N,N-Dimethylformamide diethyl acetal

Name: <I>N</I>,<I>N</I>-Dimethylformamide diethyl acetal
Brand: SIAL

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

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

329755961

EC Number:

214-707-9

Beilstein/REAXYS Number:

741889

MDL number:

MFCD00009227

Assay:

≥95.0% (GC)

Key Documents

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InChI key

BWKAYBPLDRWMCJ-UHFFFAOYSA-N

InChI

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

SMILES string

CCOC(OCC)N(C)C

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.)

functional group

amine, ether

Quality Level

100

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Show Differences

1 of 4

This Item	142778	PHR3318	1273841
Sigma-Aldrich 40252 N,N-Dimethylformamide diethyl acetal	Sigma-Aldrich 142778 N,N-Dimethylformamide diethyl acetal	Supelco PHR3318 Flumazenil Related Compound C	USP 1273841 Flumazenil Related Compound C
assay ≥95.0% (GC)	assay 95%	assay -	assay -
Quality Level 100	Quality Level 100	Quality Level 300	Quality Level -
bp 130-133 °C (lit.)	bp 130-133 °C (lit.)	bp 130-133 °C (lit.)	bp 130-133 °C (lit.)
density 0.859 g/mL at 25 °C (lit.)	density 0.859 g/mL at 25 °C (lit.)	density 0.859 g/mL at 25 °C (lit.)	density 0.859 g/mL at 25 °C (lit.)
refractive index n20/D 1.397-1.401	refractive index n20/D 1.400 (lit.)	refractive index n20/D 1.400 (lit.)	refractive index n20/D 1.400 (lit.)
quality for esterification of fatty acids	quality -	quality -	quality -

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.[1]

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.[2]

N,N-Dimethylformamide diethyl acetal (DMF diethyl acetal) on reaction with butanol affords N,N-dimethylformamide dibutyl acetal.[3] It participates in various alkylation, formylation, and aminomethylenation reactions. It has been synthesized from N,N-dialkyl(chloromethylene)ammonium chloride.[4]

Other Notes

Reagent for the esterification of fatty acids[5]; Review[6]

pictograms

GHS02

signalword

Warning

hcodes

H226

pcodes

P210 - P370 + P378

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

82.4 °F - closed cup

flash_point_c

28 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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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)

Me3SiCl-promoted three-component coupling reaction of a functionalized enamine, an acetal, and an alkyne: an unprecedented approach to the synthesis of tetrasubstituted pyridines via a [3 + 2 + 1] intermolecular cyclization.

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.

Simultaneous determination of cocaine and benzoyl ecgonine in urine by gas chromatography with on-column alkylation.

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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