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Names | |||
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Preferred IUPAC name Formamide [1] | |||
Systematic IUPAC name Methanamide | |||
Other names Carbamaldehyde | |||
Identifiers | |||
3D model (JSmol) | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.000.766 | ||
KEGG | |||
PubChem CID | |||
UNII | |||
CompTox Dashboard (EPA) | |||
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Properties | |||
CH3NO | |||
Molar mass | 45.04 g/mol | ||
Appearance | Colorless, oily liquid [2] | ||
Density | 1.133 g/cm3 | ||
Melting point | 2 to 3 °C (36 to 37 °F; 275 to 276 K) | ||
Boiling point | 210 °C (410 °F; 483 K) | ||
Miscible | |||
Vapor pressure | 0.08 mmHg at 20 °C | ||
Acidity (pKa) | 23.5 (in DMSO) [3] | ||
−2.19×10−5 cm3/mol | |||
Hazards | |||
NFPA 704 (fire diamond) | |||
Flash point | 154 °C (309 °F; 427 K) (closed cup) | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible) | none [2] | ||
REL (Recommended) | TWA 10 ppm (15 mg/m3) [skin] [2] | ||
IDLH (Immediate danger) | N.D. [2] | ||
Related compounds | |||
Related compounds | Carbamic acid Dimethylformamide | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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 in the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers. [4] Some astrobiologists suggest that it may be an alternative to water as the main solvent in other forms of life. [5]
Formamides are compounds of the type RR′NCHO. One important formamide is dimethylformamide, (CH3)2NCHO.
In the past, formamide was produced by treating formic acid with ammonia, which produces ammonium formate, which in turn yields formamide upon heating: [6]
Formamide is also generated by aminolysis of ethyl formate: [7]
The current industrial process for the manufacture of formamide involves the carbonylation of ammonia: [4]
An alternative two-stage process involves the ammonolysis of methyl formate, which is formed from carbon monoxide and methanol:
Formamide is used in the industrial production of hydrogen cyanide. It is also used as a solvent for processing various polymers such as polyacrylonitrile. [8]
Formamide decomposes into carbon monoxide and ammonia when heated above 100 °C.
The reaction is slow below 160 °C, but accelerates thereafter. At very high temperatures, the reaction products shift to hydrogen cyanide (HCN) and water instead:
The same effect occurs in the presence of solid acid catalysts. [8]
Formamide is a constituent of cryoprotectant vitrification mixtures used for cryopreservation of tissues and organs.
Formamide is also used as an RNA stabiliser in gel electrophoresis 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.
Formamide, in its pure state, has been used as an alternative solvent for the electrostatic self-assembly of polymer nanofilms. [9]
Formamide is used to prepare primary amines directly from ketones via their N-formyl derivatives, using the Leuckart reaction.
Formamides are intermediates in the methanogenesis cycle.
Formamide has been proposed as an alternative solvent 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. [11]
Formamide has been shown to convert to traces of guanine upon heating in the presence of ultraviolet light. [12]
Several prebiotic chemical reactions producing amino acid derivatives have been shown to take place in formamide. [13]
Contact with skin and eyes is not recommended. With an LD50 of grams per kg, formamide is of low acute toxicity. It also has low mutagenicity. [8]
Formamide is classified as toxic to reproductive health. [14]
The Miller–Urey experiment (or Miller experiment) was an experiment in chemical synthesis carried out in 1952 that simulated the conditions thought at the time to be present in the atmosphere of the early, prebiotic Earth. It is seen as one of the first successful experiments demonstrating the synthesis of organic compounds from inorganic constituents in an origin of life scenario. The experiment used methane (CH4), ammonia (NH3), hydrogen (H2), in ratio 2:2:1, and water (H2O). Applying an electric arc (the latter simulating lightning) resulted in the production of amino acids.
Purine is a heterocyclic aromatic organic compound that consists of two rings fused together. It is water-soluble. Purine also gives its name to the wider class of molecules, purines, which include substituted purines and their tautomers. They are the most widely occurring nitrogen-containing heterocycles in nature.
Adenine is a purine nucleobase. It is one of the four nucleobases in the nucleic acids of DNA, the other three being guanine (G), cytosine (C), and thymine (T). Adenine derivatives have various roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD), flavin adenine dinucleotide (FAD) and Coenzyme A. It also has functions in protein synthesis and as a chemical component of DNA and RNA. The shape of adenine is complementary to either thymine in DNA or uracil in RNA.
