Chloroacetamide (2-chloroacetamide) is a chlorinated organic compound with the molecular formula ClCH2CONH2. It is a colorless solid although older samples appear yellow. It has a characteristic odor and is readily soluble in water.[2] It has the structure Cl−CH2−C(=O)−NH2.

Chloroacetamide
Names
Preferred IUPAC name
2-Chloroacetamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.068 Edit this at Wikidata
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
ClCH2CONH2
Molar mass 93.51 g·mol−1
Appearance Colorless crystals or white fine powder[1] (yellow if impure)
Odor Characteristic
Density 1.58 g/cm3 at 20 °C[1]
Melting point 120 °C (248 °F; 393 K)
  • 52.5 g/l at 20 °C[1]
  • 90 g/L at 25 °C
Vapor pressure 0.07 hPa at 20 °C[1]
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:
GHS06: ToxicGHS08: Health hazard
Danger
H301, H317, H361, H402
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):
138 mg/kg (oral, rat)
>2000 mg/kg (skin, rat)
19.8 mg/l, 96 h (Carassius auratus (goldfish))
Safety data sheet (SDS) [1]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Production

edit

Chloroacetamide is produced by ammonolysis of esters of chloroacetic acid:[3][4]

ClCH2CO2CH3 + NH3 → ClCH2C(O)NH2 + CH3OH

Uses

edit

Chloroacetamide has been used as an herbicide,[5] preservative.[6] 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.[7]

See also

edit

References

edit
  1. ^ a b c d e https://www.sigmaaldrich.cn/CN/en/sds/mm/8.02412?userType=anonymous
  2. ^ 2-Chloroacetamide
  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 978-3527306732.
  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
  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.