124-48-1

Usage

Uses

1. Used in Fire Extinguisher Fluids, Spray Can Propellants, Refrigerator Fluids, and Pesticides:
CHLORODIBROMOMETHANE was historically used as a component in the production of fire extinguisher fluids, spray can propellants, refrigerator fluids, and pesticides. However, only small amounts are currently produced for laboratory use.
2. Used as Chain Transfer Agents in PVC Polymerization:
In the chemical industry, CHLORODIBROMOMETHANE is utilized as chain transfer agents in the polymerization process of Polyvinyl Chloride (PVC), contributing to the production of this widely used plastic material.
3. Used as a Chemical Reagent/Intermediate in Organic Synthesis:
CHLORODIBROMOMETHANE serves as a valuable chemical reagent and intermediate in various organic synthesis processes, enabling the creation of a range of chemical compounds and products.
4. Used in Water Treatment:
A volatile halogenated methane, CHLORODIBROMOMETHANE is present in trace amounts in drinking water as a result of the water treatment process, playing a role in the overall safety and quality of the water supply.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

CHLORODIBROMOMETHANE is incompatible with strong bases, strong oxidizing agents and magnesium

Health Hazard

Chlorodibromomethane is a central nervous system (CNS) depressant at extremely high concentrations; it is toxic to the liver and kidneys of rodents and induces hepatocellular tumors in mice after long-term exposure. In animal studies, the oral LD50 typically ranges between 800 and 1200 mg/kg.1,2 Acute signs of intoxication include sedation, flaccid muscle tone, ataxia, and prostration; death is due to CNS depression. In cases in which death does not occur until several days after acute exposure, hepatic and renal injury may be the cause of death.

Fire Hazard

CHLORODIBROMOMETHANE is probably combustible.

Safety Profile

Moderately toxic by ingestion. Questionable carcinogen with experimental carcinogenic data. Human mutation data reported. Compounds of this type are generally irritating and narcotic. See also BROMOFORM and CHLOROFORM. When heated to decomposition it emits toxic fumes of Cland Br-.

Potential Exposure

Dibromochloromethane is used as a chemical intermediate in the manufacture of fire extinguishing agents; aerosol propellants; refrigerants, and pesticides. Dibromochloromethane has been detected in drinking water in the United States. It is believed to be formed by the haloform reaction that may occur during

Environmental fate

Biological. Dibromochloromethane showed significant degradation with gradual adaptation in a static-culture flask-screening test (settled domestic wastewater inoculum) conducted at 25 °C. At concentrations of 5 and 10 mg/L, percent losses after 4 wk of incubation were 39 and 25, respectively. At a substrate concentration of 5 mg/L, 16% was lost due to volatilization after 10 d (Tabak et al., 1981). Surface Water. The estimated volatilization half-life of dibromochloromethane from rivers and streams is 45.9 h (Kaczmar et al., 1984). Photolytic. Water containing 2,000 ng/μL of dibromochloromethane and colloidal platinum catalyst was irradiated with UV light. After 20 h, dibromochloromethane degraded to 80 ng/μL bromochloromethane, 22 ng/μL methyl chloride, and 1,050 ng/μL methane. A duplicate experiment was performed but 1 g zinc was added. After about 1 h, total degradation was achieved. Presumed transformation products include methane, bromide, and chloride ions (Wang and Tan, 1988). Chemical/Physical. The estimated hydrolysis half-life in water at 25 °C and pH 7 is 274 yr (Mabey and Mill, 1978). Hydrogen gas was bubbled in an aqueous solution containing 18.8 μmol dibromochloromethane. After 24 h, only 18% of the dibromochloromethane reacted to form methane and minor traces of ethane. In the presence of colloidal platinum catalyst, the reaction proceeded at a much faster rate forming the same end products (Wang et al., 1988).

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo- sions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, and magnesium.

Waste Disposal

May be destroyed by high- temperature incinerator equipped with an HCl scrubber.

