2,6-Dimethylbiphenyl

Base Information

• Chemical Name: 2,6-Dimethylbiphenyl
• CAS No.: 3976-34-9
• Molecular Formula: C14H14
• Molecular Weight: 182.265
• UNII: 7H1B8IXB53
• DSSTox Substance ID: DTXSID70192840
• Nikkaji Number: J402.961E
• Wikidata: Q83065506
• Mol file: 3976-34-9.mol

Synonyms:2,6-DIMETHYLBIPHENYL;3976-34-9;1,1'-Biphenyl, 2,6-dimethyl-;1,3-dimethyl-2-phenylbenzene;2,6-DIMETHYL-1,1'-BIPHENYL;Biphenyl, 2,6-dimethyl-;7H1B8IXB53;2.6-dimethylbiphenyl;UNII-7H1B8IXB53;2,6-Dimethyl-1,1-biphenyl;DTXSID70192840;MFCD14701794

Chemical Property of 2,6-Dimethylbiphenyl

Chemical Property:

• Vapor Pressure: 0.0212mmHg at 25°C
• Melting Point: -2.5°C
• Refractive Index: 1.5745
• Boiling Point: 259.3°Cat760mmHg
• Flash Point: 106.5°C
• PSA: 0.00000
• Density: 0.973g/cm³
• LogP: 3.97040
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 182.109550447
• Heavy Atom Count: 14
• Complexity: 157

Purity/Quality:

99%min ^*data from raw suppliers

2,6-Dimethylbiphenyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)C)C2=CC=CC=C2
• Uses: 2,6-Dimethylbiphenyl acts as a reagent in the preparation of palladium catalyst for Suzuki-Miyaura cross-coupling reactions.

Technology Process of 2,6-Dimethylbiphenyl

There total 11 articles about 2,6-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: 65.0%

2-Bromo-m-xylene (576-22-7) + 1-phenyl-2,8,9-trioxa-5-aza-1-silabicyclo{3.3.3}undecane (2097-19-0) → biphenyl (92-52-4,1594-86-1) + 2,6-dimethyl-1,1′-biphenyl (3976-34-9)

Guidance literature:

With tetrabutyl ammonium fluoride; triphenylphosphine; palladium diacetate; In tetrahydrofuran; N,N-dimethyl-formamide; Heating;

DOI:10.1021/jo034809g

Reference yield:

2-Bromo-m-xylene (576-22-7) + phenyl trimethylsiloxane (2996-92-1,46143-12-8) → biphenyl (92-52-4,1594-86-1) + 2,6-dimethyl-1,1′-biphenyl (3976-34-9)

Guidance literature:

With tetrabutyl ammonium fluoride; triphenylphosphine; palladium diacetate; In tetrahydrofuran; N,N-dimethyl-formamide; at 83 ℃; for 23.5h;

DOI:10.1021/ol991186d

Reference yield:

2,6-dimethyliodobenzene (608-28-6) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → biphenyl (92-52-4,1594-86-1) + 2,6-dimethyl-1,1′-biphenyl (3976-34-9) + m-xylene (108-38-3,104809-90-7)

Guidance literature:

With N,N’-[(±)-trans-cyclohexane-1,2-diyl]bis(N-methylformamide); potassium tert-butylate; at 110 ℃; for 4h; Reagent/catalyst; Mechanism; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.6b03282

upstream raw materials:

para-xylene

benzene

m-xylene

cyclohexanol

Downstream raw materials:

9-Brom-18-phenyl-2,11-dithia<3.3>metacyclophan

9,18,27,36-Tetraphenyl-2,11,20,29-tetrathia<3.3.3.3>metacyclophan-2,2,11,11,20,20,29,29-octaoxid

9,18,27,36-Tetraphenyl-2,11,20,29-tetrathia<3.3.3.3>metacyclophan

12,24-Diphenyl-2,5,14,17-tetrathia<6.6>metacyclophan-2,2,5,5,14,14,17,17-octaoxid

Refernces

• 1、 Emery, Katie J.,Tuttle, Tell,Murphy, John A.. "Evidence of single electron transfer from the enolate anion of an: N, N ′-dialkyldiketopiperazine additive in BHAS coupling reactions". . p. 8810 - 8819. Retrieved 2017/11/03.
• 2、 Monnereau, Laure,El Moll, Hani,Sémeril, David,Matt, Dominique,Toupet, Lo?c. "Resorcinarenyl-phosphines in suzuki-miyaura cross-coupling reactions of aryl chlorides". supporting information. p. 1364 - 1372. Retrieved 2015/04/27.