26567-10-2

Basic information

• Product Name: 3,3',5,5'-TETRAMETHYL-2,2'-BIPHENOL
• Synonyms: 3,3',5,5'-TETRAMETHYL-2,2'-BIPHENOL;2-(2-hydroxy-3,5-dimethylphenyl)-4,6-dimethylphenol;3,3,5,5-TETRAMETHYL-[1,1-BIPHENYL]-2,2-DIOL
• CAS NO: 26567-10-2
• Molecular Formula: C₁₆H₁₈O₂
• Molecular Weight: 242.31
• Mol File: 26567-10-2.mol
• Article Data: 37

Chemical Properties

• Melting Point: 134-136°C
• Boiling Point: 341℃ at 101.3kPa
• Appearance: white/Powder
• CAS DataBase Reference: 3,3',5,5'-TETRAMETHYL-2,2'-BIPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3',5,5'-TETRAMETHYL-2,2'-BIPHENOL(26567-10-2)
• EPA Substance Registry System: 3,3',5,5'-TETRAMETHYL-2,2'-BIPHENOL(26567-10-2)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 26567-10-2(Hazardous Substances Data)

Usage

Description

3,3',5,5'-Tetramethyl-2,2'-biphenol, commonly known as Durene, is a white crystalline solid with the molecular formula C16H18O. It is insoluble in water but soluble in organic solvents. This chemical compound serves various functions in different industries, including as a stabilizer, antioxidant, polymerization inhibitor, crosslinking agent, and raw material for specialty chemicals and pharmaceuticals.

Uses

Used in Plastics and Rubber Industry:
3,3',5,5'-Tetramethyl-2,2'-biphenol is used as a stabilizer and antioxidant in the manufacturing of plastics and rubber. It helps prevent the degradation of these materials, thereby extending their lifespan and maintaining their properties.
Used in Acrylic and Methacrylic Monomers Production:
In the production of acrylic and methacrylic monomers, 3,3',5,5'-Tetramethyl-2,2'-biphenol is used as a polymerization inhibitor. It prevents unwanted polymerization reactions, ensuring the quality and purity of the final product.
Used in Epoxy Resin Production:
3,3',5,5'-Tetramethyl-2,2'-biphenol is utilized as a crosslinking agent in the production of epoxy resins. It enhances the mechanical and thermal properties of the resins, making them suitable for various applications, such as coatings, adhesives, and composite materials.
Used in Specialty Chemicals and Pharmaceuticals:
3,3',5,5'-Tetramethyl-2,2'-biphenol serves as a raw material in the production of specialty chemicals and pharmaceuticals. Its unique chemical structure allows for the synthesis of various compounds with specific properties and applications.
Used in Cosmetics and Personal Care Products:
Due to its antimicrobial and antifungal properties, 3,3',5,5'-Tetramethyl-2,2'-biphenol is used in the preservation of cosmetics and personal care products. It helps maintain the quality and safety of these products by preventing the growth of harmful microorganisms.
However, it is crucial to handle 3,3',5,5'-Tetramethyl-2,2'-biphenol with care, as it may cause skin and eye irritation and is harmful if swallowed or inhaled. Proper safety measures should be taken during its use and handling to minimize potential risks.

Upstream product

• 70853-94-0 N-(2,4-dimethylphenyl)hydroxylamine 
• 110-22-5 diacetyl peroxide 
• 64-19-7 acetic acid 
• 105-67-9 2,4-Xylenol 
• 64-17-5 ethanol 
• 7705-08-0 iron(III) chloride 
• 7791-25-5 sulfuryl dichloride 
• 7664-93-9 sulfuric acid 
• 35523-91-2 2,4-dimethylphenyl azide 
• 51770-93-5 4-hydroxy-2,4-dimethyl-2,5-cyclohexadienone 
• 10035-10-6 hydrogen bromide 
• 20340-62-9 tris(2,4-dimethylphenoxy)borone 
• 93-51-6 2-Methoxy-4-methylphenol 
• 90003-93-3 1-iodo-3,5-dimethyl-4-hydroxybenzene 

