2,3-Dibromobiphenyl

Base Information

• Chemical Name: 2,3-Dibromobiphenyl
• CAS No.: 115245-06-2
• Molecular Formula: C₁₂H₈Br₂
• Molecular Weight: 312.004
• UNII: 11P5K461B2
• DSSTox Substance ID: DTXSID80921663
• Nikkaji Number: J105.868A
• Wikidata: Q27251331
• Mol file: 115245-06-2.mol

Synonyms:2,3-Dibromobiphenyl;2,3-Dibromo-1,1'-biphenyl;1,1'-Biphenyl, dibromo-;115245-06-2;1,1'-Biphenyl, 2,3-dibromo-;Dibromo-1,1'-biphenyl;UNII-LK7Y8OHE67;UNII-11P5K461B2;11P5K461B2;27479-65-8;biphenyl dibromide;LK7Y8OHE67;PBB 5;SCHEMBL1627501;DTXSID80921663;Q27251331

Chemical Property of 2,3-Dibromobiphenyl

Chemical Property:

• Vapor Pressure: 0.0002mmHg at 25°C
• Refractive Index: 1.625
• Boiling Point: 337.9°Cat760mmHg
• Flash Point: 183.7°C
• Density: 1.667g/cm³
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 311.89723
• Heavy Atom Count: 14
• Complexity: 175

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=C(C(=CC=C2)Br)Br

Technology Process of 2,3-Dibromobiphenyl

There total 5 articles about 2,3-Dibromobiphenyl which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

1,2-dibromo-3-iodobenzene (1191934-06-1) + phenylboronic acid (98-80-6) → 2,3-dibromo-biphenyl (115245-06-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In ethanol; water; toluene; for 18h; regioselective reaction; Reflux; Inert atmosphere;

DOI:10.1002/ejoc.201001217

Reference yield:

1,2,3-tribromobenzene (608-21-9) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 1,3-dibromobenzene (108-36-1) + 2,6-dibromo-1,1'-biphenyl (59080-32-9) + 2,3-dibromo-biphenyl (115245-06-2) + 2'-bromo-1,1':3',1'-terphenyl

Guidance literature:

at 25 ℃; for 24h; Irradiation;

DOI:10.1246/bcsj.62.3122

Reference yield:

1-Bromo-3-iodobenzene (591-18-4) → 2,3-dibromo-biphenyl (115245-06-2)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -100 °C / Inert atmosphere

2: N-chloro-succinimide; lithium bromide / methanol / 72 h / 25 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; water; toluene / 18 h / Reflux; Inert atmosphere

With N-chloro-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; lithium bromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; hexane; water; toluene; 3: Suzuki-Miyaura coupling;

DOI:10.1002/ejoc.201001217

upstream raw materials:

1,2,3-tribromobenzene

benzene

1,2-dibromo-3-iodobenzene

phenylboronic acid

Refernces

• 1、 Nakada,Miura,Nishiyama,Higashi,Mori,Hirota,Ishii. "Photoreactions of polyhalobenzenes in benzene. Formation of terphenyls". . p. 3122 - 3126. Retrieved 2007/10/02.