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]

Chloroacetamide
Names
Preferred IUPAC name
2-Chloroacetamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.068
EC Number
  • 201-174-2
UNII
  • InChI=1S/C2H4ClNO/c3-1-2(4)5/h1H2,(H2,4,5)
    Key: VXIVSQZSERGHQP-UHFFFAOYSA-N
  • InChI=1S/C2H4ClNO/c3-1-2(4)5/h1H2,(H2,4,5)
    Key: VXIVSQZSERGHQP-UHFFFAOYAM
  • ClCC(=O)N
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
  1. 2-Chloroacetamide
  2. Koenig, G.; Lohmar, E.; Rupprich, N. "Chloroacetic Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_537.
  3. Jacobs, W. A.; Heidelberger, M. (1927). "Chloroacetamide". Organic Syntheses. 7: 16. doi:10.15227/orgsyn.007.0016.
  4. Herbicides - Epochem Archived 2008-05-20 at the Wayback Machine
  5. Acetamide, 2-chloro- - Government of Canada Archived 2009-01-31 at the Wayback Machine
  6. "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.
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