594-15-0

Basic information

• Product Name: TRIBROMOCHLOROMETHANE
• Synonyms: TRIBROMOCHLOROMETHANE
• CAS NO: 594-15-0
• Molecular Formula: CBr₃Cl
• Molecular Weight: 287.18
• EINECS: 209-827-3
• Mol File: 594-15-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 55°C
• Boiling Point: 104.3°C (estimate)
• Flash Point: 52.8°C
• Appearance: /
• Density: 2.7100
• Vapor Pressure: 3.79mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• CAS DataBase Reference: TRIBROMOCHLOROMETHANE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIBROMOCHLOROMETHANE(594-15-0)
• EPA Substance Registry System: TRIBROMOCHLOROMETHANE(594-15-0)

Safety Data

• Hazardous Substances Data: 594-15-0(Hazardous Substances Data)

Usage

Uses

Tribromochloromethane is a potentially toxic disinfection byproducts generated at water treatment plants in USA.

Purification Methods

wash it with aqueous Na2S2O3, dry it with BaO and fractionally crystallise from its melt. It also crystallises from EtOH and distils at atmospheric pressure. [Beilstein 1 H 68, 1 II 35, 1 III 91, 1 IV 85.]

InChI:InChI=1/CBr3Cl/c2-1(3,4)5

Upstream product

• 67-66-3 chloroform 
• 56-23-5 tetrachloromethane 
• 75-25-2 Bromoform 
• 75-62-7 Bromotrichloromethane 
• 594-18-3 dibromodichloromethane 
• 558-13-4 carbon tetrabromide 
• 73411-13-9 dibromochloronitrosomethane 
• 7726-95-6 bromine 
• 7681-52-9 sodium hypochlorite 
• 10035-10-6 hydrogen bromide 
• 10294-33-4 boron tribromide 
• 7727-15-3 aluminium bromide 

Downstream Products

• 103670-60-6 (1,1-dibromo-3,3,3-trifluoroprop-1-en-2-yl)benzene 
• 56-23-5 tetrachloromethane 
• 75-62-7 Bromotrichloromethane 
• 594-18-3 dibromodichloromethane 
• 558-13-4 carbon tetrabromide 
• 35621-91-1 (Z)-(2-bromo-2-chlorovinyl)benzene 
• 35621-92-2 (E)-(2-bromo-2-chlorovinyl)benzene 
• 7726-95-6 bromine 
• 34902-22-2 Chlordibrommethylradikal 

Relevant articles and documents

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.

Synthesis of fluorinated 1,2,3-butatrienes from α-halovinyl organometallic reagents

The thermal stability and dimerization reaction of fluorinated α-halovinyl zinc and copper reagents, RR'C=CYM (Y = F, Cl, Br; M = ZnX, Cu), have been explored in detail. Dimerization of these vinyl carbenoids to betatrienes occurred when R was an aromatic (C6H5 or C6F5) and R' was a perfluoroalkyl group (CF3, C2F5, C3F7). The role of the α-halogen was determined; the α-F vinyl copper reagent (R = C6H5, R' = CF3) decomposed by oxidative dimerization to 1,3-dienes while the α-Br and -Cl copper reagents dimerized to butatrienes. The fluorinated butatrienes prepared in this study, (E)- and (Z)-R1R2C==C=C=CR1R2 (R1 = CF3, R2 = C6H5; R1 = C2F5, R2 = C6H5; R1 = n-C3F7, R2 = C6H5; R1 = CF3, R2 = C6F5) are available on a multigram scale and readily obtained with high isomeric purity. The geometry of one member of each isomeric pair of butatrienes was characterized by X-ray crystallography. The mechanism of the dimerization reaction has been determined to be a nucleophilic displacement/β-elimination process. Diels-Alder (1,2-addition), bromination (1,2-addition), and isomerizatioa reactions are described.