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Structural formula of the formamide molecule
Ball and stick model of formamide
Space-filling model of the formamide molecule
IUPAC name
Other names
75-12-7 YesY
ChEBI CHEBI:48431 YesY
ChEMBL ChEMBL266160 YesY
ChemSpider 693 YesY
Jmol 3D model Interactive image
KEGG C00488 YesY
PubChem 713
Molar mass 45.04 g/mol
Appearance Colorless, oily liquid[1]
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)
Vapor pressure 0.08 mmHg at 20 °C
Acidity (pKa) 23.5 (in DMSO)[2]
Vapor pressure {{{value}}}
Related compounds
Related compounds
Carbamic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Formamide, also known as methanamide, is an amide derived from formic acid. It is a clear liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs, other pharmaceuticals, herbicides, pesticides and 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.[3]

Formamide will begin to partially decompose into carbon monoxide and ammonia at 180 °C together with traces of hydrogen cyanide (HCN) and water. In the presence of solid acid catalysts, formamide yields HCN in high yield:[4]

low temperature: HC(O)NH2 → CO + NH3
high temperature, acid-catalyzed: HC(O)NH2 → HCN + H2O


Historical production

In the past, formamide was produced by treating formic acid with ammonia, which produces ammonium formate, which in turn yield formamide upon heating:[5]


Formamide is also generated by aminolysis of ethyl formate:[6]


Modern production

The current industrial process for the manufacture of formamide involves either the carbonylation of ammonia:[3]


An alternative two-stage process involves the aminolysis of methyl formate, which is formed from carbon monoxide and methanol:

HCO2CH3 + NH3 → HC(O)NH2 + CH3OH


Formamide is used in the industrial production of hydrogen cyanide. It is also used as a solvent for processing various polymers such as polyacrylonitrile.[4]

Niche or laboratory applications

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.[7]

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

Hypothetical biochemistry

Formamide has also 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 can be formed by the reaction of hydrogen cyanide and water, has a large dipole moment, and dissolves almost everything that will dissolve in water.[8]

RNA base creation

Formamide has been shown to create guanine at 130 °C in the presence of ultra violet light.[9]


Formamide is moderately irritating to the eyes, skin and mucous membranes.[10] Inhalation of large amounts of formamide vapor may require medical attention.[11][12] It is also a teratogen.[13] Formamide has been shown to exhibit hematoxicity in animals and is considered hazardous by prolonged exposure through inhalation, oral intake and dermal absorption.[14] Formamide should never be handled without proper safety attire including gloves and goggles.


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  3. 3.0 3.1 Hohn, A. (1999). "Formamide". In Kroschwitz, Jacqueline I. Kirk-Othmer Concise Encylclopedia of Chemical Technology (4th ed.). New York: John Wiley & Sons, Inc. pp. 943–944. ISBN 978-0471419617.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  4. 4.0 4.1 Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  5. Lorin, M. (1864). "Preparation of Formamide by means of Formiates and Oxalates". The Chemical News and Journal of Physical Science. IX: 291. Retrieved 14 June 2014.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  6. Phelps, I.K.; Deming, C.D. (1908). "The Preparation of Formamide from Ethyl Formate and Ammonium Hydroxide". The Chemical News and Journal of Physical Science. XCVII: 86–87. Retrieved 14 June 2014.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  7. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  8. Committee On The Limits Of Organic Life In Planetary Systems (2007). The Limits of Organic Life in Planetary Systems. Washington, DC: The National Academies Press. p. 74. ISBN 0-309-66906-5. Retrieved 2012-08-29.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  9. "Origin of Life: Adding UV Light Helps Form 'Missing G' of RNA Building Blocks". Science Daily. June 14, 2010.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  10. TOXNet Formamide HSDB: Formamide
  11. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  12. MSDS for formamide,
  13. Lab use of formamide, University of Bath
  14. [1] ECHA Formamide