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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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.
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)
Qingfen Zhang et al.
Journal of the American Society for Mass Spectrometry, 16(7), 1192-1203 (2005-06-01)
A fragmentation mechanism for the neutral loss of 73 Da from dimethylformamidine glutamine isobutyl ester is investigated. Understanding this mechanism will allow to improve the identification and quantification of 15N-labeled and unlabeled glutamine and the distinguishing of glutamine and glutamic
Anirban Sarkar et al.
Organic & biomolecular chemistry, 10(2), 281-286 (2011-11-08)
1-Methylimidazole exhibits an unusually high efficiency in promoting the reaction of aryl methyl ketones with DMF-DMA to form (2E)-1-aryl-3-dimethylamino-2-propenones which lacks correlation between the catalytic efficiency and the basicity of 1-methylimidazole in comparison to other amines. An unprecedented supramolecular domino
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