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140732

Sigma-Aldrich

N,N-Dimethylformamide dimethyl acetal

technical grade, 94%

Synonym(s):

1,1-Dimethoxy-N,N-dimethylmethylamine, 1,1-Dimethoxytrimethylamine

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About This Item

Linear Formula:
(CH3)2NCH(OCH3)2
CAS Number:
4637-24-5
Molecular Weight:
119.16
Beilstein:
506020
EC Number:
225-063-3
MDL number:
MFCD00008482
UNSPSC Code:
12352302
PubChem Substance ID:
24848474
NACRES:
NA.22

grade

technical grade

Quality Level

200

Assay

94%

form

liquid

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.396 (lit.)

bp

102-103 °C/720 mmHg (lit.)

density

0.897 g/mL at 25 °C (lit.)

SMILES string

COC(OC)N(C)C

InChI

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

InChI key

ZSXGLVDWWRXATF-UHFFFAOYSA-N

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Application

N,N-Dimethylformamide dimethyl acetal (DMF-DMA) can be used as: 
  • An organocatalyst for the synthesis of 1,2-disubstituted-3,4-dihydronaphthalenes by the reaction of vinylarenes and electron-deficient alkynes.       
  • A building block for the preparation of heterocyclic compounds such as enamines and amidines via formylation of methylene and amino groups.       
  • A reagent in the synthesis of 1,4-diaryl-piperazine-2,5-diones by reacting with chloroacetamides.        
  • A reagent along with enamine and alkyne for the preparation of 2,3,4,5-tetrasubstituted pyridine derivatives by three-component coupling reaction in the presence of Me3SiCl.

Signal Word

Danger

Hazard Statements

H225,H317,H318,H332

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

42.8 °F

Flash Point(C)

6 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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A highly efficient cycloaddition of vinylarenes with electron-deficient alkynes affording 1, 2-disubstituted-3, 4-dihydronaphthalenes catalysed by N, N-dimethylformamide dimethyl acetal
Jiang J-L, et al.
Organic & Biomolecular Chemistry, 5(12), 1854-1857 (2007)
Synthesis of 1, 4-Diaryl-piperazine-2, 5-diones: New Behavior of N, N-Dimethylformamide Dimethyl Acetal (DMFDMA)
Abu-Shanab FA, et al.
Synthetic Communications, 38(3), 376-382 (2008)
Dimethylformamide dimethyl acetal as a building block in heterocyclic synthesis
Abu-Shanab FA, et al.
Journal of Heterocyclic Chemistry, 46(5), 801-827 (2009)
Wim Schepens et al.
Organic letters, 8(19), 4247-4250 (2006-09-08)
A novel series of analogues of calcitriol (1) is developed featuring a spirocyclic central core resulting from C18/C21-connection and C15/C16-deletion (2a, 2b). The synthesis of the key intermediate involves an Eschenmoser rearrangement of an enantiomerically pure bromo-substituted cyclohexenol.
M F Grubb et al.
Journal of chromatography, 469, 191-196 (1989-05-19)
Six amino acids containing either an N-methyl or a cyclic secondary amine were converted to volatile derivatives by reaction with dimethylformamide dimethyl acetal. The amine functionalities were formylated by way of an amide acetal intermediate while the carboxylic acid groups
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