Chloroacetamide

Chloroacetamide
Names
IUPAC name
2-Chloroacetamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.068
EC Number 201-174-2
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

Chloroacetamide (2-chloroacetamide) is a chlorinated organic compound with the molecular formula CHCl2CONH2. It is used as an herbicide[1] and a preservative.[2] It is a colorless (older samples appear yellow) crystalline substance with characteristic smell, readily soluble in water.[3]

Production

It is produced by ammonolysis of the methyl ester:[4]

ClCH2CO2CH3 + NH3 → ClCH2C(O)NH2 + CH3OH

Hazards

Chloroacetamide is toxic, irritates eyes and skin, and may cause an allergic reaction. It is suspected of reproductive toxicity and teratogenicity.[5] It decomposes when heated above 225 °C and creates toxic gases including chlorine and nitrogen oxides.[3]

See also

References

  1. ↑ Herbicides - Epochem Archived 2008-05-20 at the Wayback Machine.
  2. ↑ Acetamide, 2-chloro- - Government of Canada Archived 2009-01-31 at the Wayback Machine.
  3. 1 2 2-CHLOROACETAMIDE
  4. ↑ Koenig, G.; Lohmar, E.; Rupprich, N., "Chloroacetic Acids", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a06_537
  5. ↑ "DECISION du 14 juin 2012" (PDF) (in French). Agence Nationale de Sécurité du Médicament et des Produits de Santé.
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