Acetamide
| Acetamide | |
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Acetamide |
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Other names
acetic acid amide |
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| Identifiers | |
| CAS number | 60-35-5  |
| PubChem | 178 |
| ChemSpider | 173 |
| UNII | 8XOE1JSO29 |
| DrugBank | DB02736 |
| KEGG | C06244 |
| ChEBI | CHEBI:27856 |
| ChEMBL | CHEMBL16081 |
| Jmol-3D images | Image 1 |
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| 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
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 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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 |
[edit] 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
[edit] 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]
[edit] 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]
[edit] References
- ^ The Merck Index, 11th Edition, 36
- ^ 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
- ^ 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
- ^ 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.
- ^ Acetamide, Mindat.org
- ^ Handbook of Mineralogy
- ^ Chemicals Known to the State to Cause Cancer or Reproductive Toxicity, California Office of Environmental Health Hazard Assessment
