Chloroacetamide (2-chloroacetamide) is a chlorinated organic compound with the molecular formula ClCH2CONH2. It is a colorless solid although older samples appear yellow. It has a characteristic odor and is readily soluble in water.[2] It has the structure Cl−CH2−C(=O)−NH2.
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| Names | |
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| Preferred IUPAC name
2-Chloroacetamide | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.001.068 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| ClCH2CONH2 | |
| Molar mass | 93.51 g·mol−1 |
| Appearance | Colorless crystals or white fine powder[1] (yellow if impure) |
| Odor | Characteristic |
| Density | 1.58 g/cm3 at 20 °C[1] |
| Melting point | 120 °C (248 °F; 393 K) |
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| Vapor pressure | 0.07 hPa at 20 °C[1] |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Very toxic. It is suspected of reproductive toxicity and teratogenicity. |
Ingestion hazards
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Very toxic |
Inhalation hazards
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Very toxic |
Eye hazards
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Irritation |
Skin hazards
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Irritation |
| GHS labelling: | |
 
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| Danger | |
| H301, H317, H361, H402 | |
| P201, P202, P261, P264, P270, P272, P273, P280, P301+P310+P330, P302+P352, P308+P313, P333+P313, P405, P501 | |
| Flash point | 170 °C (338 °F; 443 K) |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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138 mg/kg (oral, rat) >2000 mg/kg (skin, rat) |
LC50 (median concentration)
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19.8 mg/l, 96 h (Carassius auratus (goldfish)) |
| Safety data sheet (SDS) | [1] |
| Related compounds | |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Production
editChloroacetamide is produced by ammonolysis of esters of chloroacetic acid:[3][4]
- ClCH2CO2CH3 + NH3 → ClCH2C(O)NH2 + CH3OH
Uses
editChloroacetamide has been used as an herbicide,[5] preservative.[6] and in the manufacturing of pharmaceuticals.
Hazards
editChloroacetamide is toxic, irritates eyes and skin, and may cause an allergic reaction. It is suspected of reproductive toxicity and teratogenicity.[7]
See also
edit- Novosphingobium chloroacetimidivorans, a bacterium named after its ability to degrade chloroacetamide
References
edit- ^ a b c d e https://www.sigmaaldrich.cn/CN/en/sds/mm/8.02412?userType=anonymous
- ^ 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. ISBN 978-3527306732.
- ^ 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
- ^ "Decisiondu 14 juin 2012" (PDF) (in French). Agence Nationale de Sécurité du Médicament et des Produits de Santé. Archived from the original (PDF) on 2013-05-23. Retrieved 2012-07-03.