96-12-8

Basic information

• Product Name: 1,2-Dibromo-3-chloropropane
• Synonyms: OS 1897(R);NEMAFU;NEMAFUME(R);NEMAGON(R);3-CHLOROPROPYLENE BROMIDE;3-CHLORO-1,2-DIBROMOPROPANE;1-CHLORO-2 3-DIBROMOPROPANE;1,2-DIBROMOPROPYL CHLORIDE
• CAS NO: 96-12-8
• Molecular Formula: C₃H₅Br₂Cl
• Molecular Weight: 236.33
• EINECS: 202-479-3
• Product Categories: Pharmaceutical Raw Materials;Analytical Chemistry;Chlorinated Compounds (Environmental Endocrine Disruptors);Environmental Endocrine Disruptors;Standard Solution of Volatile Organic Compounds for Water & Soil Analysis;Standard Solutions (VOC);BromoChemical Class;ChloroVolatiles/ Semivolatiles;DIA - DICPesticides;Alpha Sort;BromoVolatiles/ Semivolatiles;Chemical Class;D;DAlphabetic;DIA - DICPesticides&Metabolites;Fungicides;Halogenated;NematicidesPesticides;Others;Pesticides
• Mol File: 96-12-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 6°C
• Boiling Point: 195°C
• Flash Point: 77 °C
• Appearance: /Dense Liquid
• Density: 2.05
• Vapor Pressure: 0.503mmHg at 25°C
• Refractive Index: n/D 1.5542
• Storage Temp.: Refrigerator
• Solubility: Miscible with oils, dichloropropane, and isopropanol (Windholz et al., 1983)
• Water Solubility: 0.123 g/100 mL
• Stability: Stable. Flammable. Incompatible with strong oxidizing agents, chemically active metals and their alloys. May attack some rubber-
• Merck: 14,3020
• BRN: 1732077
• CAS DataBase Reference: 1,2-Dibromo-3-chloropropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Dibromo-3-chloropropane(96-12-8)
• EPA Substance Registry System: 1,2-Dibromo-3-chloropropane(96-12-8)

Safety Data

• Hazard Codes: T,F
• Statements: 45-46-60-25-48/20/22-52/53-39/23/24/25-23/24/25-11
• Safety Statements: 53-45-61-36/37-16-7
• RIDADR: 2872
• WGK Germany: 3
• RTECS: TX8750000
• TSCA: T
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 96-12-8(Hazardous Substances Data)

Usage

Chemical Properties

colourless to slightly yellow liquid

Physical properties

Colorless when pure, however, technical grades are yellowish to dark brown. Pungent odor at high concentrations

Uses

Different sources of media describe the Uses of 96-12-8 differently. You can refer to the following data:
1. Soil fumigant, nematocide and pesticide
2. Formerly as an agricultural nematocide (use banned in the US in 1977)
3. Soil fumigant; nematocide; intermediate in organic synthesis.

Production Methods

DBCP is produced by liquid phase addition of bromine to allyl chloride. It was first produced commercially in the United States in 1955.

General Description

A 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 Reactions

Flammable. Soluble in water. Hydrolyzed in alkali.

Reactivity Profile

1,2-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.

Agricultural Uses

Nematicide, 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 name

BBC 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 Profile

Confirmed 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.

Carcinogenicity

1,2-Dibromo-3-chloropropane is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity fromstudies in experimental animals.

Environmental Fate

Biological. 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).

Toxicity evaluation

DBCP in soil can volatilize from near-surface soil. Based on estimated Koc values of 149 in Lincoln fine sand and 128 in an unspecified soil, DBCP will be highly mobile in soil and has the capacity to leach into groundwater. It is estimated that the volatilization half-life for this chemical will vary between 0.6 days in dry soil with low soil organic content and 26.2 days in a wet soil containing high values of soil organic content. It is important to notice that fields treated with DBCP will present a significant retardation in the volatilization loss from the soil if plastic coverings are used.DBCP will exist primarily in the vapor phase in the ambient atmosphere. It is expected that very small amounts of this chemical will be present in the particulate phase, and this could explain the fact that dry deposition to the earth’s surface will not result in a significant removal process. DBCP presents high water solubility, and then small amounts present in the air can be removed by wet deposition.If found in water, DBCP will volatilize quite rapidly to the atmosphere; the estimated volatilization half-life from a pond is 8 days. Using again the estimated Koc values of 128–149, this chemical is not expected to adsorb significantly to sediment and suspended organic matter. Based on an estimated bioconcentration factor (BCF) of 11.2, it is not expected to bioconcentrate in fish and other aquatic organisms. There is no sufficient data to indicate that DBCP could be a potential risk in terms of biomagnifications in different aquatic or terrestrial food chains. However, some biodegradation of DBCP in groundwater might ensue under anaerobic conditions.

InChI:InChI=1/C3H5Br2Cl/c4-1-3(5)2-6/h3H,1-2H2

Upstream product

• 107-05-1 3-chloroprop-1-ene 
• 3712-44-5 2,2,2-tribromo-1,3,2-benzodioxaphosphole 
• 106-89-8 epichlorohydrin 

Downstream Products

• 50-00-0 formaldehyd 
• 71-52-3 hydrogen carbonate 
• 16400-63-8 2-bromo-3-chloro-propene 
• 85576-83-6 2-Bromo-3-hydroxy-propionaldehyde 
• 513-31-5 2-bromoallyl bromide 
• 10035-10-6 hydrogen bromide 
• 56-81-5 glycerol 

Relevant articles and documents

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Reaction of ortho-Phenylenedioxytrihalophosphoranes with Epichlorohydrin

Dynamic 31P NMR spectroscopy was applied to investigate the reactions of o-phenylenedioxytrihalophosphoranes and bis(o-phenylenedioxy)halophosphoranes with epichlorohydrin as a function of the reagent ratio. α-Opening of the epoxide ring predominantly occurs. With excess epichlorohydrin the reaction with o-phenylenedioxytrichlorophosphorane results in formation of pentaalkoxyphosphorane, while in the reaction with o-phenylenedioxytechintribromophosphorane a mixture of phosphate and pentaalkoxyphosphorane is formed.

REACTIONS OF HALOGEN FLUORIDES. VII. FLUORINATION OF UNSATURATED COMPOUNDS WITH BROMINE TRIFLUORIDE AND AN EQUIMOLAR MIXTURE OF BROMINE TRIFLUORIDE WITH MOLECULAR BROMINE

The reactions of bromine trifluoride and an equimolar mixture of bromine trifluoride and bromine with halogen-substituted alkenes and methyl α-substituted acrylates were investigated.With sufficient dilution of the substrate by Freon 113 (20-25:1) it is possible to obtain the bromofluoro and difluoro adducts with good yiels.The best results (overall yields of fluorination products 80-83percent) were obtained with alkenes containing a halogen at the multiple bond; in the case of more reactive substrates the reaction becomes nonpreparative.The bromofluorination of E- and Z-1,2-dichloroethylenes and E- and Z-1,3-dichloropropenes with pure bromine trifluoride is antistereospecific.The bromofluorination of E- and Z-1,2-dichloroethylenes by the BrF3-Br2 system gives a mixture of diastereomeric bromofluoro adducts as a result of isomerization of the initial olefins in the presence of the bromine.The formation of the difluorides of the halogenated olefins is nonstereospecific and is accompanied by migration of the halogens.