Chloroacetamide

Chloroacetamide
	Structural formula
Names
	Preferred IUPAC name 2-Chloroacetamide
Identifiers
CAS Number	79-07-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:234507;
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 crystals or white fine powder (yellow if impure)
Odor	Characteristic
Density	1.58 g/cm3 at 20 °C
Melting point	120 °C (248 °F; 393 K)
Solubility in water	52.5 g/l at 20 °C; 90 g/L at 25 °C;
Vapor pressure	0.07 hPa at 20 °C
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Very toxic. It is suspected of reproductive toxicity and teratogenicity.
Ingestion hazards	Very toxic
Inhalation hazards	Very toxic
Eye hazards	Irritation
Skin hazards	Irritation
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H317, H361, H402
Precautionary statements	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)	138 mg/kg (oral, rat); >2000 mg/kg (skin, rat)
LC50 (median concentration)	19.8 mg/l, 96 h (Carassius auratus (goldfish))
Safety data sheet (SDS)
Related compounds
Related compounds	Fluoroacetamide; Bromoacetamide; Iodoacetamide; Chloroacetic acid; Acetamide; Dichloroacetamide; N-Chlorosuccinimide;
	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. It is a colorless solid although older samples appear yellow. It has a characteristic odor and is readily soluble in water. It has the structure Cl−CH₂−C(=O)−NH₂.

Production

Chloroacetamide is produced by ammonolysis of esters of chloroacetic acid:

ClCH₂CO₂CH₃ + NH₃ → ClCH₂C(O)NH₂ + CH₃OH

Uses

Chloroacetamide has been used as an herbicide, preservative. 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.

References

1 2 3 4 5 Safety Data Sheet - Chloroacetamine, Sigma-Aldrich, 2026-07-08
↑ 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 978-3-527-30673-2.
↑ 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.

[sigmaaldrich-1] 1 2 3 4 5 Safety Data Sheet - Chloroacetamine, Sigma-Aldrich, 2026-07-08

[inchem-2] 2-Chloroacetamide

[Ullmann-3] Koenig, G.; Lohmar, E.; Rupprich, N. "Chloroacetic Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_537. ISBN 978-3-527-30673-2.

[4] Jacobs, W. A.; Heidelberger, M. (1927). "Chloroacetamide". Organic Syntheses. 7: 16. doi:10.15227/orgsyn.007.0016.

[5] Herbicides - Epochem Archived 2008-05-20 at the Wayback Machine

[6] Acetamide, 2-chloro- - Government of Canada Archived 2009-01-31 at the Wayback Machine

[ANSM-7] "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.

Chloroacetamide

Production

Uses

Hazards

See also

References