Chloroacetamide

Chloroacetamide
Names
	Preferred 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
Related compounds
Related compounds	Fluoroacetamide; Bromoacetamide; Iodoacetamide; Chloroacetic acid; Acetamide; Dichloroacetamide;
	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 Cl C H₂CO NH₂. Chloroacetamide is a colorless solid although older samples appear yellow. It has a characteristic odor and is readily soluble in water.^[1]

Production[edit]

Chloroacetamide is produced by ammonolysis of esters of chloroacetic acid:^[2]^[3]

ClCH₂CO₂CH₃ + NH₃ → ClCH₂C(O)NH₂ + CH₃OH

Uses[edit]

Chloroacetamide has been used as an herbicide,^[4] preservative.^[5] and in the manufacturing of pharmaceuticals.

Hazards[edit]

Chloroacetamide is toxic, irritates eyes and skin, and may cause an allergic reaction. It is suspected of reproductive toxicity and teratogenicity.^[6]

References[edit]

^ 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.

[inchem-1] 2-Chloroacetamide

[Ullmann-2] 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.

[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

[ANSM-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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[2]

[3]

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[5]

[6]

Production[edit]

Uses[edit]

Hazards[edit]

See also[edit]

References[edit]