Hydrogen cyanide is a chemical compound with the formula HCN and structural formula H−C≡N. It is a highly toxic and flammable liquid that boils slightly above room temperature, at 25.6 °C (78.1 °F). HCN is produced on an industrial scale and is a highly valued precursor to many chemical compounds ranging from polymers to pharmaceuticals. Large-scale applications are for the production of potassium cyanide and adiponitrile, used in mining and plastics, respectively. It is more toxic than solid cyanide compounds due to its volatile nature. A solution of hydrogen cyanide in water, represented as HCN, is called hydrocyanic acid. The salts of the cyanide anion are known as cyanides.
Sodium cyanide is a poisonous compound with the formula NaCN. It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to the high toxicity of this salt. Its main application, in gold mining, also exploits its high reactivity toward metals. It is a moderately strong base.
Formic acid, systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure H−C(=O)−O−H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts and the anion derived from formic acid are called formates. Industrially, formic acid is produced from methanol.
In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group. The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH3CH2C≡N is called "propionitrile". The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.
Benzonitrile is the chemical compound with the formula C6H5(CN), abbreviated PhCN. This aromatic organic compound is a colorless liquid with a sweet bitter almond odour. It is mainly used as a precursor to the resin benzoguanamine.
Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of a carboxylate ester, it is a colorless liquid with an ethereal odour, high vapor pressure, and low surface tension. It is a precursor to many other compounds of commercial interest.
Methylamine is an organic compound with a formula of CH3NH2. 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.
Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).
The Strecker amino acid synthesis, also known simply as the Strecker synthesis, is a method for the synthesis of amino acids by the reaction of an aldehyde with cyanide in the presence of ammonia. The condensation reaction yields an α-aminonitrile, which is subsequently hydrolyzed to give the desired amino acid. The method is used for the commercial production of racemic methionine from methional.
An inorganic nonaqueous solvent is a solvent other than water, that is not an organic compound. These solvents are used in chemical research and industry for reactions that cannot occur in aqueous solutions or require a special environment. Inorganic nonaqueous solvents can be classified into two groups, protic solvents and aprotic solvents. Early studies on inorganic nonaqueous solvents evaluated ammonia, hydrogen fluoride, sulfuric acid, as well as more specialized solvents, hydrazine, and selenium oxychloride.
The Leuckart reaction is the chemical reaction that converts aldehydes or ketones to amines by reductive amination in the presence of heat. The reaction, named after Rudolf Leuckart, uses either ammonium formate or formamide as the nitrogen donor and reducing agent. It requires high temperatures, usually between 120 and 130 °C; for the formamide variant, the temperature can be greater than 165 °C.
Benzylamine is an organic chemical compound with the condensed structural formula C6H5CH2NH2 (sometimes abbreviated as PhCH2NH2 or BnNH2). It consists of a benzyl group, C6H5CH2, attached to an amine functional group, NH2. This colorless water-soluble liquid is a common precursor in organic chemistry and used in the industrial production of many pharmaceuticals. The hydrochloride salt was used to treat motion sickness on the Mercury-Atlas 6 mission in which NASA astronaut John Glenn became the first American to orbit the Earth.
Ammonium formate, NH4HCO2, is the ammonium salt of formic acid. It is a colorless, hygroscopic, crystalline solid.
Ammonium cyanide is an unstable inorganic compound with the formula NH4CN.
Barium cyanide is a chemical compound with the formula Ba(CN)2. It is synthesized by the reaction of hydrogen cyanide and barium hydroxide in water or petroleum ether. It is a white crystalline salt.
Formamide-based prebiotic chemistry is a reconstruction of the beginnings of life on Earth, assuming that formamide could accumulate in sufficiently high amounts to serve as the building block and reaction medium for the synthesis of the first biogenic molecules.
A proto-metabolism is a series of linked chemical reactions in a prebiotic environment that preceded and eventually turned into modern metabolism. Combining ongoing research in astrobiology and prebiotic chemistry, work in this area focuses on reconstructing the connections between potential metabolic processes that may have occurred in early Earth conditions. Proto-metabolism is believed to be simpler than modern metabolism and the Last Universal Common Ancestor (LUCA), as simple organic molecules likely gave rise to more complex metabolic networks. Prebiotic chemists have demonstrated abiotic generation of many simple organic molecules including amino acids, fatty acids, simple sugars, and nucleobases. There are multiple scenarios bridging prebiotic chemistry to early metabolic networks that occurred before the origins of life, also known as abiogenesis. In addition, there are hypotheses made on the evolution of biochemical pathways including the metabolism-first hypothesis, which theorizes how reaction networks dissipate free energy from which genetic molecules and proto-cell membranes later emerge. To determine the composition of key early metabolic networks, scientists have also used top-down approaches to study LUCA and modern metabolism.
The traditional name 'formamide' is retained for HCO-NH2 and is the preferred IUPAC name.