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Formamide
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
Formamide[1] | |||
| Systematic IUPAC name
Methanamide | |||
| Other names
Carbamaldehyde
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| Identifiers | |||
3D model (JSmol)
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| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.000.766 | ||
| KEGG | |||
PubChem CID
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| 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)
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none[2] | ||
REL (Recommended)
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TWA 10 ppm (15 mg/m3) [skin][2] | ||
IDLH (Immediate danger)
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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).
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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.
- ^ 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.
- ^ a b c d 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 Encyclopedia of Chemical Technology (4th ed.). New York: John Wiley & Sons, Inc. pp. 943–944. ISBN 978-0471419617.
- ^ "How to improve the search for aliens". The Economist.
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