''N''-Methylformamide (NMF) is a colorless, nearly odorless,

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

and

secondary amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is p ...

with molecular formula CH₃NHCHO, 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 A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for p ...

. NMF is closely related to other formamides, notably

formamide Formamide is an amide derived from formic acid. It is a colorless liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs and other pharmaceuticals, herbicides and pesticide ...

and

dimethylformamide Dimethylformamide is an organic compound with the formula ( CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majo ...

(DMF). However, industrial use and production of NMF are far less than for either of these other formamides. DMF is favored over NMF as a

solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

due to its greater stability. Annual production of NMF can be assumed to be significantly less than the production of either formamide (100,000 tons) or DMF (500,000 tons).

Structure and properties

Like DMF and formamide, each of the two

rotamer In chemistry, conformational isomerism is a form of stereoisomerism in which the isomers can be interconverted just by rotations about formally single bonds (refer to figure on single bond rotation). While any two arrangements of atoms in a molec ...

s of NMF are described by two principal

resonance structure In chemistry, resonance, also called mesomerism, is a way of describing Chemical bond, bonding in certain molecules or polyatomic ions by the combination of several contributing structures (or ''forms'', also variously known as ''resonance stru ...

s: :: This description highlights the partial double bond that exists between the carbonyl carbon and nitrogen, which gives rise to a high rotational barrier. Thus, the molecule is not able to freely rotate around its main axis and the (''E'')-configuration is preferred due to steric repulsion of the larger substituents. This molecule has been tentatively identified in interstellar space by the

ALMA Alma or ALMA may refer to: Arts and entertainment * ''Alma'' (film), a 2009 Spanish short animated film * ''Alma'' (Oswald de Andrade novel), 1922 * ''Alma'' (Le Clézio novel), 2017 * ''Alma'' (play), a 1996 drama by Joshua Sobol about Alma ...

radio telescope. It may have formed on dust grains. This could prove to be a key molecule for interstellar pre-biotic chemistry due to its

peptide bond In organic chemistry, a peptide bond is an amide type of covalent chemical bond linking two consecutive alpha-amino acids from C1 (carbon number one) of one alpha-amino acid and N2 (nitrogen number two) of another, along a peptide or protein cha ...

Preparation

NMF is typically prepared by allowing

methylamine Methylamine is an organic compound with a formula of . This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine. Methylamine is sold as a solution in methanol, ...

to react with methyl formate: :CH₃NH₂ + HCOOCH₃ → CH₃NHCHO + CH₃OH A less common alternative to this process is transamidation involving

: :HCONH₂ + CH₃NH₂ → CH₃NHCHO + NH₃

Uses

NMF is a specialized solvent in oil refineries. It is a precursor in specialized amidation reactions where formamide would not be suitable. These reactions can generally be categorized by the following equation: :R-Lg + CH₃NHCHO → R-NCH₃CHO + H-Lg (where Lg is a leaving group).

Laboratory uses

NMF is the precursor to methyl isocyanide, a ligand in

coordination chemistry A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or complexing agents. Many ...

. NMF is used as a solvent in Aluminum Electrolytic Capacitors.

References

{{DEFAULTSORT:Methylformamide, N- Formamides Amide solvents Solvents