1,2-ジブロモ-3-クロロプロパン

外観

無色～わずかにうすい褐色、液体

溶解性

水に難溶 (0.1g/100ml), DMSO : ≧100mg/ml (20度), 95%エタノール : ≧100mg/ml, メタノール : 易溶, アセトン : ≧100mg/ml, トルエン : 不溶。アセトンに溶ける。

用途

土壌燻蒸剤、殺線虫剤

化学的特性

colourless to slightly yellow liquid

物理的性質

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

使用

Soil fumigant; nematocide; intermediate in organic synthesis.

調製方法

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

一般的な説明

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.

空気と水の反応

Flammable. Soluble in water. Hydrolyzed in alkali.

反応プロフィール

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.

健康ハザード

Inhalation 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.

火災危険

Some of these materials may burn, but none ignite readily. Containers may explode when heated.

农业用途

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.

製品名

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®

安全性プロファイル

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.

発がん性

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

環境運命予測

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).