Back فورماميد Arabic فورمامید AZB Фармамід Byelorussian Formamida Catalan Formamid Czech Formamid German Μεθαναμίδιο Greek Formiamido Esperanto Formamida Spanish Formamiid Estonian

Formamide

Formamide
Structural formula of the formamide molecule
Ball and stick model of formamide
Ball and stick model of formamide
Space-filling model of the formamide molecule
Space-filling model of the formamide molecule
Names
Preferred IUPAC name
Formamide[1]
Systematic IUPAC name
Methanamide
Other names
Carbamaldehyde
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.766 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3) checkY
    Key: ZHNUHDYFZUAESO-UHFFFAOYSA-N checkY
  • InChI=1/CH3NO/c2-1-3/h1H,(H2,2,3)
    Key: ZHNUHDYFZUAESO-UHFFFAOYAQ
  • O=CN
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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 154 °C (309 °F; 427 K) (closed cup)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[2]
REL (Recommended)
 TWA 10 ppm (15 mg/m3) [skin][2]
IDLH (Immediate danger)
 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.

  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.
  2. ^ a b c d 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.
  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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