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 | 2000 g L-1[1] |
| Solubility | ethanol 500 g L-1[1] pyridine 166.67 g L-1[1] soluble in chloroform, glycerol, benzene[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.[2] 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:[3]
- CH3COONH4 → CH3C(O)NH2 + H2O
In industry, it is typically obtained by the above reaction, or by the hydrolysis of acetonitrile, a byproduct of the production of acrylonitrile:[2]
- 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]
References
- ^ a b c d The Merck Index, 14th Edition, 36
- ^ a b Cheung, H.; Tanke, R. S.; Torrence, G. P. (2005), "Acetic Acid", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a01_045.pub2
- ^ Coleman, G. H.; Alvarado, A. M. (1923), "Acetamide", Org. Synth. 3: 3; Coll. Vol. 1: 3
- ^ Hollis, J. M.; Lovas, F. J.; Remijan, A. J.; Jewell, P. R.; Ilyushin, V. V.; Kleiner, I. (2006). "Detection of Acetamide (CH3CONH2): The Largest Interstellar Molecule with a Peptide Bond" (pdf). The Astrophysical Journal 643 (1): L25–L28. Bibcode:2006ApJ...643L..25H. doi:10.1086/505110.
- ^ "Acetamide". Mindat.org.
- ^ "Acetamide" (pdf). Handbook of Mineralogy. RRUFF Project.
External links
- International Chemical Safety Card 0233
- "Acetamide". Webmineral.org.
