5-Bromo[1,1'-biphenyl]-2-ol

Base Information

• Chemical Name: 5-Bromo[1,1'-biphenyl]-2-ol
• CAS No.: 16434-97-2
• Molecular Formula: C12H9 Br O
• Molecular Weight: 249.107
• Hs Code.: 2907199090
• European Community (EC) Number: 240-490-5
• NSC Number: 95701
• UNII: 3MHV399T7M
• DSSTox Substance ID: DTXSID80167746
• Nikkaji Number: J94.987F
• Wikidata: Q83037187
• Mol file: 16434-97-2.mol

Synonyms:16434-97-2;4-bromo-2-phenylphenol;5-bromo[1,1'-biphenyl]-2-ol;5-Bromo-[1,1'-biphenyl]-2-ol;5-Bromo(1,1'-biphenyl)-2-ol;3MHV399T7M;EINECS 240-490-5;NSC-95701;(1,1'-Biphenyl)-2-ol, 5-bromo-;[1,1'-Biphenyl]-2-ol, 5-bromo-;NSC95701;4-Bromo-2-phenyl phenol;UNII-3MHV399T7M;SCHEMBL7058282;DTXSID80167746;5-BROMO-2-HYDROXYBIPHENYL;5-bromo[1,1/'-biphenyl]-2-ol;NSC 95701;AKOS015958997;E97879

Chemical Property of 5-Bromo[1,1'-biphenyl]-2-ol

Chemical Property:

• Melting Point: 53.35°C
• Refractive Index: 1.6565 (estimate)
• Boiling Point: 327.5°Cat760mmHg
• Flash Point: 151.9°C
• PSA: 20.23000
• Density: 1.471g/cm³
• LogP: 3.82170
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 247.98368
• Heavy Atom Count: 14
• Complexity: 177

Purity/Quality:

99% ^*data from raw suppliers

5-Bromo[1,1'-biphenyl]-2-ol ^*data from reagent 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)O

Technology Process of 5-Bromo[1,1'-biphenyl]-2-ol

There total 8 articles about 5-Bromo[1,1'-biphenyl]-2-ol 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: 94.0%

2-Phenylphenol (90-43-7,287950-96-3) → 5-bromo-[1,1′-biphenyl]-2-ol (16434-97-2)

Guidance literature:

With bis(trichloromethyl) carbonate; tetrabutylammomium bromide; potassium bromide; In water; ethyl acetate; at 20 ℃; for 19h; regioselective reaction;

DOI:10.1016/j.tet.2019.130539

Reference yield: 91.0%

2-Phenylphenol (90-43-7,287950-96-3) → 5-bromo-[1,1′-biphenyl]-2-ol (16434-97-2) + 3-bromo[1,1’-biphenyl]-2-ol (23197-48-0)

Guidance literature:

With N-Bromosuccinimide; at 0 ℃; for 2h; regioselective reaction;

DOI:10.1021/acs.joc.7b02920

Reference yield: 87.0%

2-phenyl-1,3,2-benzodioxaborole (5747-23-9) + 4-bromo-6-diazocyclohexa-2,4-dien-1-one → 5-bromo-[1,1′-biphenyl]-2-ol (16434-97-2)

Guidance literature:

With potassium carbonate; In dichloromethane; acetone; at 55 ℃; for 7h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.202006542

upstream raw materials:

acetic acid-(5-bromo-biphenyl-2-yl ester)

2-Phenylphenol

carbon disulfide

bromine

Downstream raw materials:

acetic acid-(5-bromo-biphenyl-2-yl ester)

Refernces

• 1、 Xu, Yingzhou,Hu, Dufen,Zheng, Hui,Mei, David,Gao, Zhaobo. "Regioselective bromination of arenes mediated by triphosgene-oxidized bromide". supporting information. . Retrieved 2019/08/30.
• 2、 Satkar, Yuvraj,Ramadoss, Velayudham,Nahide, Pradip D.,García-Medina, Ernesto,Juárez-Ornelas, Kevin A.,Alonso-Castro, Angel J.,Chávez-Rivera, Ruben,Jiménez-Halla, J. Oscar C.,Solorio-Alvarado, César R.. "Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: The PIDA-AlBr3 system". . p. 17806 - 17812. Retrieved 2018/05/28.