Formamide

Formamide
Ball and stick model of formamide	Space-filling model of the formamide molecule
Names
	Preferred IUPAC name Formamide
	Systematic IUPAC name Methanamide
	Other names Carbamaldehyde
Identifiers
CAS Number	75-12-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:48431 ;
ChEMBL	ChEMBL266160 ;
ChemSpider	693 ;
ECHA InfoCard	100.000.766
IUPHAR/BPS	4739;
KEGG	C00488 ;
PubChem CID	713;
UNII	4781T907ZS ;
CompTox Dashboard (EPA)	DTXSID8025337 ;
	InChI InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3) Key: ZHNUHDYFZUAESO-UHFFFAOYSA-N ; InChI=1/CH3NO/c2-1-3/h1H,(H2,2,3) Key: ZHNUHDYFZUAESO-UHFFFAOYAQ;
	SMILES O=CN;
Properties
Chemical formula	CH3NO
Molar mass	45.04 g/mol
Appearance	Colorless, oily liquid
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)
Solubility in water	Miscible
Vapor pressure	0.08 mmHg at 20 °C
Acidity (pKa)	23.5 (in DMSO)
Magnetic susceptibility (χ)	−2.19×10−5 cm3/mol
Hazards
NFPA 704 (fire diamond)	2 1 0
Flash point	154 °C (309 °F; 427 K) (closed cup)
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	TWA 10 ppm (15 mg/m3) [skin]
IDLH (Immediate danger)	N.D.
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). verify (what is ?) Infobox references

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.

[iupac2013-1] 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.

[PGCH-2] NIOSH Pocket Guide to Chemical Hazards. "#0295". National Institute for Occupational Safety and Health (NIOSH).

[3] 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.

[KirkOthmer-4] 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.

[5] "How to improve the search for aliens". The Economist.

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