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Dimethylformamide, DMF is an organic compound with the chemical formula H C O N(CH 3) 2. Its structure is HC(=O)−N( −CH 3 ) 2 . Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran , or dimethyl fumarate ), this colourless liquid is miscible with water and the majority of organic liquids.
For instance, dimethylformamide ((CH 3) 2 NC(O)H) slowly decomposes to give dimethylamine and carbon monoxide when heated to its boiling point (154 °C). Some derivatives of formic acid, like formyl chloride ( −COCl ), undergo spontaneous decarbonylation at room temperature (or below).
N,N-dimethylformamide + H 2 O dimethylamine + formate Thus, the two substrates of this enzyme are N,N-dimethylformamide and H 2 O , whereas its two products are dimethylamine and formate . This enzyme belongs to the family of hydrolases , those acting on carbon-nitrogen bonds other than peptide bonds, specifically in linear amides.
Formyl functional group is shown in blue. Formylation refers to any chemical processes in which a compound is functionalized with a formyl group (-CH=O). In organic chemistry, the term is most commonly used with regards to aromatic compounds (for example the conversion of benzene to benzaldehyde in the Gattermann–Koch reaction).
Vilsmeier reagent is the active intermediate in the formylation reactions, the Vilsmeier reaction or Vilsmeier-Haack reaction that use mixtures of dimethylformamide and phosphorus oxychloride to generate the Vilsmeier reagent, which in turn attacks a nucleophilic substrate and eventually hydrolyzes to give formyl.
The Vilsmeier–Haack reaction (also called the Vilsmeier reaction) is the chemical reaction of a substituted formamide (1) with phosphorus oxychloride and an electron-rich arene (3) to produce an aryl aldehyde or ketone (5):
The first step is the formation of an enamine 2 using N,N-dimethylformamide dimethyl acetal and pyrrolidine. The desired indole 3 is then formed in a second step by reductive cyclisation. The Leimgruber-Batcho indole synthesis. In the above scheme, the reductive cyclisation is effected by Raney nickel and hydrazine.
N-Methylformamide (NMF) is a colorless, nearly odorless, organic compound and secondary amide with molecular formula CH 3 NHCHO, which is a liquid at room temperature. NMF is mainly used as a reagent in various organic syntheses with limited applications as a highly polar solvent.