Formamide is an

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 i ...

derived from

formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Est ...

. It is a colorless liquid which is miscible with water and has an

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous ...

-like odor. It is chemical feedstock for the manufacture of

sulfa drug Sulfonamide is a functional group (a part of a molecule) that is the basis of several groups of drugs, which are called sulphonamides, sulfa drugs or sulpha drugs. The original antibacterial sulfonamides are synthetic (nonantibiotic) antimi ...

s and other

pharmaceutical A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacotherapy) is an important part of the medical field and ...

herbicide Herbicides (, ), also commonly known as weedkillers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...

s and

pesticides Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and la ...

, and in the manufacture of

hydrocyanic acid Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structure . It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at . HCN is produced on an in ...

. It has been used as a softener for paper and fiber. It is 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 ...

for many

ionic compound In chemistry, an ionic compound is a chemical compound composed of ions held together by electrostatic forces termed ionic bonding. The compound is neutral overall, but consists of positively charged ions called cations and negatively charged ...

s. It has also been used as a solvent for resins and

plasticizers A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plastic ...

. Some astrobiologists suggest that it may be an alternative to water as the main solvent in other forms of life. Formamides are compounds of the type RR′NCHO. One important formamide is

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 ...

, (CH₃)₂NCHO.

Production

Historical production

In the past, formamide was produced by treating

with

, which produces ammonium formate, which in turn yields formamide upon heating: :HCOOH + NH₃ → HCOO⁻ :HCOO⁻ → HCONH₂ + H₂O Formamide is also generated by

aminolysis In chemistry, aminolysis (/am·i·nol·y·sis/) is any chemical reaction in which a molecule is Chemical decomposition, lysed (split into two parts) by reacting with ammonia () or an amine (any molecule containing a nitrogen atom with a lone pair, ...

ethyl formate Ethyl formate is an ester formed when ethanol (an alcohol) reacts with formic acid (a carboxylic acid). Ethyl formate has the characteristic smell of rum and is also partially responsible for the flavor of raspberries. It occurs naturally in the b ...

: :HCOOCH₂CH₃ + NH₃ → HCONH₂ + CH₃CH₂OH

Modern production

The current industrial process for the manufacture of formamide involves the

carbonylation Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbon ...

of ammonia: : CO + NH₃ → HCONH₂ An alternative two-stage process involves the ammonolysis of

methyl formate Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of an ester, it is a colorless liquid with an ethereal odour, high vapor pressure, and low surface tension. It is a precursor to many other co ...

, which is formed from carbon monoxide and

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is ...

: :CO + CH₃OH → HCOOCH₃ :HCO₂CH₃ + NH₃ → HCONH₂ + CH₃OH

Applications

Formamide is used in the industrial production of

hydrogen cyanide Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structure . It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at . HCN is produced on a ...

. It is also used as a solvent for processing various polymers such as

polyacrylonitrile Polyacrylonitrile (PAN), also known as polyvinyl cyanide and Creslan 61, is a synthetic, semicrystalline organic polymer resin, with the linear formula (C3H3N)n. Though it is thermoplastic, it does not melt under normal conditions. It degrades bef ...

Reactions

Formamide decomposes into carbon monoxide and ammonia at 180 °C. :HCONH₂ → CO + NH₃ Traces of

(HCN) and water are also observed. In the presence of

solid acid Solid is one of the four fundamental states of matter (the others being liquid, gas, and plasma). The molecules in a solid are closely packed together and contain the least amount of kinetic energy. A solid is characterized by structural ...

catalysts, formamide dehydrates to HCN: :HC(O)NH₂ → HCN + H₂O

Niche or laboratory applications

Formamide is a constituent of cryoprotectant

vitrification Vitrification (from Latin ''vitreum'', "glass" via French ''vitrifier'') is the full or partial transformation of a substance into a glass, that is to say, a non- crystalline amorphous solid. Glasses differ from liquids structurally and glasses po ...

mixtures used for cryopreservation of tissues and

organ Organ may refer to: Biology * Organ (biology), a part of an organism Musical instruments * Organ (music), a family of keyboard musical instruments characterized by sustained tone ** Electronic organ, an electronic keyboard instrument ** Hammond ...

s. Formamide is also used as an RNA stabiliser in

gel electrophoresis Gel electrophoresis is a method for separation and analysis of biomacromolecules ( DNA, RNA, proteins, etc.) and their fragments, based on their size and charge. It is used in clinical chemistry to separate proteins by charge or size (IEF ...

by deionizing RNA. In capillary electrophoresis, it is used for stabilizing (single) strands of denatured DNA. Another use is to add it in sol-gel solutions in order to avoid cracking during

sintering Clinker nodules produced by sintering Sintering or frittage is the process of compacting and forming a solid mass of material by pressure or heat without melting it to the point of liquefaction. Sintering happens as part of a manufacturing ...

. Formamide, in its pure state, has been used as an alternative solvent for the electrostatic

self-assembly Self-assembly is a process in which a disordered system of pre-existing components forms an organized structure or pattern as a consequence of specific, local interactions among the components themselves, without external direction. When the ...

of polymer nanofilms. Formamide is used to prepare primary amines directly from ketones via their N-formyl derivatives, using the Leuckart reaction.

Biochemistry

Formamides are intermediates in the

methanogenesis Methanogenesis or biomethanation is the formation of methane coupled to energy conservation by microbes known as methanogens. Organisms capable of producing methane for energy conservation have been identified only from the domain Archaea, a group ...

cycle.

Prebiotic chemistry

Formamide has been proposed as an alternative

to water, perhaps with the ability to support life with alternative biochemistries to that currently found on Earth. It forms by the hydrolysis of hydrogen cyanide. With a large dipole moment, its solvation properties are similar to those of water. Formamide has been shown to convert to traces of

guanine Guanine () ( symbol G or Gua) is one of the four main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine ( uracil in RNA). In DNA, guanine is paired with cytosine. The guanine nucleoside is ...

upon heating in the presence of ultraviolet light.

Safety

Like all organic compounds, contact with skin and eyes is not recommended. With an

LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a toxin, radiation, or pathogen. The value of LD50 for a substance is the ...

of grams per kg, formamide is of low acute toxicity. It also has low mutagenicity. Formamide is classified as toxic to reproductive health.

References

{{Authority control Amide solvents