Ethanolamine

Ethanolamine
Names
	Preferred IUPAC name 2-Aminoethan-1-ol
	Other names 2-Aminoethanol; 2-Amino-1-ethanol; Ethanolamine (not recommended); Monoethanolamine; β-Aminoethanol; β-hydroxyethylamine; β-Aminoethyl alcohol; Glycinol; Olamine; MEA; Ethylolamine; 2-Hydroxyethylamine; Colamine;
Identifiers
CAS Number	141-43-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16000 ;
ChEMBL	ChEMBL104943 ;
ChemSpider	13835336 ;
DrugBank	DB03994 ;
ECHA InfoCard	100.004.986
EC Number	205-483-3;
KEGG	D05074 ;
PubChem CID	700;
RTECS number	KJ5775000;
UNII	5KV86114PT ;
CompTox Dashboard (EPA)	DTXSID6022000 ;
	InChI InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2 Key: HZAXFHJVJLSVMW-UHFFFAOYSA-N ; InChI=1/C2H7NO/c3-1-2-4/h4H,1-3H2 Key: HZAXFHJVJLSVMW-UHFFFAOYAD;
	SMILES NCCO;
Properties
Chemical formula	C2H7NO
Molar mass	61.084 g·mol−1
Appearance	Viscous colourless liquid
Odor	Unpleasant ammonia-like odour
Density	1.0117 g/cm3
Melting point	10.3 °C (50.5 °F; 283.4 K)
Boiling point	170 °C (338 °F; 443 K)
Solubility in water	Miscible
Vapor pressure	64 Pa (20 °C)
Acidity (pKa)	9.50
Refractive index (nD)	1.4539 (20 °C)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H312, H314, H332, H335, H412
Precautionary statements	P261, P273, P303+P361+P353, P305+P351+P338
NFPA 704 (fire diamond)	3 2 0
Flash point	85 °C (185 °F; 358 K) (closed cup)
Autoignition; temperature	410 °C (770 °F; 683 K)
Explosive limits	5.5–17%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	3320 mg/kg (rat, oral); 620 mg/kg (guinea pig, oral); 2050 mg/kg (rat, oral); 1475 mg/kg (mouse, oral); 1000 mg/kg (rabbit, oral); 700 mg/kg (mouse, oral); 1720–1970 mg/kg (rat, oral);
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA: 3 ppm (6 mg/m3)
REL (Recommended)	TWA: 3 ppm (8 mg/m3); ST: 6 ppm (15 mg/m3);
IDLH (Immediate danger)	30 ppm
Safety data sheet (SDS)	Sigma
Related compounds
Related compounds	N-Methylethanolamine; Diethanolamine; Triethanolamine;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is a naturally occurring organic chemical compound with the formula HOCH
₂CH
₂NH
₂ or C
₂H
₇NO.^[8] The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid with an odor reminiscent of ammonia.^[9]

Ethanolamine is commonly called monoethanolamine or MEA in order to be distinguished from diethanolamine (DEA) and triethanolamine (TEA). The ethanolamines comprise a group of amino alcohols. A class of antihistamines is identified as ethanolamines, which includes carbinoxamine, clemastine, dimenhydrinate, chlorphenoxamine, diphenhydramine and doxylamine.^[10]

^ ^a ^b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 649, 717. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. For example, the name 'ethanolamine', which is still widely used, is badly constructed because of the presence of two suffixes; it is not an alternative to the preferred IUPAC name, '2-aminoethan-1-ol'.
^ "Ethanolamine MSDS" (PDF). Acros Organics. Archived from the original (PDF) on 2011-07-15.
^ Hall, H.K. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441–4. doi:10.1021/ja01577a030.
^ Reitmeier, R.E.; Sivertz, V.; Tartar, H.V. (1940). "Some Properties of Monoethanolamine and its Aqueous Solutions". Journal of the American Chemical Society. 62 (8): 1943–44. doi:10.1021/ja01865a009.
^ ^a ^b ^c Sigma-Aldrich Co., Ethanolamine. Retrieved on 2018-05-24.
^ ^a ^b ^c NIOSH Pocket Guide to Chemical Hazards. "#0256". National Institute for Occupational Safety and Health (NIOSH).
^ "Ethanolamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ "National Library of Medicine. PubChem. Ethanolomine". NIH, National Library of Medicine. Retrieved September 5, 2021.
^ Martin Ernst; Johann-Peter Melder; Franz Ingo Berger; Christian Koch (2022). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001.pub2. ISBN 978-3527306732.
^ Cough, Cold, and Allergy Preparation Toxicity at eMedicine

[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 649, 717. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. For example, the name 'ethanolamine', which is still widely used, is badly constructed because of the presence of two suffixes; it is not an alternative to the preferred IUPAC name, '2-aminoethan-1-ol'.

