Dimethylethanolamine

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Dimethylethanolamine
Skeletal formula of dimethylethanolamine
Ball-and-stick model of the dimethylethanolamine molecule
Names
IUPAC name
2-(Dimethylamino)ethanol
Other names
deanol, dimethylaminoethanol, dimethylaminoethanol
Identifiers
3D model (JSmol)
Abbreviations DMAE, DMEA
1209235
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.221
EC Number 203-542-8
KEGG
MeSH Deanol
RTECS number KK6125000
UNII
UN number 2051
Properties
C4H11NO
Molar mass 89.14 g·mol−1
Appearance Colourless liquid
Odor Fishy, ammoniacal
Density 890 mg mL−1
Melting point −59.00 °C; −74.20 °F; 214.15 K
Boiling point 134.1 °C; 273.3 °F; 407.2 K
log P −0.25
Vapor pressure 816 Pa (at 20 °C)
Acidity (pKa) 9.23 (at 20 °C)[1]
Basicity (pKb) 4.77 (at 20 °C)
1.4294
Pharmacology
N06BX04 (WHO)
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H226, H302, H312, H314, H332
P280, P305+351+338, P310
Flash point 39 °C (102 °F; 312 K)
Explosive limits 1.4–12.2%
Lethal dose or concentration (LD, LC):
  • 1.214 g kg−1 (dermal, rabbit)
  • 2 g kg−1 (oral, rat)
Related compounds
Related alkanols
Related compounds
Diethylhydroxylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dimethylethanolamine (DMAE or DMEA) is an organic compound with the formula (CH3)2NCH2CH2OH. It is bifunctional, containing both a tertiary amine and primary alcohol functional groups. It is a colorless viscous liquid. It is used in skin care products. It is prepared by the ethoxylation of dimethylamine.[2]

Industrial uses[edit]

It is a precursor to other chemicals, such as the nitrogen mustard 2-dimethylaminoethyl chloride.[3] The acrylate ester is used as a flocculating agent.

Related compounds are used in gas purification, e.g. removal of hydrogen sulfide from sour gas streams.

Neutraceutical uses[edit]

The bitartrate salt of DMAE, i.e. 2-dimethylaminoethanol (+)-bitartrate, is sold as a dietary supplement.[4] It is a white powder providing 37% DMAE.[5]

See also[edit]

References[edit]

  1. ^ Littel, RJ; Bos, M; Knoop, GJ (1990). "Dissociation constants of some alkanolamines at 293, 303, 318, and 333 K" (Submitted manuscript). Journal of Chemical and Engineering Data. 35 (3): 276–77. doi:10.1021/je00061a014. INIST:19352048.
  2. ^ Matthias Frauenkron, Johann-Peter Melder, Günther Ruider, Roland Rossbacher, Hartmut Höke (2002). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001.
  3. ^ Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, ISBN 978-0-9522674-3-0, p. 3294.
  4. ^ Karen E. Haneke & Scott Masten, 2002, "Dimethylethanolamine (DMAE) [108-01-0] and Selected Salts and Esters: Review of Toxicological Literature (Update)," Report on National Institute of Environmental Health Sciences Contract No. N01-ES-65402, November 2002, from Contractee Integrated Laboratory Systems, Research Triangle Park, North Carolina 27709, see [1], accessed 30 April 2015.
  5. ^ Sigma Aldrich: Safety Data Sheet: 2-Dimethylaminoethanol (+)-bitartrate