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Key Documents

8.03068

Sigma-Aldrich

N,N-Dimethylformamide dimethyl acetal

for synthesis

Synonym(s):

N,N-Dimethylformamide dimethyl acetal, N,N-Dimethyldimethoxymethylamine, DMF-DMA

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About This Item

Linear Formula:
(CH3O)2CHN(CH3)2
CAS Number:
4637-24-5
Molecular Weight:
119.16
MDL number:
MFCD00008482
UNSPSC Code:
12352116
EC Index Number:
225-063-3
NACRES:
NA.22

Quality Level

200

form

liquid

autoignition temp.

155 °C

potency

>5000 mg/kg LD50, oral (Rat)

expl. lim.

1.3-17.7 % (v/v)

pH

7 ( in H2O)

mp

-85 °C

transition temp

flash point 6 °C

density

0.895 g/cm3 at 20 °C

storage temp.

2-30°C

InChI

1S/C5H13NO2/c1-6(2)5(7-3)8-4/h5H,1-4H3/p+1

InChI key

ZSXGLVDWWRXATF-UHFFFAOYSA-O

General description

N, N-Dimethylformamide dimethyl acetal (DMF-DMA) plays an important role in organic synthesis due to its higher reactivity.

  • As a methylating agent, DMF-DMA has been used in the synthesis of methyl esters from acids, methyl ethers, and thioethers from phenols and aromatic thiols.
  • DMF-DMA has been used as a formulating agent to synthesize enamines from active methylenes and active methyl groups, and amidines from amines and amides or thioamide.
  • It is also possible to produce heterocyclic compounds using DMF-DMA by cyclizing two functional groups.

Application

N,N-Dimethylformamide dimethyl acetal is used:

  • In the synthesis of spirooxindole and pyrazole scaffolds via [3+2] cycloaddition reaction of electron-deficient olefins-based pyrazole motif.
  • As a reagent in the synthesis of3-acetyl-4-arylquinoline-based enaminones under microwave irradiation.

Analysis Note

Assay (HClO₄): ≥ 96.0 %
Density (d 20 °C/ 4 °C): 0.893 - 0.897
Identity (IR): passes test

signalword

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Eye Dam. 1 - Flam. Liq. 2 - Repr. 1B - Skin Sens. 1

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

42.8 °F

flash_point_c

6 °C

Certificates of Analysis (COA)

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Dimethylformamide dimethyl acetal as a building block in heterocyclic synthesis
Abu-Shanab FA, et al.
Journal of Heterocyclic Chemistry, 46(5), 801-827 (2009)
Regio-and stereoselective synthesis of spiro-heterocycles bearing the pyrazole scaffold via [3+ 2] cycloaddition reaction
Journal of Molecular Structure, 1250, 131711-131711 (2022)

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