2,2'-Dibromobiphenyl

Base Information

• Chemical Name: 2,2'-Dibromobiphenyl
• CAS No.: 13029-09-9
• Molecular Formula: C12H8Br2
• Molecular Weight: 312.004
• Hs Code.: 29039990
• European Community (EC) Number: 625-732-3
• NSC Number: 91566
• UNII: GSL06P6P2L
• DSSTox Substance ID: DTXSID5074761
• Nikkaji Number: J81.532B
• Wikidata: Q27279258
• ChEMBL ID: CHEMBL267917
• Mol file: 13029-09-9.mol

Synonyms:2,2'-Dibromobiphenyl;13029-09-9;2,2'-Dibromo-1,1'-biphenyl;1-bromo-2-(2-bromophenyl)benzene;2,2-DIBROMOBIPHENYL;1,1'-Biphenyl, 2,2'-dibromo-;o,o'-Dibromobiphenyl;Biphenyl, 2,2'-dibromo-;2,2/'-Dibromobiphenyl;2,2'-Dibromophenyl;UNII-GSL06P6P2L;GSL06P6P2L;CHEMBL267917;MFCD00093707;NSC 91566;NSC-91566;1,1'-Biphenyl, 2,2'-dibromo- (9CI);NSC91566;2,2'-dibromodiphenyl;Biphenyl,2'-dibromo-;2,2'-Dibromo-biphenyl;2,2\'-Dibromobiphenyl;1, 2,2'-dibromo-;PBB No. 4;NCIOpen2_009916;PBB 4;2,2''''-Dibromo-Biphenyl;SCHEMBL358976;2,2'-Dibromobiphenyl, 97%;DTXSID5074761;AMY3424;PBB 4 (2,2'-Dibromobiphenyl);2,2'-Dibromo-1,1'-biphenyl #;CS-D1699;BBL103887;BDBM50474730;STL557697;AKOS004910067;OL10150;AC-28773;DS-14951;SY030335;D2874;FT-0636777;2,2 inverted exclamation mark -Dibromobiphenyl;A806055;Q27279258;5,5-dibromo-2-phenyl-cyclohexa-1,3-diene2,2'-dibromo-1,1'-biphenyl

Chemical Property of 2,2'-Dibromobiphenyl

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.007-0.27Pa at 20-50℃
• Melting Point: 79-83 °C
• Boiling Point: 332.884 °C at 760 mmHg
• Flash Point: 180.005 °C
• PSA: 0.00000
• Density: 1.668 g/cm³
• LogP: 4.87860
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 311.89723
• Heavy Atom Count: 14
• Complexity: 161

Purity/Quality:

99% ^*data from raw suppliers

2,2''-Dibromobiphenyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi, N
• Hazard Codes: Xi,N,Xn
• Statements: 36/37/38-50/53-22
• Safety Statements: 37/39-26-61-60-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C2=CC=CC=C2Br)Br
• Uses: 2,2'-Dibromobiphenyl is used to produce 5,5-dimethyl-5H-dibenzosilole at the temperature of -78 - 20°C. It will need reagent n-BuLi and solvents diethyl ether, hexane.

Technology Process of 2,2'-Dibromobiphenyl

There total 34 articles about 2,2'-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: 95.0%

(2-bromophenyl)boronic acid (244205-40-1) → 2,2'-dibromobiphenyl (13029-09-9)

Guidance literature:

With copper diacetate; palladium diacetate; In water; dimethyl sulfoxide; at 20 ℃; for 14h;

DOI:10.1021/acs.orglett.1c00479

Reference yield: 91.0%

→ 2,2'-dibromobiphenyl (13029-09-9)

Guidance literature:

With Duroquinone; In diethyl ether; pentane; at 20 ℃; for 3h;

DOI:10.1021/jo0608063

Reference yield: 87.0%

2,3-dibromobenzene (583-53-9) → 2,2'-dibromobiphenyl (13029-09-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 - 25 ℃;

DOI:10.1039/b511208g

upstream raw materials:

biphenyl

1,1'-biphenyl-2,2'-diamine

2’-bromo-[1,1’-biphenyl]-2-amine

2,3-dibromobenzene

Downstream raw materials:

biphenyl

2-Bromobiphenyl

9-Benzylidene-9H-fluorene

5-oxo-5H-5λ⁵-dibenzophosphol-5-ol

Refernces

• 1、 Liu, Xiang-Yang,Tian, Qi-Sheng,Zhao, Danli,Ran, Quan,Liao, Liang-Sheng,Fan, Jian. "9-Silafluorene and 9-germafluorene: Novel platforms for highly efficient red phosphorescent organic light-emitting diodes". . p. 8144 - 8151. Retrieved 2018.
• 2、 Feng, Lin,Wang, Tao,Jia, Hongxing,Huang, Jianmin,Han, Dong,Zhang, Wenzhao,Ding, Honghe,Xu, Qian,Du, Pingwu,Zhu, Junfa. "On-surface synthesis of planar acenesviaregioselective aryl-aryl coupling". . p. 4890 - 4893. Retrieved 2020.
• 3、 Gilman,Gaj. "-". . p. 447,449. Retrieved 1957.
• 4、 Miyake, Yoshihiro,Wu, Mo,Rahman, M. Jalilur,Kuwatani, Yoshiyuki,Iyoda, Masahiko. "Efficient construction of biaryls and macrocyclic cyclophanes via electron-transfer oxidation of Lipshutz cuprates". . p. 6110 - 6117. Retrieved 2006.
• 5、 Mueller, Matthias,Bettinger, Holger F.,Maichle-Moessmer, Caecilia. "BN-phenanthryne: Cyclotetramerization of an 1,2-azaborine derivative". . p. 9380 - 9383,4. Retrieved 2014.
• 6、 Yang, Shuaijun,Chu, Ming,Miao, Qian. "Connecting two phenazines with a four-membered ring: The synthesis, properties and applications of cyclobuta[1,2-: B:3,4- b ′]diphenazines". . p. 3651 - 3657. Retrieved 2018.
• 7、 Minus, Matthew B.,Moor, Sarah R.,Pary, Fathima F.,Nirmani,Chwatko, Malgorzata,Okeke, Brandon,Singleton, Josh E.,Nelson, Toby L.,Lynd, Nathaniel A.,Anslyn, Eric V.. ""benchtop" Biaryl Coupling Using Pd/Cu Cocatalysis: Application to the Synthesis of Conjugated Polymers". supporting information. p. 2873 - 2877. Retrieved 2021/05/05.