Chloroacetamide
Chloroacetamide (2-chloroacetamide) is a chlorinated organic compound with the molecular formula ClCH2CONH2. Chloroacetamide is a colorless solid although older samples appear yellow. It has a characteristic odor and is readily soluble in water.[1]
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| IUPAC name
2-Chloroacetamide | |
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| ECHA InfoCard | 100.001.068  |
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| Properties | |
| C2H4ClNO | |
| Molar mass | 93.51 g·mol−1 |
| Appearance | Colorless or yellow crystals |
| Melting point | 120 °C (248 °F; 393 K) |
| 90 g/L at 25°C | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Production
Chloroacetamide is produced by ammonolysis of esters of chloroacetic acid:[2][3]
- ClCH2CO2CH3 + NH3 → ClCH2C(O)NH2 + CH3OH
Uses
Chloroacetamide has been used as an herbicide,[4] preservative.[5] and in the manufacturing of pharmaceuticals.
Hazards
Chloroacetamide is toxic, irritates eyes and skin, and may cause an allergic reaction. It is suspected of reproductive toxicity and teratogenicity.[6]
See also
References
- 2-CHLOROACETAMIDE
- Koenig, G.; Lohmar, E.; Rupprich, N. "Chloroacetic Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_537.
- Jacobs, W. A.; Heidelberger, M. (1927). "Chloroacetamide". Organic Syntheses. 7: 16. doi:10.15227/orgsyn.007.0016.
- Herbicides - Epochem Archived 2008-05-20 at the Wayback Machine
- Acetamide, 2-chloro- - Government of Canada Archived 2009-01-31 at the Wayback Machine
- "DECISION du 14 juin 2012" (PDF) (in French). Agence Nationale de Sécurité du Médicament et des Produits de Santé. Cite journal requires
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