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
IUPAC name 2-Chloroacetamide
Identifiers
CAS Number	79-07-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:361034
ChemSpider	6332
ECHA InfoCard	100.001.068
EC Number	201-174-2
PubChem CID	6580
UNII	2R97846T1L
CompTox Dashboard (EPA)	DTXSID9041570
InChI 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
SMILES ClCC(=O)N
Properties
Chemical formula	C2H4ClNO
Molar mass	93.51 g·mol^−1
Appearance	Colorless or yellow crystals
Melting point	120 °C (248 °F; 393 K)
Solubility in water	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

• Acetamide
• Iodoacetamide

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. "DECISION du 14 juin 2012" (PDF) (in French). Agence Nationale de Sécurité du Médicament et des Produits de Santé. Cite journal requires |journal= (help)