3976-35-0

Basic information

• Product Name: 2,4,6-Trimethyl-1,1'-biphenyl
• Synonyms: 2,4,6-Trimethyl-1,1'-biphenyl;1,3,5-Trimethyl-2-phenylbenzene;2,4,6-Trimethylbiphenyl
• CAS NO: 3976-35-0
• Molecular Formula: C₁₅H₁₆
• Molecular Weight: 196.28754
• Mol File: 3976-35-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 275 °C at 760 mmHg
• Flash Point: 118.7 °C
• Appearance: /
• Density: 0.964g/cm³
• Vapor Pressure: 0.00878mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: 2,4,6-Trimethyl-1,1'-biphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Trimethyl-1,1'-biphenyl(3976-35-0)
• EPA Substance Registry System: 2,4,6-Trimethyl-1,1'-biphenyl(3976-35-0)

Safety Data

• Hazardous Substances Data: 3976-35-0(Hazardous Substances Data)

Usage

General Description

2,4,6-Trimethyl-1,1'-biphenyl, also known as tri-p-tolyl benzene, is a chemical compound that consists of a central biphenyl core with three methyl groups attached to different positions on the aromatic rings. It is a colorless solid with a faint aromatic odor and is insoluble in water. 2,4,6-Trimethyl-1,1'-biphenyl is used as a raw material in the production of various chemicals and is also employed as a stabilizer for organic and peroxide-based compounds. Additionally, it is utilized in the manufacturing of liquid crystal displays and as a heat transfer fluid in high-temperature applications. While it is relatively stable and has low acute toxicity, prolonged exposure to high concentrations of 2,4,6-trimethyl-1,1'-biphenyl may cause irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C15H16/c1-11-9-12(2)15(13(3)10-11)14-7-5-4-6-8-14/h4-10H,1-3H3

Upstream product

• 65881-97-2 dimesityl(phenyl)borane 
• 108-86-1 bromobenzene 
• 98-80-6 phenylboronic acid 
• 71-43-2 benzene 
• 703-18-4 phenyl trifluoromethyl sulfoxide 
• 4028-63-1 iodomesitylene 
• 5980-97-2 mesitylboronic acid 
• 20623-88-5 potassium diphenyldimesitylborate 
• 356031-47-5 2,4,6-trimethylphenyl p-toluenesulfonate 

Downstream Products

• 1260405-05-7 4,4″-bis(2,4,6-trimethyl-[1,1′-biphenyl]-3-yl)-1,1′:4′,1″-ternaphthalene 
• 1448855-14-8 4,4′′′′′-bis(2,4,6-trimethylbiphenyl-3-yl)-1,1′:4′,1″:4″,1?:4?,1′′′′:4′′′′,1′′′′′-sexinaphthalene 
• 1260405-00-2 4,4?-bis(2,4,6-trimethylbiphenyl-3-yl)-1,1′:4′,1″:4″,1?-quaternaphthalene 
• 65-85-0 benzoic acid 
• 1364188-40-8 N-(3'-phenyl-2',4',6'-trimethylbiphenyl-4-yl)-N-(3-phenyl-2,4,6-trimethylphenyl)acetamide 
• 1260404-96-3 4,4'-bis(2,4,6-trimethylbiphenyl-3-yl)-1,1'-binaphthyl 
• 1015256-04-8 7-bromo-1-[2,4,6-trimethyl(biphenyl)-3-yl]naphthalene 
• 131563-99-0 rac-3,3'-diphenylbimesityl 
• 131456-79-6 2,2'',4,4'',6,6''-hexamethyl-1,1':3',1'':3'',1'''-quaterphenyl 

Relevant articles and documents

Palladium-Catalyzed Arylation of Arylboronic Acids with Yagupolskii-Umemoto Reagents

A Pd-catalyzed Suzuki cross-coupling of arylboronic acids with Yagupolskii-Umemoto reagents was explored. In contrary to trifluoromethylations, the Pd-catalyzed reaction of R-B(OH)2 and [Ar2SCF3]+[OTf]- provided the arylation products (R-Ar) in good to high yields. The reaction confirms that the S-Ar bonds of [Ar2SCF3]+[OTf]- can be readily cleaved in the presence of Pd complexes. The relatively electron-poor aryl groups of asymmetric [Ar1Ar2SCF3]+[OTf]- salts are more favorably transferred compared to the electron-rich ones. This reaction represents the first report of utilization of [Ar2SCF3]+[OTf]- as arylation reagents in organic synthesis.

Revealing a second transmetalation step in the Negishi coupling and its competition with reductive elimination: Improvement in the interpretation of the mechanism of biaryl syntheses

This paper presents an experimental and theoretical investigation of the Pd-catalyzed Negishi coupling reaction and reveals a novel second transmetalation reaction between an Ar1-Pd-Ar2 species and the organozinc reagent Ar2-ZnX. Understanding of this second step reveals how homocoupling and dehalogenation products are formed. Thus, the second transmetalation generates Ar2PdAr2 and Ar 1ZnCl, which upon reductive elimination and hydrolysis, respectively, give the homocoupling product Ar2-Ar2 and the dehalogenation product Ar1H. The ratio of the cross-coupling product Ar1-Ar2 and the homocoupling product Ar 2-Ar2 is determined by competition between the second transmetalation and reductive elimination steps. This mechanism is further supported by density functional theoretical calculations. Calculations on a series of reactions suggest a strategy in controlling the selectivity of cross-coupling and homocoupling pathways, which we have experimentally verified.

Kumada coupling of aryl and vinyl tosylates under mild conditions

Aryl and alkenyl tosylates are easily prepared, inexpensive and, thus, attractive for transition-metal-catalyzed couplings, but their reactivity is low. We report examples of mild, palladium-catalyzed coupling of aryl, alkenyl, and alkyl Grignard reagents with aryl and alkenyl tosylates. The resulting biaryls, vinylarenes, and alkylarenes were isolated in good to excellent yield. These couplings were conducted with a nearly equimolar ratio of the two reactants, and many examples were conducted at room temperature.