15519-73-0

Basic information

• Product Name: 4,4'-Dimethyl-2,2'-bi(phenol)
• Synonyms: 2,2'-Bi[4-methylphenol];4,4'-Dimethyl-2,2'-bi(phenol);5,5'-Dimethyl-1,1'-biphenyl-2,2'-diol
• CAS NO: 15519-73-0
• Molecular Formula: C₁₄H₁₄O₂
• Molecular Weight: 214.26
• Mol File: 15519-73-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 153.5°C
• Boiling Point: 314.4°C (rough estimate)
• Appearance: /
• Density: 1.0781 (rough estimate)
• Refractive Index: 1.5570 (estimate)
• CAS DataBase Reference: 4,4'-Dimethyl-2,2'-bi(phenol)(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Dimethyl-2,2'-bi(phenol)(15519-73-0)
• EPA Substance Registry System: 4,4'-Dimethyl-2,2'-bi(phenol)(15519-73-0)

Safety Data

• Hazardous Substances Data: 15519-73-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 3248, 1994 DOI: 10.1021/jo00091a003Tetrahedron Letters, 33, p. 2207, 1992 DOI: 10.1016/0040-4039(92)88178-8

Upstream product

• 106-44-5 p-cresol 
• 94-36-0 dibenzoyl peroxide 
• 6933-26-2 (5-ethyl-2-thienyl)phenylmethanone 
• 65109-76-4 N-p-toluenesulfonyl-O-(4-tolyl)-hydroxylamine 
• 2589-57-3 2-(1-methoxycarbonyl-1-methylethylazo)-2-methylpropionic acid methyl ester 
• 129194-36-1 bis(3,5-dimethoxybenzoyl) peroxide 
• 129194-37-2 bis(3,4-dimethoxybenzoyl) peroxide 
• 1712-86-3 bis-(3-methoxy-benzoyl)-peroxide 
• 849-83-2 bis(4-methoxybenzoyl) peroxide 
• 1712-84-1 p-nitrobenzoyl peroxide 
• 129194-38-3 C₂₀H₂₂O₁₀ 
• 119-61-9 benzophenone 
• 72001-37-7 7-methoxy-4-(1-methyl-4-oxo-2,5-cyclohexadien-1-yl)-2H-1,4-benzoxazin-3(4H)-one 
• 67-56-1 methanol 

Downstream Products

• 92806-40-1 2,2',2,2'''-Tetrahydroxy-5,5',5,5'''-tetramethyl-1,1':3',1:3,1'''-quaterphenyl 
• 71128-94-4 2,2'''-Dimethoxy-5,5',5'',5'''-tetramethyl-[1,3';1',1'';3'',1''']quaterphenyl-2',2''-diol 
• 155351-62-5 2,9-Bis-(3'-bromo-2,2'-diethoxy-5,5'-dimethyl-biphenyl-3-yl)-[1,10]phenanthroline 
• 155351-59-0 2,9-Bis-(2,2'-diethoxy-5,5'-dimethyl-biphenyl-3-yl)-[1,10]phenanthroline 
• 155351-61-4 C₄₀H₃₀Br₂N₂O₄ 
• 155351-60-3 C₄₀H₃₂N₂O₄ 
• 24046-10-4 6-Oxy-6'-methoxy-3.3'-dimethyl-diphenyl 
• 3402-82-2 5,5'-Dimethyl-2,2'-bis-(2-nitro-phenoxy)-biphenyl 

Relevant articles and documents

Development of the radical C–O coupling reaction of phenols toward the synthesis of natural products comprising a diaryl ether skeleton

Compounds comprising a diaryl ether skeleton exist among natural phenols. The diaryl ether skeleton is thought to be biosynthesized through the coupling of two or more phenols. It is an important structural feature in medicines and agrochemicals, and it is imperative to develop methods for constructing such skeletons in organic synthesis. However, by the synthesis method through the coupling of phenols, coupling occurs preferentially at the ortho-substituted carbon atom of phenols. In this study, various radical-generating reagents and conditions were investigated with the aim of developing a short-step construction method of the diaryl ether skeleton by the radical homo-coupling of two phenol molecules. In addition, cross-coupling reactions between radicals of 2,4,6-tri-tert-butylphenol and p-substituted phenol were conducted to synthesize eight C (ortho)–O coupling products. Based on the results, a computational chemical approach was employed to verify the cause of C (ortho)–O bond formation.

Cu(OAc)2-catalyzed remote benzylic C(sp3)-H oxyfunctionalization for C=O formation directed by the hindered para-hydroxyl group with ambient air as the terminal oxidant under ligand- and additive-free conditions

A hindered para-hydroxyl group-directed remote benzylic C(sp3)-H oxyfunctionalization has been developed for the straightforward transformation of 2,6-disubstituted 4-cresols, 4-alkylphenols, 4-hydroxybenzyl alcohols and 4-hydroxybenzyl alkyl ethers into various aromatic carbonyl compounds. The ligand- and additive-free Cu(OAc)2-catalyzed atmospheric oxidation mediated by ethylene glycol unlocks a facile, atom-economical, and environmentally benign C=O formation for the functionalization of primary and secondary benzyl groups. Due to the pharmaceutical importance of 4-hydroxybenzaldehydes and 4-hydroxyphenones, the methodology is expected to be of significant value for both fundamental research and practical applications.

Isolation of cross-coupling products in model studies on the photochemical modification of proteins by tiaprofenic acid

To gain insight into the chemical nature of drug-induced photoallergy, model studies have been carried out on the photochemical modification of proteins by tiaprofenic acid. Irradiation of decarboxylated tiaprofenic acid (DTPA) in the presence of p-cresol leads to C-C- and C-O-connected p-cresol 'dimers', together with DTPA hydrodimers. The p-cresol-DTPA cross-coupling product was not detected in this reaction. However, a product of this type is formed using a more hindered phenol, such as 2,6-di-tert-butylphenol. Similar results are obtained when tiaprofenic acid (TPA) or its methyl ester are used as photosensitizers. The observed formation of 'dimers' can be related to protein photo-crosslinking, through the coupling of two tyrosine units. On the other hand, phenol-(D)TPA cross-coupling may be relevant to the understanding of drug-protein photobinding.