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3-Bromobiphenyl

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3-Bromobiphenyl Basic information
Description synthesis
Product Name:3-Bromobiphenyl
Synonyms:3-BROMODIPHENYL;3-BROMOBIPHENYL;BROMOBIPHENYL(3-);PBB NO 2;1,1’-(biphenyl,3-bromo-;1,1’-biphenyl,3-bromo-(3-bromobiphenyl);3-bromo-1’-biphenyl;3-bromo-bipheny
CAS:2113-57-7
MF:C12H9Br
MW:233.1
EINECS:218-304-9
Product Categories:Biphenyl derivatives;Biphenyl & Diphenyl ether;Aryl;C9 to C12;Halogenated Hydrocarbons;bc0001
Mol File:2113-57-7.mol
3-Bromobiphenyl Structure
3-Bromobiphenyl Chemical Properties
Melting point 93-94 °C
Boiling point 300 °C
density 1.398 g/mL at 25 °C(lit.)
refractive index 1.637-1.641
Fp 110 °C
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Chloroform (Soluble), DMSO (Slightly)
form Liquid
form L
color Light yellow to gray-beige
Water Solubility Insoluble
Merck 14,4188
BRN 2043191
InChIKeyUSYQKCQEVBFJRP-UHFFFAOYSA-N
CAS DataBase Reference2113-57-7(CAS DataBase Reference)
NIST Chemistry Reference1,1'-Biphenyl, 3-bromo-(2113-57-7)
EPA Substance Registry System3-Bromobiphenyl (2113-57-7)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 37/39-26-36
WGK Germany 3
RTECS DV1750000
TSCA Yes
HS Code 29039990
Toxicitymouse,LDLo,intraperitoneal,500mg/kg (500mg/kg),"Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 6, Pg. 217, 1954.
MSDS Information
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3-Bromobiphenyl English
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3-Bromobiphenyl Usage And Synthesis
Description3-Bromobiphenyl is an important industrial raw material, but also a very widely used organic synthesis intermediates, it is widely used in pharmaceutical, liquid crystal industry and other fields. In recent years, the export volume of 3-Bromobiphenyl in our country is increasing day by day, the main export object is some liquid crystal display production enterprises in Japan and South Korea.
synthesisAdd 1-bromo-3-iodobenzene (4.67 g, 16.5mmol), phenylboronic acid (1.83 g, 15.0 mmol), Pd (OAc)2 (101 mg, 0.450 mmol), PPh3 (239 mg, 0.911 mmol), and K2CO3 (6.23 g, 45.1 mmol) to a 200 mL twonecked round-bottom flask. Add toluene (40 mL) and water (40 mL) via syringe and reflux the mixture (bath temp. 100°C) for 24 h. Extract the resulting mixture with ethyl acetate (30 mL x 3). Dry the combined organic layer over Na2SO4 and concentrate in vacuo. Purify the residue to silica gel column chromatography (eluent:hexane).
Chemical PropertiesColorless to pale yellow liquid
Uses3-Bromobiphenyl is utilized as an electrochemical immunosensor based on poly(dopamine) coated gold nanocluster for brominated flame retardants.
DefinitionT3DB: 3-Monobromobiphenyl is a polybrominated biphenyl. Polybrominated biphenyls (PBBs) are a group of 209 synthetic organic compounds with 1-10 bromine atoms attached to biphenyl. They can be used as flame retardants and may be added to the plastics used to make products like computer monitors, televisions, textiles, and plastic foams to make them difficult to burn. However, the use of PBBs is banned or restricted in most areas due to their toxicity and persistence in the environment.
Synthesis Reference(s)The Journal of Organic Chemistry, 41, p. 24, 1976 DOI: 10.1021/jo00863a005
General DescriptionClear yellow viscous liquid. Insoluble in water.
Air & Water ReactionsInsoluble in water.
Reactivity Profile3-Bromobiphenyl may be sensitive to light. 3-Bromobiphenyl may react with oxidizing materials.
Fire HazardFlash point data for 3-Bromobiphenyl are not available. 3-Bromobiphenyl is probably combustible.
ToxicologyThe exact mechanism of toxicty of PBBs varies depending on the specific congener. The predominant interaction is believed to involve the aryl hydrocarbon receptor (AhR). PBBs bind to and activate the AhR, which in turn initiates the transcriptional upregulation of a number of genes, affecting biochemical and endocrine pathways, cell cycle regulation, morphogenesis, oxidative stress response, and various other processes. This results in the numerous toxic responses characteristic of PBBs. Some of the known induced genes include the cytochrome P-450-dependent monooxygenases CYP1A1 and CYP1A2.
Research3-Bromobiphenyl could be prepared by irradiation of 3,4-dibromobiphenyl (BpBr2) in acetonitrile. At present, a variety of detection methods have been developed to detect its concentration. Such as the electrochemical immunoassay of 3-BBP based on the PDOP/PB/CMK-3 platform and the multi-HRP–DHCNTs–Ab2 signal label. This detection method can detect the concentration of 3-Bromobiphenyl in the environment (This study takes river water from the estuary of the Pearl River as sample solvent)[1-2].
References[1] Sun Z, et al. Electrochemical immunosensor based on hydrophilic polydopamine-coated prussian blue-mesoporous carbon for the rapid screening of 3-bromobiphenyl. Biosensors and Bioelectronics, 2014; 59: 99-105.
[2] Peter K, et al.The photochemistry of polyhaloarenes XIII. The photohydrodehalogenation of 3,4-dibromobiphenyl. Tetrahedron, 1996; 52: 8397-8406.
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