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Merck
CN

140732

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
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
24848474
EC Number:
225-063-3
Beilstein/REAXYS Number:
506020
MDL number:
MFCD00008482

Key Documents

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Product Name

N,N-Dimethylformamide dimethyl acetal, technical grade, 94%

InChI key

ZSXGLVDWWRXATF-UHFFFAOYSA-N

InChI

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

SMILES string

COC(OC)N(C)C

grade

technical grade

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.)

functional group

amine
ether

Quality Level

200

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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.

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Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

42.8 °F

flash_point_c

6 °C

ppe

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCX5498
MKBX5603V
MKBV2100V
MKBL2739V
MKBK5062V

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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.
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.
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