2,2'-DIMETHYLBIPHENYL

Base Information

• Chemical Name: 2,2'-DIMETHYLBIPHENYL
• CAS No.: 32587-64-7
• Molecular Formula: C22H18
• Molecular Weight: 282.385
• Hs Code.: 2902909090
• Mol file: 32587-64-7.mol

Synonyms:1,1'-Binaphthalene,2,2'-dimethyl-, (S)-;1,1'-Binaphthyl, 2,2'-dimethyl-, (+)- (8CI);(+)-2,2'-Dimethylbinaphthyl;(S)-(+)-2,2'-Dimethyl-1,1'-binaphthalene;(S)-2,2'-Dimethyl-1,1'-binaphthalene;(S)-2,2'-Dimethyl-1,1'-binaphthyl;

Chemical Property of 2,2'-DIMETHYLBIPHENYL

Chemical Property:

• Melting Point: 18 °C
• Refractive Index: n20/D 1.5745(lit.)
• Boiling Point: 401.8 °C at 760 mmHg
• Flash Point: 192.3 °C
• PSA: 0.00000
• Density: 1.105 g/cm³
• LogP: 3.97040

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-2,2''-Dimethyl-1,1''-binaphthyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,2'-DIMETHYLBIPHENYL

There total 62 articles about 2,2'-DIMETHYLBIPHENYL 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: 100.0%

1-bromo-2-methylnaphtalene (2586-62-1) + 2-methyl-1-naphthylboronic acid (103989-84-0) → 2,2'-dimethyl-1,1'-binaphthyl (60536-98-3,19634-89-0,32587-64-7,32834-84-7)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; In tetrahydrofuran; for 30h; Inert atmosphere; Reflux;

DOI:10.1016/j.jorganchem.2011.04.031

Reference yield: 100.0%

methylmagnesium bromide (75-16-1) + (+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl (141807-44-5,126613-06-7,128544-05-8,128575-34-8) → 2,2'-dimethyl-1,1'-binaphthyl (60536-98-3,19634-89-0,32587-64-7,32834-84-7)

Guidance literature:

With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In diethyl ether; at 0 ℃; for 24h; Reflux;

DOI:10.1002/anie.201201374

Reference yield: 98.0%

1-bromo-2-methylnaphtalene (2586-62-1) + (2-methyl-1-naphthyl)magnesium bromide (21450-90-8) → 2,2'-dimethyl-1,1'-binaphthyl (60536-98-3,19634-89-0,32587-64-7,32834-84-7)

Guidance literature:

With [Pd(μ-Cl)Cl(N,N′-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)imidazol-2-ylidene)]₂; In 1,4-dioxane; at 60 ℃; for 16h; Inert atmosphere; Glovebox;

DOI:10.1039/c4ob01269k

upstream raw materials:

1-bromo-2-methylnaphtalene

methylmagnesium bromide

(+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl

4,5-dihydro-4,4-dimethyl-3H-dinaphtho<2,1-a:1',2'-e>stannepin

Refernces

• 1、 Yang, He,Sun, Jiawei,Gu, Wei,Tang, Wenjun. "Enantioselective cross-coupling for axially chiral tetra-ortho-substituted biaryls and asymmetric synthesis of gossypol". supporting information. p. 8036 - 8043. Retrieved 2020/05/27.
• 2、 Patel, Nitinchandra D.,Sieber, Joshua D.,Tcyrulnikov, Sergei,Simmons, Bryan J.,Rivalti, Daniel,Duvvuri, Krishnaja,Zhang, Yongda,Gao, Donghong A.,Fandrick, Keith R.,Haddad, Nizar,Lao, Kendricks So,Mangunuru, Hari P. R.,Biswas, Soumik,Qu, Bo,Grinberg, Nelu,Pennino, Scott,Lee, Heewon,Song, Jinhua J.,Gupton, B. Frank,Garg, Neil K.,Kozlowski, Marisa C.,Senanayake, Chris H.. "Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra- ortho-Substituted Biaryl Synthesis". . p. 10190 - 10209. Retrieved 2018/10/20.