25570-02-9

Basic information

• Product Name: 3,3',5,5'-TETRAMETHYLBIPHENYL
• Synonyms: 1,1'-Biphenyl, 3,3',5,5'-tetramethyl-;3,3',5,5'-Tetramethyl-1,1'-biphenyl;Biphenyl, 3,3',5,5'-tetramethyl-;3,3',5,5'-TETRAMETHYLBIPHENYL;3,3'',5,5''-TETRAMETHYLBIPHENYL, 97+%
• CAS NO: 25570-02-9
• Molecular Formula: C₁₆H₁₈
• Molecular Weight: 210.31
• Mol File: 25570-02-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 47-49°C
• Boiling Point: 300.9°Cat760mmHg
• Flash Point: 138.7°C
• Appearance: /
• Density: 0.956g/cm³
• BRN: 1935931
• CAS DataBase Reference: 3,3',5,5'-TETRAMETHYLBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3',5,5'-TETRAMETHYLBIPHENYL(25570-02-9)
• EPA Substance Registry System: 3,3',5,5'-TETRAMETHYLBIPHENYL(25570-02-9)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 22-24/25-61-60
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 2
• Hazardous Substances Data: 25570-02-9(Hazardous Substances Data)

Usage

Description

3,3',5,5'-Tetramethylbiphenyl is an organic compound with a biphenyl core structure, featuring two phenyl rings connected by a carbon-carbon bond. Each phenyl ring has two methyl groups attached, specifically at the 3' and 5' positions, resulting in a symmetrical and stable molecular structure. 3,3',5,5'-TETRAMETHYLBIPHENYL is known for its chemical properties and potential applications in various industries.

Uses

Used in Chemical Synthesis:
3,3',5,5'-Tetramethylbiphenyl is used as a precursor for the preparation of 3,3',5,5'-tetramethylenebiphenyl tetraanion, which is an important intermediate in the synthesis of various organic compounds and materials. Its symmetrical structure and stability make it a suitable candidate for further chemical modifications and reactions.
Used in Material Science:
In the field of material science, 3,3',5,5'-Tetramethylbiphenyl is used to prepare biphenyl-3,3',5,5'-tetracarboxylic acid by the oxidation with potassium permanganate. This acid derivative has potential applications in the development of advanced polymers and materials with specific properties, such as enhanced thermal stability, mechanical strength, or electrical conductivity.

Upstream product

• 105-36-2 ethyl bromoacetate 
• 172975-69-8 3,5-dimethylphenyl boronic acid 
• 556-96-7 5-bromo-1,3-xylene 
• 73020-77-6 <18O>-1-phenyl-1-ethanol 
• 78-92-2 iso-butanol 
• 623-03-0 4-Cyanochlorobenzene 
• 325142-93-6 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 623-00-7 4-bromobenzenecarbonitrile 
• 132921-00-7 Chloro-bis-(3,5-dimethyl-phenyl)-silane 
• 95-48-7 ortho-cresol 
• 1137088-28-8 (3,5-dimethylphenyl)(triphenyl-λ5-phosphanyl)gold 
• 373623-34-8 C₈H₉BrZn 
• 19798-58-4 N-chloro-n-butylamine 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 4371-28-2 biphenyl-3,3',5,5'-tetracarboxylic acid 
• 359685-05-5 (η(6)-3,5,3',5'-tetramethylbiphenyl)titanium(II)-bis(tetrachloroaluminate) 
• 56667-01-7 3,3',4,4',5,5'-hexamethylbiphenyl 

Relevant articles and documents

Discovery and mechanistic investigation of Pt-catalyzed oxidative homocoupling of benzene with PhI(OAc)2

We present a Pt-catalyzed direct coupling of benzene to biphenyl. This catalytic reaction employs a cyclometalated platinum(ii) complex [PtMe(bhq)(SMe2)] (bhq = benzo[h]quinolate) with PhI(OAc)2 as an oxidant and does not require an acid, a co-catalyst or a solvent. The reaction kinetics and characterization of potential catalytic species are reported. The reaction is first-order in Pt and second-order in benzene, which implicates the second C-H activation step as rate-determining. A Pt(ii)/Pt(iv) catalytic cycle is suggested. The reaction commences by oxidation of the Pt(ii) complex to give the platinum(iv) species [Pt(bhq)(SMe2)(OAc)2](OAc) followed by C-H activation of benzene to afford the intermediate [PtPh(bhq)(SMe2)(OAc)](OAc) concurrently with the release of HOAc. A second benzene molecule reacts similarly to give the diphenyl intermediate [PtPh2(bhq)(SMe2)](OAc). C-C bond forming reductive elimination ensues to regenerate Pt(ii) and complete the catalytic cycle. The proposed mechanism has been examined by DFT computations, which provide support to experimental findings.

Cobalt-catalyzed electrophilic amination of arylzincs with N-chloroamines

Roles reversed: An efficient cobalt-catalyzed electrophilic amination of arylzinc reagents has been achieved. A variety of functionalized arylzincs and N-chloroamines were coupled under mild conditions (see scheme). Both secondary and tertiary arylamines were obtained in moderate to excellent yields. Copyright

Combining Homogeneous Catalysis with Heterogeneous Separation using Tunable Solvent Systems

Tunable solvent systems couple homogeneous catalytic reactions to heterogeneous separations, thereby combining multiple unit operations into a single step and subsequently reducing waste generation and improving process economics. In addition, tunable solvents can require less energy than traditional separations, such as distillation. We extend the impact of such solvents by reporting on the application of two previously described carbon dioxide tunable solvent systems: polyethylene glycol (PEG)/organic tunable solvents (POTS) and organic/aqueous tunable solvents (OATS). In particular, we studied: (1) the palladium catalyzed carbon-oxygen coupling of 1-bromo-3,5-dimethylbenzene and o-cresol to potassium hydroxide to produce o-tolyl-3,5-xylyl ether and 1-bromo-3,5-di-tert-butylbenzene to potassium hydroxide to produce 3,5-di-tert-butylphenol in PEG400/1,4-dioxane/water and (2) the rhodium-catalyzed hydroformylation of p-methylstyrene in water/ acetonitrile to form 2-(p-tolyl) propanal. In addition, we introduce a novel tunable solvent system based on a modified OATS where propane replaces carbon dioxide. This represents the first use of propane in a tunable solvent system.