Downstream Products

• 1032106-33-4 ethyl (2'-ethoxycarbonylmethoxy-3,5,3',5'-tetramethylbiphenyl-2-yloxy)acetate 
• 938058-85-6 2-hydroxy-3,3',5,5'-tetramethyl-2'-tosyloxy-1,1'-biphenyl 

Relevant articles and documents

Selective and Scalable Dehydrogenative Electrochemical Synthesis of 3,3,5,5-Tetramethyl-2,2-biphenol

3,3,5,5-Tetramethyl-2,2-biphenol is a compound of high technical significance, as it exhibits superior properties as building block for ligands in the transition-metal catalysis. However, side reactions and overoxidation are challenging issues in the conventional synthesis of this particular biphenol. Here, an electrochemical method is presented as powerful and sustainable alternative to conventional chemical strategies, which gives good yields up to 51percent. Despite using inexpensive and well-available bromide-containing supporting electrolytes, the issue of bromination and general byproduct formation is effectively suppressed by adding water to the electrolyte. Additionally, the scalability of this method was demonstrated by conducting the electrolysis on a 122 g scale.

Unexpected highly chemoselective anodic ortho-coupling reaction of 2,4-dimethylphenol on boron-doped diamond electrodes

Anodic conversion of 2,4-dimethylphenol on boron-doped diamond (BDD) electrodes under solvent-free conditions results in an unusual highly selective formation of the desired 2,2′-biphenol, representing the best electrochemical synthesis for this particular compound. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Supporting-Electrolyte-Free and Scalable Flow Process for the Electrochemical Synthesis of 3,3′,5,5′-Tetramethyl-2,2′-biphenol

The most efficient electrochemical synthesis of 3,3′,5,5′-tetramethyl-2,2′-biphenol by dehydrogenative coupling is reported. The electrolysis is performed supporting-electrolyte-free in 1,1,1,3,3,3-hexafluoroisopropanol and at carbon electrodes, whereby glassy carbon electrodes turned out to be superior. To provide sufficient conductivity, pyridine is added, and it can easily be recovered by evaporation and reused. This facilitates the downstream process tremendously, making it simple, economical, and technically viable. The scalability was proven by establishing a flow electrolysis in differently sized narrow-gap flow electrolyzers. Carrying out a multistep cascade electrolysis enabled the challenging hydrogen evolution to be successfully addressed. The scaled-up electrolysis provided an isolated yield of 59% biphenol.

Oxidative photocatalytic homo- And cross-coupling of phenols: Nonenzymatic, catalytic method for coupling tyrosine

An oxidative photocatalytic method for phenol? phenol homo- and cross-coupling is described, and isolated yields of 16?97% are obtained. Measured oxidation potentials and computed nucleophilicity parameters support a mechanism of nucleophilic attack of one partner onto the oxidized neutral radical form of the other partner. Our understanding of this model permitted the development of cross-coupling reactions between nucleophilic phenols/arenes and easily oxidized phenols with high selectivity and efficiency. A highlight of this method is that one equivalent of each coupling partner is utilized. Building on these findings, a nonenzymatic, catalytic method for coupling tyrosine was also developed.

Selective, Catalytic, and Metal-Free Coupling of Electron-Rich Phenols and Anilides Using Molecular Oxygen as Terminal Oxidant

Selective oxidative homo- and cross-coupling of electron-rich phenols and anilides was developed using nitrosonium tetrafluoroborate as a catalyst. Oxidative coupling of phenols revealed unusual selectivities, which translated into the unprecedented synthesis of inverse Pummerer-type ketones. Mechanistic studies suggest that oxidative coupling of phenols and anilides shares a common pathway via homolytical heteroatom-hydrogen bond cleavage. Nitrosonium salt catalysis was applied for cross-dehydrogenative coupling initiated by generation of heteroatom-centered radicals.