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Acetamide

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Acetamide
Names
IUPAC names Acetamide
Ethanamide
Other names acetic acid amide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.430 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)Key: DLFVBJFMPXGRIB-UHFFFAOYSA-N
  • InChI=1/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)Key: DLFVBJFMPXGRIB-UHFFFAOYAC
SMILES
  • O=C(N)C
Properties
Chemical formula C2H5NO
Molar mass 59.068 g·mol
Density 1.16 g/cm³
Boiling point 222 °C (432 °F; 495 K)
Solubility in water 2 g/mL
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium
3 1 1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Acetamide (IUPAC: ethanamide) is an organic compound with the formula CH3CONH2. It is the simplest amide derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent. The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide.

Production and use

Acetamide can be produced in the laboratory by dehydrating ammonium acetate:

CH3COONH4 → CH3C(O)NH2 + H2O

In industry, it is typically obtained by hydrolysis of acetonitrile, a byproduct of the production of acrylonitrile:

CH3CN + H2O → CH3C(O)NH2

Occurrence

Acetamide has been detected near the center of the Milky Way galaxy. This finding is potentially significant because acetamide has an amide bond, similar to the essential bond between amino acids in proteins. This finding lends support to the theory that organic molecules that can lead to life (as we know it on Earth) can form in space.

In addition, acetamide is found infrequently on burning coal dumps, as a mineral of the same name.

Safety

In the U.S., the California Environmental Protection Agency added acetamide to the list of compounds known to cause cancer or reproductive toxicity, for the purposes of Proposition 65.

References

  1. The Merck Index, 11th Edition, 36
  2. G. H. Coleman and A. M. Alvarado (1941). "Acetamide". Organic Syntheses; Collected Volumes, vol. 1, p. 3.
  3. Hosea Cheung, Robin S. Tanke, G. Paul Torrence “Acetic Acid” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a01_045
  4. J. M. Hollis, F. J. Lovas, Anthony J. Remijan, P. R. Jewell, V. V. Ilyushin, and I. Kleiner (2006). "Detection of Acetamide (CH3CONH2): The Largest Interstellar Molecule with a Peptide Bond". The Astrophysical Journal. 643 (2): L25 – L28. Bibcode:2006ApJ...643L..25H. doi:10.1086/505110.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. Acetamide, Mindat.org
  6. Handbook of Mineralogy
  7. Chemicals Known to the State to Cause Cancer or Reproductive Toxicity, California Office of Environmental Health Hazard Assessment

External links

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