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

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

and secondary amide 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 (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

. 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 pesticides, ...

and

dimethylformamide Dimethylformamide, DMF is an organic compound with the chemical formula . Its structure is . Commonly abbreviated as DMF (although this initialism is sometimes used for 2,5-dimethylfuran, dimethylfuran, or dimethyl fumarate), this colourless liqui ...

(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 (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

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

Because of slow rotation about the N-C(O) bond, NMF exists as two rotamers that can be distinguished by

NMR spectroscopy Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy or magnetic resonance spectroscopy (MRS), is a spectroscopic technique based on re-orientation of atomic nuclei with non-zero nuclear spins in an external magnetic f ...

. The two principal

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

s for one of these rotamers is shown: :: This description highlights the partial

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

that exists between the

carbonyl In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double bond, double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such a ...

carbon and nitrogen, which raises the 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'', an upcoming film by Sally Potter * ''Alma'' (Oswald de Andrade novel), 1922 * ''Alma'' (Le Clézio novel), 2017 * ''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, also known as methanamine, 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 ...

to react with

methyl formate Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of a carboxylate ester, it is a colourless liquid with an ethereal odour, high vapor pressure, and low surface tension. The gas form is odourl ...

: :CH₃NH₂ + HCOOCH₃ → HCONHCH₃ + CH₃OH A less common alternative to this process is transamidation involving

: :HCONH₂ + CH₃NH₂ → HCONHCH₃ + 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 In organic chemistry, a leaving group typically means a Chemical species, molecular fragment that departs with an electron, electron pair during a reaction step with heterolysis (chemistry), heterolytic bond cleavage. In this usage, a ''leaving gr ...

Laboratory uses

NMF is the precursor to

methyl isocyanide Methyl isocyanide or isocyanomethane is an organic compound and a member of the isocyanide family. This colorless liquid is isomeric and isoelectronic to methyl cyanide (acetonitrile), but its reactivity is very different. In contrast to the faint ...

, a ligand in

coordination chemistry A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ' ...

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

References

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