16606-02-3

Basic information

• Product Name: 2,4',5-TRICHLOROBIPHENYL
• Synonyms: PCB-31;PCB NO 31;BALLSCHMITER NO 31;BZ NO 31;2,4',5-TRICHLOROBIPHENYL;2,4',5-PCB;2,4’,5-trichloro-1’-biphenyl;2,4’,5-trichloro-bipheny
• CAS NO: 16606-02-3
• Molecular Formula: C₁₂H₇Cl₃
• Molecular Weight: 257.54
• Mol File: 16606-02-3.mol

Chemical Properties

• Melting Point: 67℃
• Boiling Point: 334.36°C (rough estimate)
• Appearance: /
• Density: 1.3510 (rough estimate)
• Refractive Index: 1.6040 (rough estimate)
• Water Solubility: 0.11mg/L(22.5 oC)
• CAS DataBase Reference: 2,4',5-TRICHLOROBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4',5-TRICHLOROBIPHENYL(16606-02-3)
• EPA Substance Registry System: 2,4',5-TRICHLOROBIPHENYL(16606-02-3)

Safety Data

• Hazard Codes: N,Xn
• Statements: 33-50/53
• Safety Statements: 35-60-61
• RIDADR: UN 3432 9/PG 2
• RTECS: DV8810000
• Hazardous Substances Data: 16606-02-3(Hazardous Substances Data)

Usage

Safety Profile

Moderately toxic byintraperitoneal route. Experimental reproductive effects.When heated to decomposition it emits toxic vapors ofClí.

Upstream product

• 308817-89-2 2-(4'-aminophenyl)-4-chloroaniline 
• 106-46-7 para-dichlorobenzene 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 94-17-7 bis(4-chlorobenzoyl)peroxide 
• 637-87-6 1-Chloro-4-iodobenzene 
• 29682-41-5 2,5-dichloroiodobenzene 
• 1435-50-3 2-bromo-1,4-dichlorobenzene 
• 1679-18-1 4-Chlorophenylboronic acid 
• 89306-00-3 N,N'-(5-chloro-biphenyl-2,4'-diyl)-bis-acetamide 

Downstream Products

• 34883-43-7 2,4'-dichlorobiphenyl 
• 2974-90-5 3,4'-dichlorobiphenyl 
• 34883-39-1 2,5-dichlorobiphenyl 
• 92-52-4 biphenyl 

Relevant articles and documents

Regularities of Pd/C-catalyzed reduction of trichlorobiphenyls with 2-propanol in basic medium

Reduction of a series of trichlorobiphenyls with 2-propanol in basic medium catalyzed by Pd/C has been studied. Regioselectivity of the reduction has been determined. In the studied cases, the chlorine atom in para or meta positions of the more substituted ring has been more reactive. Using isotope labeling, it has been demonstrated that the reaction occurs via the stage of 2-propanol dehydration on palladium catalyst, followed by catalytic hydrogenation of the polychlorinated biphenyls.

METHOD FOR SEPARATING AND CLEANING UP POLYHALOGENATED BIPHENYLS

The method for separating and cleaning up polyhalogenated biphenyls (PHBs) is characterized by comprising the following three steps: (1) the step of bringing a sample containing PHBs into contact with a fibrous activated carbon; (2) the step of washing the fibrous activated carbon with hexanes; and (3) the step of eluting PHBs from the fibrous activated carbon.

Synthesis of polychlorinated biphenyls and their metabolites with a modified Suzuki-coupling

A modified procedure for the synthesis of polychlorinated biphenyls (PCBs) utilizing the Suzuki-coupling, a palladium-catalyzed cross-coupling reaction, is described. The coupling of (chlorinated) benzene boronic acids with bromochlorobenzenes, using Pd(dppf)2Cl2 (dppf=1,1 ′-bis(diphenylphosphino)ferrocene) as the catalyst and aqueous sodium carbonate as the base, gave the desired PCB congeners in moderate to good yields. Eleven PCB congeners, including environmentally important PCB congeners and metabolites, were synthesized using this modified procedure. This new catalyst Pd(dppf)2Cl2 offers the advantage of being less air-sensitive and has a longer shelf life compared to Pd(PPh4) 4. Three new (di-)methoxylated PCB congeners were synthesized using the same procedure by either coupling a chlorinated benzene boronic acid with a bromo (di-)methoxybenzene or by coupling a (di-)methoxy benzene boronic acid with a chlorinated bromobenzene. The dimethoxylated PCB congeners were readily converted into the respective dihydroxylated PCB derivatives using boron tribromide in dichloromethane. This approach offers the advantage of high selectivity and moderate to good yields compared to conventional methods such as the Cadogan reaction and allows the use of less toxic starting materials.

Photochemical behaviour of 1,4-dichlorobenzene in aqueous solution

Several photoproducts were identified in the direct photolysis of 1,4-dichlorobenzene (1,4-DCB) in air-saturated aqueous solution, namely 4-chlorophenol, hydroquinone, hydroxybenzoquinone, and 2,5-dichlorophenol. In the absence of oxygen the latter is not formed and phenol was detected, but the unexpected formations of 4,4′-dichlorobiphenyl, 2,4′,5-trichlorobiphenyl, and a terphenyl derivative are observed. Mechanisms are proposed to explain the formations of identified photoproducts. The phototransformation of 1,4-DCB may be photoinduced by NO3- or FeIII salts. The main primary product is 2,5-dichlorophenol, which results from a hydroxylation without dechlorination. Some other products have been identified in particular 4-chlorophenol and 2,5-dichlorobenzoquinone in the case of FeIII salts.

Physical, spectral and chromatographic properties of all 209 individual PCB congeners

Through the use of two capillary GC columns: 40% octadecyl/ 15% phenyl methyl siloxane and 50% phenyl methyl siloxane, it was possible to separate 201 PCB congeners with only four unresolved pairs. The data compiled in this study for all 209 congeners will aid in the identification of selected individual components of these environmental pollutants. The use of this data also presents the opportunity for the improved quantification of the commercial PCB formulations. -from Authors

Synthesis of C 14 labeled environment contaminants

Upon the reaction of benzene-14C via nitrobenzene-14C and aniline-14C, some 14C-labelled environmental contaminants were were synthesized. By chlorination of aniline-14C and acetanilide-14C the authors prepared chloroanilines-14C. Gomberg-Bachmann or Cadogan reaction of diazotated chloroanilines-14C with different chlorobenzenes gave di, tri- and pentachlorobiphenyls-14C. By boiling anilinediazonium sulfate-14C the authors prepared phenol-14C, which was chlorinated to give 2,4,6-trichlorophenol-14C. Hexachlorobenzene-14C and pentachloronitrobenzene-14C were prepared by chlorination of nitrobenzene- 14C. Chloralkylene 9-14C was synthesized by Friedel-Crafts alkylation of 2,4'-dichlorobiphenyl-14C with 2-chloropropane.