Chloroacetone

Title: Chloroacetone
CAS Registry Number: 78-95-5
CAS Name: 1-Chloro-2-propanone
Additional Names: chloracetone; monochloroacetone; monochloracetone; acetonyl chloride; chloropropanone; 1-chloro-2-ketopropane; 1-chloro-2-oxopropane
Molecular Formula: C3H5ClO
Molecular Weight: 92.52
Percent Composition: C 38.95%, H 5.45%, Cl 38.32%, O 17.29%
Line Formula: ClCH2COCH3
Literature References: Prepn by the action of chlorine upon diketene: A. B. Boese, Jr., US 2209683 (1940 to Carbide and Carbon Chem.); by chlorination of acetone: E. J. Rahrs, US 2235562 (1941 to Eastman Kodak); G. H. Morey, US 2243484 (1941 to Commercial Solvents Corp.). Stabilization: idem, US 2229651 (1941 to Commercial Solvents Corp.); E. J. Rahrs, US 2263010 (1941 to Eastman Kodak). Forms binary azeotropes with many organic liquids: L. H. Horsley, Azeotropic Data, Advances in Chemistry Series No. 6 (Washington, 1952) p 73. Reacts with aryl Grignard reagents to form stilbenes: Huang, J. Chem. Soc. 1954, 2539. Toxicology: E. V. Sargent et al., Am. Ind. Hyg. Assoc. J. 47, 375 (1986).
Properties: Liquid. Pungent odor. Lacrimator. Turns dark and resinifies on prolonged exposure to light. May be stabilized by addition of 0.1% H2O or 1.0% CaCO3. d425 1.123; d415 1.135. mp -44.5°. bp 119.7°, bp50 61°, bp12 20°. Volatile with steam. Surface tension at 20° = 35.27 dyn/cm. Dipole moment in hexane, 2.36D. Sol in 10 parts water (w/w). Miscible with alcohol, ether, chloroform. LD50 (14 day) in mice, rats (mg/kg): 127, 100 orally; LC50 (1 hr) in rats (ppm): 262 by inhalation (Sargent).
Melting point: mp -44.5°
Boiling point: bp 119.7°; bp50 61°; bp12 20°
Density: d425 1.123; d415 1.135
Toxicity data: LD50 (14 day) in mice, rats (mg/kg): 127, 100 orally; LC50 (1 hr) in rats (ppm): 262 by inhalation (Sargent)
Derivative Type: 2,4-Dinitrophenylhydrazone
Properties: Yellow needles from alc, mp 124°.
Melting point: mp 124°
CAUTION: Intensely irritating to eyes, skin, mucous membranes.
Use: Has been proposed as tear gas component for police and military use; in the manuf of couplers for color photography; as enzyme inactivator; intermediate in the manuf of perfumes, antioxidants, drugs; in insecticide formulations; in photopolymerization of vinyl compds. Proposed as catalyst in tetraethyllead production, as selective solvent for separating diolefins.
Chloroacetyl Isocyanate Chloroaniline Chloroarsenol Chloroazodin Chlorobenzene

Chloroacetone
Chloroacetone 2D skeletal.svg
Chloroacetone-3D-balls.png
Identifiers
CAS number 78-95-5 YesY
PubChem 6571
ChemSpider 6323 YesY
UNII 60ZTR74268 YesY
EC number 201-161-1
ChEBI CHEBI:47220 YesY
RTECS number UC0700000
Jmol-3D images Image 1
Properties
Molecular formula C3H5ClO
Molar mass 92.52 g mol−1
Appearance Colorless liquid, oxidizes to amber
Density 1.123 g/cm3
Melting point −44.5 °C; −48.1 °F; 228.7 K
Boiling point 119 °C; 246 °F; 392 K
Solubility in water 10 g/100 mL at 20 °C
Solubility miscible in alcohol, ether, chloroform
Vapor pressure 1.5 kPa
Dipole moment 2.36
Hazards
Flash point 35 °C; 95 °F; 308 K
Autoignition temperature 610 °C; 1,130 °F; 883 K
Explosive limits 3.4% - ?[1]
LD50 100 mg/kg (rats, oral)[2]
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Chloroacetone is a chemical compound with the formula CH3COCH2Cl. At STP it is a colourless liquid with a pungent odour.[3] On exposure to light, it turns to a dark yellow-amber colour.[4] It was used as a tear gas in World War I.[5]