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| Names | |||
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| Preferred IUPAC name Formamide[1] | |||
| Systematic IUPAC name Methanamide | |||
| Other names Carbamaldehyde | |||
| Identifiers | |||
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3D model (JSmol) | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.000.766 | ||
| EC Number |
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| KEGG |
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| UNII | |||
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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 (inDMSO)[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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Formamide is anamide derived fromformic acid. It is a colorless liquid which is miscible with water and has anammonia-like odor. It is chemical feedstock for the manufacture ofsulfa drugs and otherpharmaceuticals,herbicides andpesticides, and in the manufacture ofhydrocyanic acid. It has been used as asoftener for paper and fiber. It is asolvent for manyionic compounds. It has also been used as a solvent forresins andplasticizers.[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 isdimethylformamide, (CH3)2NCHO.
In the past, formamide was produced by treatingformic acid withammonia, which producesammonium formate, which in turn yields formamide upon heating:[6]
Formamide is also generated byaminolysis ofethyl formate:[7]
The current industrial process for the manufacture of formamide involves thecarbonylation of ammonia:[4]
An alternative two-stage process involves the ammonolysis ofmethyl formate, which is formed from carbon monoxide andmethanol:
Formamide is used in the industrial production ofhydrogen cyanide. It is also used as a solvent for processing various polymers such aspolyacrylonitrile.[8]
It is also known that formamide is an excellent swelling agent forcellulosic fibres,[9] and is used in some specific wood-related applications.
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 tohydrogen cyanide (HCN) and water instead:
The same effect occurs in the presence ofsolid acid catalysts.[8]
Formamide is a constituent of cryoprotectantvitrification mixtures used for cryopreservation of tissues andorgans.
Formamide is also used as an RNA stabiliser ingel electrophoresis by deionizing RNA. In capillary electrophoresis, it is used for stabilizing (single) strands of denatured DNA.
Another use is to add it insol-gel solutions in order to avoid cracking duringsintering.
Formamide, in its pure state, has been used as an alternative solvent for the electrostaticself-assembly of polymer nanofilms.[10]
Formamide is used to prepare primary amines directly from ketones via their N-formyl derivatives, using theLeuckart reaction.
Formamides are intermediates in themethanogenesis cycle.
Formamide has been proposed as an alternativesolvent 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.[12]
Formamide has been shown to convert to traces ofguanine upon heating in the presence of ultraviolet light.[13]
Several prebiotic chemical reactions producing amino acid derivatives have been shown to take place in formamide.[14] Similar scenarios implicatethioformamide.[15]
Contact with skin and eyes is not recommended. With anLD50 of grams per kg, formamide is of low acute toxicity. It also has low mutagenicity.[8]
Formamide is classified as toxic to reproductive health.[16]
The traditional name 'formamide' is retained for HCO-NH2 and is the preferred IUPAC name.
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