141989-18-6

Basic information

• Product Name: 5,5′-bis(4-hydroxyphenyl)-2,2′-dihydroxy-1,1′-biphenyl
• Synonyms: 5,5′-bis(4-hydroxyphenyl)-2,2′-dihydroxy-1,1′-biphenyl
• CAS NO: 141989-18-6
• Molecular Weight: 370.405
• Mol File: 141989-18-6.mol

Chemical Properties

• CAS DataBase Reference: 5,5′-bis(4-hydroxyphenyl)-2,2′-dihydroxy-1,1′-biphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5′-bis(4-hydroxyphenyl)-2,2′-dihydroxy-1,1′-biphenyl(141989-18-6)
• EPA Substance Registry System: 5,5′-bis(4-hydroxyphenyl)-2,2′-dihydroxy-1,1′-biphenyl(141989-18-6)

Safety Data

• Hazardous Substances Data: 141989-18-6(Hazardous Substances Data)

Upstream product

• 528853-19-2 5,5'-dibromo-2,2'-bis(methoxymethyloxy)biphenyl 
• 34261-55-7 5,5'-dibromo-2,2'-dihydroxybiphenyl 
• 1806-29-7 2,2'-dihydroxybiphenyl 
• 6793-92-6 p-benzyloxyphenylbromide 
• 106-41-2 4-bromo-phenol 
• 92-88-6 4,4'-Dihydroxybiphenyl 

Relevant articles and documents

Solvent-controlled selective synthesis of biphenols and quinones: Via oxidative coupling of phenols

A regioselective synthesis of unsymmetrical and symmetrical biphenols and binaphthols via oxidative coupling of phenols or naphthols in the presence of K2S2O8 in CF3COOH under ambient conditions is described. Interestingly, the 1:1 ratio of H2O and CH3CN solvent mixtures at 80 °C instead of CF3COOH provided substituted unsymmetrical quinones. A gram-scale synthesis of biphenols and binaphthols was demonstrated.

Interplay between the crystal stability and the energy of the molecular conformation

A specially designed new compound, 5,5′-bis(4-hydroxyphenyl)-2,2′-dihydroxy-1,1′-biphenyl, can crystallize in different crystallographic systems. The molecule adopts theC-conformation for the torsion angle of around 60° and theT-conformation for the angle of around 130°, which differ in energy by ～0.8 kJ mol?1. Theoretical studies for the gaseous phase show that theC-conformer has a lower energy. However, crystallization experiments show that the most stable crystal structure consists of only the energetically less stableT-conformer. On the other hand, fast crystal growth at low temperature and crystal growth after milling both lead to the formation of metastable crystals in which the studied molecule adopts theC-conformation. Our study shows that the total crystal net energy is the main factor in determining the molecular conformations even if the molecular conformation has a higher energy in the gaseous phase.

Regiochemical Control in the Oxidative Coupling of Metal Phenolates: Highly Selective Synthesis of Symmetric, Hydroxylated Biaryls

Oxidative coupling of highly coordinating metal phenolates promoted by FeCl3 afforded variously substituted symmetric 2,2'-dihydroxy biaryls in good yield and high regiochemical control. Key words: Oxidative coupling; metal phenolates; 2,2'-dihydroxy biar

Oxidative coupling of dichloroaluminium phenolates: Highly selective synthesis of hydroxylated Bi- and tetraaryls

Dichloroaluminium phenolates 4 undergo highly selective FeCl3-promoted oxidative coupling. Variously substituted symmetric 2,2′-dihydroxy biaryls 2 are obtained in good yields and excellent selectivities. The chelation control in the final reaction products 7 promotes the chemoselectivity of the process.