InChI:InChI=1/CHBr2Cl/c2-1(3)4/h1H

Upstream product

• 74-87-3 methylene chloride 
• 34557-54-5 methane 
• 67-66-3 chloroform 
• 75-25-2 Bromoform 
• 30957-55-2 1,1-dibromo-1-chloro-propan-2-one 
• 820-10-0 DL-methionine sulfone 
• 16887-00-6 chloride 
• 504-15-4 orcinol 
• 106-44-5 p-cresol 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 496-73-1 4-methyl resorcinol 
• 89-86-1 4-hydroxysalicylic acid 
• 95-71-6 2-methylbenzene-1,4-diol 
• 99-10-5 3,5-Dihydroxybenzoic acid 

Downstream Products

• 593-98-6 1-chloro-1-fluoro-1-bromomethane 
• 34970-00-8 bromochloroiodomethane 
• 22985-29-1 1-bromo-1-chloro-2-phenylcyclopropane 
• 64859-22-9 trans-3-Brom-3-chlor-1,2-diphenyl-cyclopropan 
• 950-79-8 β-Chlor-β-brom-α,α-diphenylethylen 
• 65325-81-7 (2-Bromo-2-chloro-1-methyl-cyclopropyl)-benzene 
• 119-64-2 tetralin 
• 83692-63-1 cis-tricyclo<5.4.0.0^1,3>undec-4-en-6-one 
• 83692-71-1 7-hydroxybicyclo<5.4.0>undec-9-en-2-one 
• 83692-64-2 syn-6-chloromethylenecyclodec-3-enone 
• 83692-62-0 syn-11-chloro-1,6-dihydroxybicyclo<4.4.1>undec-3-ene 
• 83692-68-6 cis-bicyclo<4.4.0>dec-3-ene-1-carboxylic acid 
• 83692-67-5 anti-11-chlorobicyclo<4.4.1>undeca-1,3-dien-6-ol 
• 83692-66-4 anti-6-chloromethylenecyclodec-3-enone 

Related news

Regular articleToxicity and carcinogenicity of CHLORODIBROMOMETHANE (cas 124-48-1) in Fischer 344/N rats and B6C3F1 mice☆09/24/2019

Chlorodibromomethane, a trihalomethane found in water supplies after chlorination, was administered by gavage in corn oil to male and female Fischer 344/N rats and B6C3F1 mice in toxicity studies of 13 weeks and 2 years duration. Doses used in the 13-week study were 0, 15, 30, 60, 125, and 250 m...detailed

Distributions and sea-to-air fluxes of chloroform, trichloroethylene, tetrachloroethylene, CHLORODIBROMOMETHANE (cas 124-48-1) and bromoform in the Yellow Sea and the East China Sea during spring09/09/2019

Halocarbons including chloroform (CHCl3), trichloroethylene (C2HCl3), tetrachloroethylene (C2Cl4), chlorodibromomethane (CHBr2Cl) and bromoform (CHBr3) were measured in the Yellow Sea (YS) and the East China Sea (ECS) during spring 2011. The influences of chlorophyll a, salinity and nutrients on...detailed

Relevant academic research and scientific papers

Brominated-trihalomethane formation from phenolic derivatives as a model of humic materials by the reaction with hypochlorite and hypobromite ions

Among the 21 phenolic derivatives tested for the model system of the disinfection process in the natural water containing humic acid, 2-hydroxytoluene and 2,6-dihydroxybenzoic acid produced high yields of CHBr3 under the co-existence of NaOCl and NaOBr. In the study of distribution of THMs produced, the amount of CHBr3 increased with the relative concentration of NaOCl added to NaOBr. These results were similar to the case of halogenation of the humic acid under the co-existence of NaOCl and NaOBr.

