4-Diazabicyclo[2.2.2]octane
    https://www.epa.gov/chemical-data-reporting
  6. EPA Chemicals under the TSCA
    1,4-Diazabicyclo[2.2.2]octane
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  7. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
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  17. IUPHAR/BPS Guide to PHARMACOLOGY
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    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  18. Therapeutic Target Database (TTD)
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    https://haz-map.com/About
  22. NITE-CMC
    Triethylenediamine - FY2010 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/10-mhlw-0178e.html
  23. IUPAC Digitized pKa Dataset
  24. MassBank Europe
  25. NMRShiftDB
  26. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
    1,4-Diazabicyclo[2.2.2]octane
    http://www.hmdb.ca/metabolites/HMDB0244208
  27. Japan Chemical Substance Dictionary (Nikkaji)
  28. Metabolomics Workbench
  29. Natural Product Activity and Species Source (NPASS)
  30. Nature Chemistry
  31. NIST Mass Spectrometry Data Center
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  32. SpectraBase
  33. Pharos
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  44. EPA Substance Registry Services
  45. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  46. PATENTSCOPE (WIPO)
CONTENTS