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1,2-Dibromo-3-chloropropane

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1,2-Dibromo-3-chloropropane Basic information
1,2-Dibromo-3-chloropropane Chemical Properties
  • Melting point:6°C
  • Boiling point:195°C
  • Density 2.05
  • vapor pressure 0.8 at 21 °C (quoted, Verschueren, 1983)
  • refractive index n/D 1.5542
  • Flash point:77 °C
  • storage temp. Refrigerator
  • solubility Miscible with oils, dichloropropane, and isopropanol (Windholz et al., 1983)
  • form Dense Liquid
  • Water Solubility 0.123 g/100 mL
  • Merck 14,3020
  • BRN 1732077
  • Henry's Law Constant2.49 x 10-4 atm?m3/mol at 20 °C (approximate - calculated from water solubility and vapor pressure)
  • Exposure limitsOSHA PEL: TWA 1 ppb.
  • Stability:Stable. Flammable. Incompatible with strong oxidizing agents, chemically active metals and their alloys. May attack some rubber-based materials.
  • CAS DataBase Reference96-12-8(CAS DataBase Reference)
  • IARC2B (Vol. 20, Sup 7, 71) 1999
  • NIST Chemistry ReferencePropane, 1,2-dibromo-3-chloro-(96-12-8)
  • EPA Substance Registry System1,2-Dibromo-3-chloropropane (96-12-8)
Safety Information
MSDS
1,2-Dibromo-3-chloropropane Usage And Synthesis
  • Chemical Propertiescolourless to slightly yellow liquid
  • Physical propertiesColorless when pure, however, technical grades are yellowish to dark brown. Pungent odor at high concentrations
  • UsesSoil fumigant, nematocide and pesticide
  • UsesSoil fumigant; nematocide; intermediate in organic synthesis.
  • Production MethodsDBCP is produced by liquid phase addition of bromine to allyl chloride. It was first produced commercially in the United States in 1955.
  • General DescriptionA colorless liquid. Denser than water. Flash point 170°F. Boiling point 195°F. Toxic by ingestion and inhalation. Used as a pesticide and fumigant.
  • Air & Water ReactionsFlammable. Soluble in water. Hydrolyzed in alkali.
  • Reactivity Profile1,2-Dibromo-3-chloropropane reacts with chemically active metals such as aluminum, magnesium, tin and their alloys. 1,2-Dibromo-3-chloropropane will attack some rubber materials and coatings.
  • Health HazardInhalation of vapors or dust is extremely irritating. May cause burning of eyes and flow of tears. May cause coughing, difficult breathing and nausea. Brief exposure effects last only a few minutes. Exposure in an enclosed area may be very harmful. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may cause pollution.
  • Fire HazardSome of these materials may burn, but none ignite readily. Containers may explode when heated.
  • Agricultural UsesNematicide, Fumigant: DBCP has been used in agriculture as a nematicide since 1955, being supplied for such use in the forms of liquid concentrate, emulsifiable concentrate, powder, granules, and solid material. A rebuttable presumption against registration for pesticide uses was issued by U.S. EPA on September 22, 1977, on the basis of oncogenicity and reproductive effects. Then, as of November 3, 1977, EPA in a further action suspended all registrations of end-use products, subject to various specific restrictions. Not listed as registered in EU countries.
  • Trade nameBBC 12®; FUMAGONE®; FUMAZONE®[C]; MEMATOCIDE®; NEMABROM®; NEMAFUM®; NEMAGON®[C]; NEMAGON SOIL FUMIGANT®[C]; NEMANAX®; NEMAPAZ®; NEMASET®; NEMATOCIDE®[C]; NEMATOX®; NEMAZON®; OS 1897®; OXY BCP®[C]; SD 1897®
  • Safety ProfileConfirmed human carcinogen with experimental carcinogenic and teratogenic data. Poison by ingestion, inhalation, and subcutaneous routes. Moderately toxic by skin contact. An eye and severe skin irritant. Narcotic in high concentrations. Has been implicated in causing human sterihty in male factory workers. Human mutation data reported. A soil fumigant. Combustible. When heated to decomposition it emits toxic fumes of Cl and Br-. See also CHLORIDES and BROLVIDES.
  • Carcinogenicity1,2-Dibromo-3-chloropropane is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity fromstudies in experimental animals.
  • Environmental FateBiological. Biodegradation is not expected to be significant in removing 1,2-dibromo- 3-chloropropane. In aerobic soil columns, no degradation was observed after 25 days (Wilson et al., 1981a).
    Soil. Soil water cultures converted 1,2-dibromo-3-chloropropane to n-propanol, bromide and chloride ions. Precursors to the alcohol formation include allyl chloride and allyl alcohol (Castro and Belser, 1968). The reported half-life in soil is 6 months (Jury et al., 1987).
    Groundwater. According to the U.S. EPA (1986) 1,2-dibromo-3-chloropropane has a high potential to leach to groundwater.
    Chemical/Physical. 1,2-Dibromo-3-chloropropane is subject to both neutral and basemediate hydrolysis (Kollig, 1993). Under neutral conditions, the chlorine or bromine atoms may be displaced by hydroxyl ions. If nucleophilic attack occurs at the carbon-chlorine bond, 2,3-dibromopropanol is formed which reacts further to give 2,3-dihydroxybromopropane via the intermediate epibromohydrin. 2,3-Dihydroxybromopropane will undergo hydrolysis via the intermediate 1-hydroxy-2,3-propylene oxide which further reacts with water to give glycerol. If the nucleophilic attack occurs at the carbon-bromine bond, 2- bromo-3-chloropropanol is formed which further reacts forming the end product glycerol (Kollig, 1993). If hydrolysis of 1,2-dibromo-2-chloropropane occurs under basic conditions, the compound will undergo dehydrohalogenation to form 2-bromo-3-chloropropene and 2,3-dibromo-1-propene as intermediates. Both compounds are subject to further attack forming 2-bromo-3-hydroxypropene as the end product (Burlinson et al., 1982; Kollig, 1993). The hydrolysis half-life at pH 7 and 25°C was calculated to be 38 years (Burlinson et al., 1982; Ellington et al., 1986).
    Emits toxic chloride and bromide fumes when heated to decomposition (Lewis, 1990).
1,2-Dibromo-3-chloropropane Preparation Products And Raw materials
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