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Record Information
Version1.0
Creation Date2014-09-11 05:18:58 UTC
Update Date2016-10-28 10:02:14 UTC
Accession NumberCHEM003801
Identification
Common NameDiethanolamine
ClassSmall Molecule
DescriptionDiethanolamine, often abbreviated as DEA, is an organic chemical compound which is both a secondary amine and a dialcohol. A dialcohol has two hydroxyl groups in its molecule. Like other amines, diethanolamine acts as a weak base. Diethanolamine is widely used in the preparation of diethanolamides and diethanolamine salts of long-chain fatty acids that are formulated into soaps and surfactants used in liquid laundry and dishwashing detergents, cosmetics, shampoos, and hair conditioners. Diethanolamine is also used in textile processing, in industrial gas purification to remove acid gases, as an anticorrosion agent in metalworking fluids, and in preparations of agricultural chemicals. Aqueous diethanolamine solutions are used as solvents for numerous drugs that are administered intravenously.
Contaminant Sources
  • Clean Air Act Chemicals
  • Cosmetic Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Cosmetic Toxin
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
Bis-(2-hydroxy-ethyl)-amineChEBI
DiolamineChEBI
H2dEaChEBI
N,N-Di(hydroxyethyl)amineChEBI
2,2'-DihydroxydiethylamineHMDB
2,2'-IminobisHMDB
2,2'-IminobisethanolHMDB
2,2'-Iminodi-1-ethanolHMDB
2,2'-IminodiethanolHMDB
2,2'IminobisethanolHMDB
2-(2-Hydroxyethylamino)ethanolHMDB
2-[(2-Hydroxyethyl)amino]ethanolHMDB
Aliphatic amineHMDB
Bis(2-hydroxyethyl)amineHMDB
Bis(2-hydroxyethyl)tallow amine oxideHMDB
Bis(hydroxyethyl)amineHMDB
Bis-2-hydroxyethylamineHMDB
DEAHMDB
Di(2-hydroxyethyl)amineHMDB
Di(beta-hydroxyethyl)amineHMDB
DiaethanolaminHMDB
DiethanolaminHMDB
DiethylolamineHMDB
IminodiethanolHMDB
N,N'-iminodiethanolHMDB
N,N-Bis(2-hydroxyethyl)amineHMDB
N,N-DiethanolamineHMDB
Di(β-hydroxyethyl)amineHMDB
N,N-Di(2-hydroxyethyl)amineHMDB
DiethanolamineHMDB
Chemical FormulaC4H11NO2
Average Molecular Mass105.136 g/mol
Monoisotopic Mass105.079 g/mol
CAS Registry Number111-42-2
IUPAC Name2-[(2-hydroxyethyl)amino]ethan-1-ol
Traditional Namediethanolamine
SMILESOCCNCCO
InChI IdentifierInChI=1S/C4H11NO2/c6-3-1-5-2-4-7/h5-7H,1-4H2
InChI KeyZBCBWPMODOFKDW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent1,2-aminoalcohols
Alternative Parents
Substituents
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Thyroid Gland
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point28 °C
Boiling Point268°C (514.4°F)
Solubility1000 mg/mL at 20 °C
Predicted Properties
PropertyValueSource
Water Solubility466 g/LALOGPS
logP-1.4ALOGPS
logP-1.6ChemAxon
logS0.65ALOGPS
pKa (Strongest Acidic)15.3ChemAxon
pKa (Strongest Basic)9.26ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity27.28 m³·mol⁻¹ChemAxon
Polarizability11.63 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9430000000-79f7d3e25a715793917aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001j-1900000000-bd0861145364bd684950View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0159-5940000000-ebe5523dad23d3dc2391View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-05am-9000000000-7eea9eaa21af51853910View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-9430000000-79f7d3e25a715793917aView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0159-5940000000-ebe5523dad23d3dc2391View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-001j-1900000000-bd0861145364bd684950View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS)splash10-00dj-9800000000-3db6474ab842a5d03fb3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4r-9700000000-6ae8b510d6cd7e4ba8d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0005-9000000000-d0e266aca011203c762aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0005-9000000000-b924f709a47552d0afc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0900000000-11bfee15df34ebc320e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-05g0-9200000000-39da135b20d99fa34636View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00dm-9000000000-74add71de850cb4c8e2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0005-9000000000-794a61320b2e8c5a8970View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0007-9000000000-af9eeb72884d4847a0a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-0900000000-cd466740723ff131d76fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-a5ca41984423de95ef78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05g0-9200000000-626e5d5103e3012c611eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dm-9000000000-74add71de850cb4c8e2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0005-9000000000-794a61320b2e8c5a8970View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0007-9000000000-be35c09bcc6cd8c79f05View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-cd466740723ff131d76fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0abi-9500000000-ee4dbde39d4c97f1cae9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2900000000-c1dc229350e5cf19c090View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9500000000-b3018e09980645272c12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-ae6bfcca013a433a0a24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-d6387d7e1686e32ad49aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-8900000000-66c6a6cce5f90a2cdb52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9000000000-7e1da753c608954b27eeView in MoNA
MSMass Spectrum (Electron Ionization)splash10-05fr-9000000000-362b201708dabf55f01bView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (5)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004437
FooDB IDFDB023372
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID3239
PDB IDNot Available
Wikipedia LinkDiethanolamine
Chemspider ID13835604
ChEBI ID28123
PubChem Compound ID8113
Kegg Compound IDC06772
YMDB IDNot Available
ECMDB IDECMDB21405
References
Synthesis ReferencePeschel, Werner; Hildebrandt, Axel; Bessling, Bernd. Continuous process for the synthesis of monoethanolamine, diethanolamine and triethanolamine via the addition reaction of ammonia with ethylene oxide in the presence of water as a catalyst. Eur. Pat. Appl. (2003), 11 pp.
MSDSLink
General References
1. Peschel, Werner; Hildebrandt, Axel; Bessling, Bernd. Continuous process for the synthesis of monoethanolamine, diethanolamine and triethanolamine via the addition reaction of ammonia with ethylene oxide in the presence of water as a catalyst. Eur. Pat. Appl. (2003), 11 pp.
2. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.
3. Peschel, Werner; Hildebrandt, Axel; Bessling, Bernd. Continuous process for the synthesis of monoethanolamine, diethanolamine and triethanolamine via the addition reaction of ammonia with ethylene oxide in the presence of water as a catalyst. Eur. Pat. Appl. (2003), 11 pp.
4. Mathews JM, deCosta K, Thomas BF: Lauramide diethanolamine absorption, metabolism, and disposition in rats and mice after oral, intravenous, and dermal administration. Drug Metab Dispos. 1996 Jul;24(7):702-10.
5. Zeisel SH, DaCosta KA, Fox JG: Endogenous formation of dimethylamine. Biochem J. 1985 Dec 1;232(2):403-8.
6. Authors unspecified: NTP Toxicology and Carcinogenesis Studies of Lauric Acid Diethanolamine Condensate (CAS NO. 120-40-1) in F344/N Rats and B6C3F1 Mice (Dermal Studies). Natl Toxicol Program Tech Rep Ser. 1999 Jul;480:1-200.
7. Authors unspecified: NTP Toxicology and Carcinogenesis Studies of Diethanolamine (CAS No. 111-42-2) in F344/N Rats and B6C3F1 Mice (Dermal Studies). Natl Toxicol Program Tech Rep Ser. 1999 Jul;478:1-212.
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=12571685
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15304302
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23567043
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24275050