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DMF

(Dimethylformamide)


Other Names:

N,N-Dimethylformamide






General Information:


Structure:



CAS Number: 68-12-2

Molecular Weight: 73.09 g/mol

Appearance: Colorless liquid

Melting Point: -61 C

Boiling Point: 153 C

Density: 0.944 g/mL


Dimethylformamide (DMF) is a polar aprotic solvent with a high boiling point (153 C). DMF is also used as a reagent in some reactions. A closely related solvent is dimethylacetamide (DMA).




Common Uses:


Catalytic reagent used with oxalyl chloride to convert carboxylic acids to acid chlorides





Reagent used for formylation reactions




Solvent for reactions





Safety:


Reactions using NaH in DMF can have sudden exotherms. This can be dangerous, especially on large scale. Runaway reactions have taken place between NaH and DMF. Under acidic or basic conditions, DMF is known to disproportionate to carbon monoxide and dimethylamine.




References:


1) WO2016011390, page 126

2) WO2015088045, page 146

3) WO2016014463, page 93

4) WO2014149164, page 261

5) Wikipedia: Dimethylformamide (link)

6) www.sigmaaldrich.com: N,N-Dimethylformamide (link)

7) Anderson, N. G.; Practical Process Research and Development, a Guide for Organic Chemists, 2nd Edition