Fe3O4-Catalyzed Halogen-Exchange Reactions of Polyhalomethanes

Triiron tetraoxide pretreated by polyhalomethane was shown to catalyze the halogen-exchange reaction of polyhalomethanes CHlBrmCln (l=1 or 2).The exchange proceeds consecutively giving, for example, CHBrCl2, CHBr2Cl, and C

Chemistry of the biosynthesis of halogenated methanes: C1-organohalogens as pre-industrial chemical stressors in the environment?

We have chemical evidence that in the biosynthesis of the halomethanes C1H(4-n),X(n) (n = 1-4) three different pathways of biogenic formation have to be distinguished. The formation of methyl chloride, methyl bromide, and methyl iodide, respectively, has to be considered as a methylation of the respective halide ions. The dihalo- and trihalomethanes are formed via the haloform and/or via the sulfo-haloform reaction. The possible formation of tetrahalomethanes may involve a radical mechanism. Methionine methyl sulfonium chloride used as substrate in the incubation together with chloroperoxidase (CPO) and H2O2 gave high yields of monohalomethanes only. We were able to show that next to the CPO/H2O2 driven haloform reaction of carbonyl activated methyl groups also methyl-sulphur compounds - e.g. dimethylsulfoxide, dimethylsulfone, and the sulphur amino acid methionine - can act as precursors for the biosynthesis of di- and trihalogenated methanes. Moreover, there is some but not yet very conclusive evidence for an enzymatic production of tetrahalogenated methanes. In our experiments with chloroperoxidase involving amino acids and complex natural peptide based substrates, dihalogenated acetonitriles and several other volatile halogenated but yet unidentified compounds were formed. On the basis of these experiments we like to suggest that biosynthesis of halogenated nitriles occurs in general and therefore a natural atmospheric background should exist for halogenated acetonitriles and halogenated acetaldehydes, respectively.

Brominated trihalomethane formation in halogenation of humic acid in the coexistence of hypochlorite and hypobromite ions

Brominated trihalomethanes (Br-THMs) such as CHCl2Br, CHClBr2, and CHBr3 are produced by the reaction of hypobromite with humic acid in the presence of hypochlorite. In the presence of excess NaOCl, addition of NaOBr enhanced the formation of Br-THMs but reduced the formation of CHCl3. The product distribution of THMs was affected by the ratio of [NaOBr]/[NaOCl] and was independent of pH and reaction time. In the presence of excess NaOBr, the yield of CHBr3 only increased linearly with the NaOCl concentration added. However, the other three THMs were hardly produced even though NaOCl concentration was increased up to 0.5 of the [NaOCl]/[NaOBr] molar ratio. Our results suggest that in the process of THM formation, hypochlorite ion reacts effectively with humic acid in the oxidation reaction and hypobromous acid plays a predominant role in the electrophilic substitution when both of hypohalites are present. Brominated trihalomethanes (Br-THMs) such as CHCl2Br, CHClBr2, and CHBr3 are produced by the reaction of hypobromite with humic acid in the presence of hypochlorite. In the presence of excess NaOCl, addition of NaOBr enhanced the formation of Br-THMs but reduced the formation of CHCl3. The product distribution of THMs was affected by the ratio of [NaOBr]/[NaOCl] and was independent of pH and reaction time. In the presence of excess NaOBr, the yield of CHBr3 only increased linearly with the NaOCl concentration added. However, the other three THMs were hardly-produced even though NaOCl concentration was increased up to 0.5 of the [NaOCl]/[NaOBr] molar ratio. Our results suggest that in the process of THM formation, hypochlorite ion reacts effectively with humic acid in the oxidation reaction and hypobromous acid plays a predominant role in the electrophilic substitution when both of hypohalites are present.

Effects of bromide on the formation of THMs and HAAs

The role of bromide in the formation and speciation of disinfection by-products (DBPs) during chlorination was investigated. The molar ratio of applied chlorine to bromide is an important factor in the formation and speciation of trihalomethanes (THMs) and halogenacetic acids (HAAs). A good relationship exists between the molar fractions of THMs and the bromide incorporation factor. The halogen substitution ability of HOBr and HOCl during the formation of THMs and HAAs can be determined based on probability theory. The formation of HAAs, and their respective concentrations, can also be estimated through use of the developed model.

