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8.03068

Sigma-Aldrich

N,N-Dimethylformamide dimethyl acetal

for synthesis

Sinónimos:

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

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About This Item

Fórmula lineal:
(CH3O)2CHN(CH3)2
Número de CAS:
4637-24-5
Peso molecular:
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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
DMFDMA catalyzed synthesis of 2-((Dimethylamino) methylene)-3, 4-dihydro-9-arylacridin-1 (2H)-ones and their derivatives: in-vitro antifungal, antibacterial and antioxidant evaluations
Kumar L, et al.
open chemistry, 16(1), 1077-1088 (2018)
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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