Diethanolamine (CHEM003801)

Record Information
Version1.0
Creation Date2014-09-11 05:18:58 UTC
Update Date2026-08-22 15:37:26 UTC
Accession NumberCHEM003801
Identification
Common NameDiethanolamine
ClassSmall Molecule
Description
Diethanolamine, 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
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
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
DiethanolamineHMDB
N,N-Di(2-hydroxyethyl)amineHMDB
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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
External Links
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. https://www.ncbi.nlm.nih.gov/pubmed/?term=12571685
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15304302
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23567043
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24275050
5. 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.
6. 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.
7. 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.
8. 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.
9. Zeisel SH, DaCosta KA, Fox JG: Endogenous formation of dimethylamine. Biochem J. 1985 Dec 1;232(2):403-8.
10. 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.
11. 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.