[2] "Ethanolamine MSDS" (PDF). Acros Organics. Archived from the original (PDF) on 2011-07-15.

[3] Hall, H.K. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441–4. doi:10.1021/ja01577a030.

[4] Reitmeier, R.E.; Sivertz, V.; Tartar, H.V. (1940). "Some Properties of Monoethanolamine and its Aqueous Solutions". Journal of the American Chemical Society. 62 (8): 1943–44. doi:10.1021/ja01865a009.

[sigma-5] Sigma-Aldrich Co., Ethanolamine. Retrieved on 2018-05-24.

[NIOSH-6] NIOSH Pocket Guide to Chemical Hazards. "#0256". National Institute for Occupational Safety and Health (NIOSH).

[7] "Ethanolamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[8] "National Library of Medicine. PubChem. Ethanolomine". NIH, National Library of Medicine. Retrieved September 5, 2021.

[Ullmann-9] Martin Ernst; Johann-Peter Melder; Franz Ingo Berger; Christian Koch (2022). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001.pub2. ISBN 978-3527306732.

[10] Cough, Cold, and Allergy Preparation Toxicity at eMedicine

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Names


Preferred IUPAC name 2-Aminoethan-1-ol^[1]
Other names 2-Aminoethanol 2-Amino-1-ethanol Ethanolamine (not recommended^[1]) Monoethanolamine β-Aminoethanol β-hydroxyethylamine β-Aminoethyl alcohol Glycinol Olamine MEA Ethylolamine 2-Hydroxyethylamine Colamine
Identifiers
CAS Number	141-43-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16000^Y
ChEMBL	ChEMBL104943^Y
ChemSpider	13835336^Y
DrugBank	DB03994^Y
ECHA InfoCard	100.004.986
EC Number	205-483-3
KEGG	D05074^Y
PubChem CID	700
RTECS number	KJ5775000
UNII	5KV86114PT^Y
CompTox Dashboard (EPA)	DTXSID6022000
InChI InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2^Y Key: HZAXFHJVJLSVMW-UHFFFAOYSA-N^Y InChI=1/C2H7NO/c3-1-2-4/h4H,1-3H2 Key: HZAXFHJVJLSVMW-UHFFFAOYAD
SMILES NCCO
Properties
Chemical formula	C₂H₇NO
Molar mass	61.084 g·mol⁻¹
Appearance	Viscous colourless liquid
Odor	Unpleasant ammonia-like odour
Density	1.0117 g/cm³
Melting point	10.3 °C (50.5 °F; 283.4 K)
Boiling point	170 °C (338 °F; 443 K)
Solubility in water	Miscible
Vapor pressure	64 Pa (20 °C)^[2]
Acidity (pK_a)	9.50^[3]
Refractive index (n_D)	1.4539 (20 °C)^[4]
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H312, H314, H332, H335, H412^[5]
Precautionary statements	P261, P273, P303+P361+P353, P305+P351+P338^[5]
NFPA 704 (fire diamond)	3 2 0
Flash point	85 °C (185 °F; 358 K) (closed cup)
Autoignition temperature	410 °C (770 °F; 683 K)
Explosive limits	5.5–17%
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	3320 mg/kg (rat, oral) 620 mg/kg (guinea pig, oral) 2050 mg/kg (rat, oral) 1475 mg/kg (mouse, oral) 1000 mg/kg (rabbit, oral) 700 mg/kg (mouse, oral) 1720–1970 mg/kg (rat, oral)^[7]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA: 3 ppm (6 mg/m³)^[6]
REL (Recommended)	TWA: 3 ppm (8 mg/m³) ST: 6 ppm (15 mg/m³)^[6]
IDLH (Immediate danger)	30 ppm^[6]
Safety data sheet (SDS)	Sigma^[5]
Related compounds
Related compounds	N-Methylethanolamine Diethanolamine Triethanolamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references