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Chloroacetone

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Chloroacetone Basic information
Chloroacetone Chemical Properties
  • Melting point:-44.5 °C
  • Boiling point:120 °C (lit.)
  • Density 1.162 g/mL at 25 °C (lit.)
  • vapor pressure 42 hPa (20 °C)
  • refractive index n20/D 1.432(lit.)
  • Flash point:82 °F
  • storage temp. 2-8°C
  • form Liquid
  • color Clear yellow to yellow-brown
  • Specific Gravity1.162
  • PH4.3 (124g/l, H2O, 20°C)
  • explosive limit3.4%(V)
  • Water Solubility 124 g/L (20 ºC)
  • Sensitive Lachrymatory
  • Merck 14,2114
  • BRN 605369
  • Stability:Stable. Incompatible with strong oxidizing agents, strong bases. May discolour on exposure to light. STENCH.
  • CAS DataBase Reference78-95-5(CAS DataBase Reference)
  • NIST Chemistry Reference2-Propanone, 1-chloro-(78-95-5)
  • EPA Substance Registry SystemChloroacetone (78-95-5)
Safety Information
MSDS
Chloroacetone Usage And Synthesis
  • Chemical Propertiescolourless to dark yellow liquid
  • UsesCouplers for color photography, enzyme inactivator, insecticides, perfumes, intermediate, organic synthesis, tear gas, polymerization of vinyl monomers.
  • UsesManufacture of couplers for color photography; intermediate in manufacture of perfumes, antioxidants, drugs, plant growth regulators, defoliants, and herbicides
  • UsesChloroacetone was used in the synthesis of double-chain nonionic surfactants with an acid decomposition function via acid-catalyzed condensation with fatty alcohols (octyl, decyl and dodecyl). It was also used in the synthesis of meso-tetramethyl tetrakis-(4-phenoxy acetone)calix[4]pyrrole. It can also be used to make dye couplers for color photography and used in the Feist-Benary synthesis of furans.
  • DefinitionA lachrymator.
  • Synthesis Reference(s)Journal of the American Chemical Society, 77, p. 5274, 1955 DOI: 10.1021/ja01625a016
    Synthesis, p. 188, 1987 DOI: 10.1055/s-1987-27886
  • General DescriptionA yellow-colored liquid with an irritating pungent odor. Light sensitive, but stabilized with the addition of small amounts of water and/or calcium carbonate. Slightly soluble in water and denser than water. Vapors much heavier than air. Irritates skin and eyes. Very toxic by ingestion or inhalation. Used to make other chemicals. A lachrymator.
  • Air & Water ReactionsHighly flammable. Water soluble.
  • Reactivity ProfileCHLOROACETONE turns dark and resinifies on prolonged exposure to light [Merck]. This occurred in a bottle during storage for two years on a shelf in diffused light. A few days after the bottle was moved, Chloroacetone exploded [Ind. Eng. News 9: 184(1931)]. Is stabilized by addition of 0.1% water or 0.1% CaCO3.
  • HazardStrong irritant to tissue, eyes, and mucous membranes; toxic by ingestion and skin contact. Upper respiratory tract irritant.
  • Health HazardTOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
  • Fire HazardHIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
  • Safety ProfilePoison by inhalation, ingestion, and skin contact. Mutation data reported. A lachrymator poison gas. See also CHLORINATED HYDROCARBONS, ALIPHATIC; ACETONE. Flammable when exposed to heat or flame, or oxidizers. Old material can explode. When heated to decomposition it emits highly toxic fumes.
  • Purification MethodsDissolve it in water and shake it repeatedly with small amounts of diethyl ether which extracts, preferentially, 1,1-dichloroacetone present as an impurity. The chloroacetone is then extracted from the aqueous phase using a large amount of diethyl ether, and distilled at slightly reduced pressure. It is dried with CaCl2 and stored at Dry-ice temperature. Alternatively, it was stood over CaSO4, distilled and stored over CaSO4. It is steam volatile. The 2,4-dinitrophenylhydrazone forms yellow needles from EtOH with m 120o or 124o. [Beilstein 1 IV 3215.] LACHRYMATOR with toxic vapour.
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