Facile halogen exchange reactions: Chloroform with bromoform and carbon tetrachloride with carbon tetrabromide

Both of the title systems undergo rapid halogen exchange (half-life ca. 1-2 min) in N-methylpyrolidinone with catalytic sodium hydroxide at room temperature. Yet they differ markedly in response to added p-dinitrobenzene. The rate of the haloform exchange is unaffected, whereas the rate of the carbon tetrahalide exchange is severely retarded. The known base-induced halogen exchange reaction between chloroform and bromoform is shown not to proceed through a reversible carbene intermediate as claimed in the literature. It appears to be best described in terms of the so-called RARP mechanism (radical anion-radical pair). The mechanism proposed for the rapid exchange between carbon tetrachloride and carbon tetrabromide is initial electron transfer, halide ion loss, and ensuing radical chain scrambling of halogen atoms. The acronym RARC, standing for radical anion-radical chain, is proposed.

Modelling the formation of brominated trihalomethanes in chlorinated drinking waters

The chlorination of water containing bromide and natural organic matter (NOM) leads to the formation of brominated trihalomethanes (THMs). The extent of brominated THM formation depends, inter alia, on the bromide:chlorine concentration ratio ([Br-]:[chlorine]). A reaction scheme is proposed from which a simple kinetic model is developed that mathematically relates the extent of bromination, and the relative abundances of the four THMs, to the [Br-]:[chlorine] ratio. In the scheme, the trihalogenated precursors to THMs are formed by three steps each of which substitutes either bromine or chlorine into an activated carbon site in the NOM. This leads to six pairs of competing bromination:chlorination reactions, whose rate constant ratios (k(b):k(c)) have been estimated by using the model to fit THM data obtained from the chlorination of 17 waters from New Zealand. The individual k(b):k(c) ratios range from 4 to 15. From a plot of the ratio of total bromine to total chlorine present in the THMs as a function of the [Br-]:[chlorine] ratio, an apparent overall k(b):k(c) ratio of 9.1 is obtained. Using USEPA cancer potency factors, the model is used to predict the relative cancer risk associated with THMs as a function of the [Br-]:[chlorine] ratio. This risk increases steeply to a peak at a [Br-]:[chlorine] ratio of approximately 0.15, then gradually decreases to the value associated with bromoform alone. The risk associated with THMs may vary considerably through changes in the [Br-]:[chlorine] ratio as the result of natural variation in the [Br-], or through poor control of chlorine dosing.

MANUFACTURE OF DICHLOROPROPANOL

Manufacture of dichloropropanol Process for manufacturing dichloropropa nol wherein a glycerol-based product comprising at least one diol containi ng at least 3 carbon atoms other than 1,2- propanediol, is reacted with a chlorinati ng agent, and of products derived from dichloropropanol such as ep ichlorohydrin and epoxy resins. No figure.

Fluoride anion catalyzed halogen dance in polyhalomethanes

Tetrabutylammonium fluoride catalyzes the exchange of halogens between tetrahalomethanes.The presence of small amounts of haloform is suspected to be a necessary co-catalyst.Key Words: tetrabutyl ammonium fluoride; tetrahalomethanes; halogen exchange in.

Specific Catalyst Effects on Halogen-Exchange Processes with Mixed Dihalogenocarbenes

An improved preparation of chlorodiiodomethane and dibromochloromethane by phase-transfer catalysis is described.Bromochlorocarbene is generated from HCBr2Cl highly selectively (>=97percent) only if tetramethylammonium chloride, dibenzo-18-crown-6, its 3,3',5,5'-tetra-tert-butyl derivative, or 3',5'-di-tert-butylbenzo-15-crown-5 are catalysts.Other investigated catalysts promote extensive halide exchange whereby olefin adducts of dibromo- and dichlorocarbene are formed additionally.