Chloroacetamide

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
CAS Number	79-07-2 Y
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 Y
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	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)
Solubility in water	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:
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)	[1]
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

Production

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

ClCH₂CO₂CH₃ + NH₃ → ClCH₂C(O)NH₂ + CH₃OH

Uses

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

See also

• Novosphingobium chloroacetimidivorans, a bacterium named after its ability to degrade chloroacetamide