|Jmol-3D images||Image 1|
|Molar mass||45.04 g/mol|
|Appearance||Colorless, oily liquid|
|Melting point||2 to 3 °C (36 to 37 °F; 275 to 276 K)|
|Boiling point||210 °C (410 °F; 483 K)|
|Solubility in water||Miscible|
|Vapor pressure||0.08 mmHg at 20 °C|
|Acidity (pKa)||23.5 (in DMSO)|
|Flash point||154 °C (309 °F; 427 K) (closed cup)|
|Related compounds||Carbamic acid
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
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.
Formamide will begin to partially decompose into carbon monoxide and ammonia at 180 °C. When heated strongly, formamide decomposes to hydrogen cyanide (HCN) and water vapor.
- HCOOCH2CH3 + NH3 → HCONH2 + CH3CH2OH
- CO + NH3 → HCONH2
- HCOOCH3 + NH3 → HCONH2 + CH3OH
with the possibility of the resulting methanol being recycled into more methyl formate, by reaction with carbon monoxide:
- CO + CH3OH → HCOOCH3
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.
Formamide is used to prepare primary amines directly from ketones via their N-formyl derivatives, using the Leuckart reaction.
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.
RNA base creation
Formamide is highly corrosive on contact with skin or eyes and may be deadly if ingested. Inhalation of large amounts of formamide vapor may require medical attention. It is also a teratogen. Formamide should never be handled without proper safety attire including gloves and goggles. There is a small risk of decomposition into hydrogen cyanide and water.
- CDC - NIOSH Pocket Guide to Chemical Hazards
- F. G. Bordwell, J. E. Bartmess and J. A. Hautala (1978). "Alkyl effects on equilibrium acidities of carbon acids in protic and dipolar aprotic media and the gas phase". J. Org. Chem. 43 (16): 3095–3101. doi:10.1021/jo00410a001.
- 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.
- 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.
- 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.
- Vimal K. Kamineni, Yuri M. Lvov, and Tabbetha A. Dobbins (2007). "Layer-by-Layer Nanoassembly of Polyelectrolytes Using Formamide as the Working Medium". Langmuir 23 (14): 7423–7427. doi:10.1021/la700465n. PMID 17536845.
- 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.
- "Origin of Life: Adding UV Light Helps Form 'Missing G' of RNA Building Blocks". Science Daily. June 14, 2010.
- Warheit DB1, Kinney LA, Carakostas MC, Ross PE (1989). "Inhalation toxicity study of formamide in rats". FUNDAMENTAL AND APPLIED TOXICOLOGY 13 (4): 702–713. PMID 2620791.
- MSDS for formamide, hazard.com
- Lab use of formamide, University of Bath