4'-Chloro-2-methyl-1,1'-biphenyl

Base Information

• Chemical Name: 4'-Chloro-2-methyl-1,1'-biphenyl
• CAS No.: 89346-57-6
• Molecular Formula: C13H11Cl
• Molecular Weight: 202.683
• DSSTox Substance ID: DTXSID90513492
• Nikkaji Number: J1.331.477B
• Wikidata: Q82373339
• Mol file: 89346-57-6.mol

Synonyms:89346-57-6;1,1'-Biphenyl, 4'-chloro-2-methyl-;4'-Chloro-2-methyl-1,1'-biphenyl;SCHEMBL172733;DTXSID90513492;4-chloro-2'-methyl-1,1'-biphenyl;AKOS004118799;BB 0223574

Chemical Property of 4'-Chloro-2-methyl-1,1'-biphenyl

Chemical Property:

• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 202.0549280
• Heavy Atom Count: 14
• Complexity: 170

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1C2=CC=C(C=C2)Cl

Technology Process of 4'-Chloro-2-methyl-1,1'-biphenyl

There total 10 articles about 4'-Chloro-2-methyl-1,1'-biphenyl 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: 65.0%

bromochlorobenzene (106-39-8) + ortho-tolylmagnesium bromide (932-31-0) → 2,2”-dimethyl-1,1‘:4’,1“-terphenyl (53092-64-1) + 4'-chloro-2-methyl-1,1'-biphenyl (89346-57-6)

Guidance literature:

With nickel dichloride; In tetrahydrofuran; at 50 ℃; for 2h;

DOI:10.1080/00397919108016772

Reference yield:

4-chlorophenyl trifluoromethanesulfonate (29540-84-9) + 2-Methylphenylboronic acid (16419-60-6) → 2,2”-dimethyl-1,1‘:4’,1“-terphenyl (53092-64-1) + 4'-chloro-2-methyl-1,1'-biphenyl (89346-57-6) + 2′-methyl-[1,1′-biphenyl]-4-yl trifluoromethanesulfonate

Guidance literature:

With potassium fluoride; (η³-1-^tBu-indenyl)Pd(SIPr)Cl; water; In tetrahydrofuran; at 25 ℃; for 12h; chemoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.9b01692

Reference yield:

4-chloro-phenol (106-48-9,82344-39-6) → 2,2”-dimethyl-1,1‘:4’,1“-terphenyl (53092-64-1) + 4'-chloro-2-methyl-1,1'-biphenyl (89346-57-6) + 2′-methyl-[1,1′-biphenyl]-4-yl trifluoromethanesulfonate

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 16 h / 0 - 20 °C / Sealed tube; Inert atmosphere

2: (η³-1-^tBu-indenyl)Pd(SIPr)Cl; potassium fluoride; water / tetrahydrofuran / 12 h / 25 °C / Inert atmosphere; Sealed tube

With pyridine; potassium fluoride; (η³-1-^tBu-indenyl)Pd(SIPr)Cl; water; In tetrahydrofuran; dichloromethane; 2: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.joc.9b01692

upstream raw materials:

4-chloro-aniline

bromochlorobenzene

ortho-tolylmagnesium bromide

1,6-bis-(4-chlorophenyl)-3,4-diacetyl-1,5-hexazadiene

Refernces

• 1、 Ahmed, Jasimuddin,Chakraborty, Soumi,Jose, Anex,Sreejyothi,Mandal, Swadhin K.. "Integrating Organic Lewis Acid and Redox Catalysis: The Phenalenyl Cation in Dual Role". supporting information. p. 8330 - 8339. Retrieved 2018/06/19.
• 2、 Ikoma,Ando,Naoi,Akiyama,Sugimori. "Halogen selectivity in nickel salt-catalyzed cross-coupling of aryl Grignard reagents with bromochlorobenzenes - A novel synthetic method of unsymmetrical terphenyl". . p. 481 - 487. Retrieved 2007/10/02.