Acetamide

Acetamide
IUPAC name

Acetamide
Ethanamide
Other names

acetic acid amide
Identifiers
CAS number 60-35-5 Y
PubChem 178
ChemSpider 173 Y
UNII 8XOE1JSO29 Y
DrugBank DB02736
KEGG C06244 Y
ChEBI CHEBI:27856 Y
ChEMBL CHEMBL16081 Y
Jmol-3D images Image 1
Properties
Molecular formula C2H5NO
Molar mass 59.07 g mol−1
Density 1.16 g/cm³
Melting point

79-81 °C, 352-354 K, 174-178 °F
Boiling point

222 °C, 495 K, 432 °F
Solubility in water 2 g/mL[1]
Hazards
MSDS External MSDS
EU Index 616-022-00-4
EU classification Harmful (Xn)
Carc. Cat. 3
R-phrases R40
S-phrases (S2) S36/37
NFPA 704
1
3
1
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

Contents

Production and use

Acetamide can be produced in the laboratory by dehydrating ammonium acetate:[2]

CH3COONH4 → CH3C(O)NH2 + H2O

In industry, it is typically obtained by hydrolysis of acetonitrile, a byproduct of the production of acrylonitrile:[3]

CH3CN + H2O → CH3C(O)NH2

Occurrence

Acetamide has been detected near the center of the Milky Way galaxy.[4] 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.[5][6]

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.[7]

References

  1. ^ The Merck Index, 11th Edition, 36
  2. ^ G. H. Coleman and A. M. Alvarado (1941), "Acetamide", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p003 ; Coll. Vol. 1: 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. 
  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