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391263

Sigma-Aldrich

2-Dimethylaminoethanol

purified by redistillation, ≥99.5%

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Synonym(s):
N,N-Dimethyl-2-hydroxyethylamine, N,N-Dimethylethanolamine, Jeffcat DMEA
Linear Formula:
(CH3)2NCH2CH2OH
CAS Number:
108-01-0
Molecular Weight:
89.14
Beilstein:
1209235
EC Number:
203-542-8
MDL number:
MFCD00002846
UNSPSC Code:
12352100
PubChem Substance ID:
24864369
NACRES:
NA.22

vapor pressure

100 mmHg ( 55 °C)
6.12 mmHg ( 20 °C)

Quality Level

100

Assay

≥99.5%

form

liquid

purified by

redistillation

refractive index

n20/D 1.4294 (lit.)

bp

134-136 °C (lit.)

mp

−70 °C (lit.)

solubility

alcohol: miscible(lit.)
water: soluble

density

0.886 g/mL at 20 °C (lit.)

SMILES string

CN(C)CCO

InChI

1S/C4H11NO/c1-5(2)3-4-6/h6H,3-4H2,1-2H3

InChI key

UEEJHVSXFDXPFK-UHFFFAOYSA-N

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General description

2-Dimethylaminoethanol (DMAE/deanol) is an amino alcohol. It is the main product formed during the amination of ethylene glycol by dimethylamine on alumina supported copper in a continuous fixed-bed reactor. DMAE has been reported to be the putative precursor of acetylcholine. Its effect as a skin-firming and anti-wrinkle agent has been studied. Microwave spectrum of 2-dimethylaminoethanol has been investigated. Its effect as an organic additive on deposition and anti-reflective properties of porous CaF2 has been studied. Removal of the benzyl ester groups by transesterification with 2-dimethylaminoethanol from benzyl protected tripeptides has been reported.

Application

2-Dimethylaminoethanol (deanol) may be used as a ligand in the copper-catalyzed amination of aryl bromides and iodides.
2-Dimethylaminoethanol (deanol, DMAE, DMEA) may be used in the synthesis of the following:
  • cis -[Co(sac)2(dmea)2] and cis -[Zn(sac)2(dmea)2] (sac=saccharinate)
  • heterotrinuclear complex [Cu2Zn(NH3)I3(Me2Ea)3 (HMe2Ea=2-dimethylaminoethanol)
  • 2-alkoxy-N,N-dimethylethylamine
  • mixed-metal complexes of copper(II) and lead(II)

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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An incomplete cube-like array of Cu, Zn, I with O atoms from 2-dimethylaminoethanol formed directly from zero-valent metal powders.
Vinogradova EA, et al.
Inorganic Chemistry Communications, 5(1), 19-22 (2002)
cis-bis (Saccharinato) cobalt (II) and-zinc (II) complexes with 2-dimethylaminoethanol: syntheses, crystal structures, spectroscopic and thermal studies.
Yilmaz VT, et al.
Journal of Coordination Chemistry, 59(17), 1937-1944 (2006)
Synthesis and properties of 2-alkoxy-N,N-dimethylethylamine N-oxides.
Hayashi Y, et al
Journal of the American Oil Chemists' Society, 62(3), 555-557 (1985)
Copper-catalyzed aryl amination in aqueous media with 2-dimethylaminoethanol ligand.
Lu Z and Twieg RJ.
Tetrahedron Letters, 47(17), 2997-3001 (2005)
L E Larsson et al.
International journal of peptide and protein research, 8(1), 39-44 (1976-01-01)
A convenient scheme for the synthesis of 4,8-disubstituted vasopressins has been designed and its usefulness evaluated in the preparation of one of the parent hormones, 8-arginine-vasopressin. The main feature of the scheme involves preparation of two protected tripeptide fragments, Z-Cys(Bzl)-Tyr(Bzl)-Phe
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