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.
|Preferred IUPAC name
|Systematic IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|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)|
|Vapor pressure||0.08 mmHg at 20 °C|
|Acidity (pKa)||23.5 (in DMSO)|
|NFPA 704 (fire diamond)|
|Flash point||154 °C (309 °F; 427 K) (closed cup)|
|NIOSH (US health exposure limits):|
|TWA 10 ppm (15 mg/m3) [skin]|
IDLH (Immediate danger)
|Carbamic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Formamides are compounds of the type RR′NCHO. One important formamide is dimethylformamide, (CH3)2NCHO.
- HCOOH + NH3 → HCOO−NH+
4 → HCONH2 + H2O
- HCOOCH2CH3 + NH3 → HCONH2 + CH3CH2OH
- CO + NH3 → HCONH2
- CO + CH3OH → HCOOCH3
- HCO2CH3 + NH3 → HCONH2 + CH3OH
Formamide decomposes into carbon monoxide and ammonia at 180 °C.
- HCONH2 → CO + NH3
Traces of hydrogen cyanide (HCN) and water are also observed.
- HC(O)NH2 → HCN + H2O
Niche or laboratory applicationsEdit
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.
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.
Formamide is moderately irritating to the eyes, skin and mucous membranes. Inhalation of large amounts of formamide vapor may require medical attention. It is also a teratogen. Formamide has been shown to exhibit hematoxicity in animals and is considered hazardous by prolonged exposure through inhalation, oral intake and dermal absorption. Formamide should never be handled without proper safety attire including gloves and goggles.
- Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 841. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
The traditional name ‘formamide’ is retained for HCO-NH2 and is the preferred IUPAC name.
- NIOSH Pocket Guide to Chemical Hazards. "#0295". National Institute for Occupational Safety and Health (NIOSH).
- F. G. Bordwell; J. E. Bartmess; 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. (ed.). 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. 97: 86–87. Retrieved 14 June 2014.
- Bipp, H.; Kieczka, H. (2012). "Formamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a12_001.pub2.CS1 maint: multiple names: authors list (link)
- Vimal K. Kamineni; Yuri M. Lvov; 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.
- Thauer, R. K. (1998). "Biochemistry of Methanogenesis: a Tribute to Marjory Stephenson". Microbiology. 144: 2377–2406. doi:10.1099/00221287-144-9-2377. PMID 9782487.
- 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.
- TOXNet Formamide HSDB: Formamide
- Warheit DB, Kinney LA, Carakostas MC, Ross PE (1989). "Inhalation toxicity study of formamide in rats". Fundamental and Applied Toxicology. 13 (4): 702–713. doi:10.1093/toxsci/13.4.702. PMID 2620791.
- MSDS for formamide, hazard.com
- Lab use of formamide, University of Bath
-  Archived 2015-07-10 at the Wayback Machine ECHA Formamide