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40252

Sigma-Aldrich

N,N-Dimethylformamide diethyl acetal

for esterification of fatty acids, ≥95.0% (GC)

Synonym(s):

1,1-Diethoxy-N,N-dimethylmethylamine, 1,1-Diethoxytrimethylamine

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About This Item

Linear Formula:
(CH3)2NCH(OC2H5)2
CAS Number:
1188-33-6
Molecular Weight:
147.22
Beilstein:
741889
EC Number:
214-707-9
MDL number:
MFCD00009227
UNSPSC Code:
12352100
PubChem Substance ID:
329755961
NACRES:
NA.22

Quality Level

100

Assay

≥95.0% (GC)

quality

for esterification of fatty acids

color

colorless to yellow

refractive index

n20/D 1.397-1.401
n20/D 1.400 (lit.)

bp

130-133 °C (lit.)

density

0.859 g/mL at 25 °C (lit.)

SMILES string

CCOC(OCC)N(C)C

InChI

1S/C7H17NO2/c1-5-9-7(8(3)4)10-6-2/h7H,5-6H2,1-4H3

InChI key

BWKAYBPLDRWMCJ-UHFFFAOYSA-N

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General description

N,N-Dimethylformamide diethyl acetal undergoes Me3SiCl-mediated three-component coupling reaction with alkyne to yield 2,3,4,5-tetrasubstituted pyridine derivatives.
N,N-Dimethylformamide diethyl acetal (DMF diethyl acetal) on reaction with butanol affords N,N-dimethylformamide dibutyl acetal. It participates in various alkylation, formylation, and aminomethylenation reactions. It has been synthesized from N,N-dialkyl(chloromethylene)ammonium chloride.

Application

N,N-Dimethylformamide diethyl acetal is a suitable reagent for the esterification of fatty acids. It is suitable reagent used in the quantification of cocaine and its primary metabolite, benzoyl ecgonine, from a urine matrix by gas chromatography.

Other Notes

Reagent for the esterification of fatty acids; Review

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Precautionary Statements

P210 - P370 + P378

Hazard Classifications

Flam. Liq. 3

WGK

WGK 3

Flash Point(F)

82.4 °F

Flash Point(C)

28 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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N,N-Dimethylformamide Diethyl Acetal.
Pindur U.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2001)
J.P. Thenot et al.
Analytical Letters, 217-217 (1972)
DeWolfe RH.
Carboxylic Ortho Acid Derivatives: Preparation and Synthetic Applications (Academic press), 14, 424-424 (2012)
Toshiaki Sasada et al.
The Journal of organic chemistry, 73(17), 6905-6908 (2008-07-30)
We have identified a Me3SiCl-mediated three-component coupling reaction of a functionalized enamine, N,N-dimethylformamide diethyl acetal, and an internal alkyne having an electron-withdrawing group that produces 2,3,4,5-tetrasubstituted pyridine derivatives in good to excellent yields via a single-step reaction.
N C Jain et al.
Journal of forensic sciences, 22(1), 7-16 (1977-01-01)
A gas chromatographic procedure has been developed for the simultaneous determination of cocaine and benzoyl ecgonine in urine specimens. The two drugs are extracted by isopropanol/chloroform from urine samples saturated with a bisalt buffer. The organic extract is evaporated to
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