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Chloroacetamide

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Chloroacetamide
Names
Preferred IUPAC name 2-Chloroacetamide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.068 Edit this at Wikidata
EC Number
  • 201-174-2
PubChem CID
UNII
CompTox Dashboard (EPA)
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 ClCH2CONH2
Molar mass 93.51 g·mol
Appearance Colorless crystals or white fine powder (yellow if impure)
Odor Characteristic
Density 1.58 g/cm 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 GHS06: ToxicGHS08: Health hazard
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. 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.

See also

References

  1. ^ 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.
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