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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
Assay:
94%
Form:
liquid

Key Documents

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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

Quality Level

200

bp

102-103 °C/720 mmHg (lit.)

density

0.897 g/mL at 25 °C (lit.)

functional group

amine, ether

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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.
C Rodier et al.
Chirality, 14(6), 527-532 (2002-07-12)
Two different methods of derivatization were studied in order to select and optimize one for the in situ enantiomeric separation of amino acids present in Martian samples. The method, using DMF-DMA [N,N-dimethylformamide dimethyl acetal], is simple and easily automated. However
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