92-05-7

Basic information

• Product Name: 3.4-BIPHENYLDIOL
• Synonyms: [1,1’-biphenyl]-3,4-diol;[1,1'-Biphenyl]-3,4-diol;1,2-Benzenediol, 4-phenyl-;3,4-Dihydroxybiphenyl;4-Phenyl-1,2-benzenediol;4-Phenylcatechol;Biphenyl, 3,4-dihydroxy;biphenyl-3,4-diol
• CAS NO: 92-05-7
• Molecular Formula: C12H10O2
• Molecular Weight: 186.2066
• EINECS: 202-121-6
• Mol File: 92-05-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 139.35°C
• Boiling Point: 280.69°C (rough estimate)
• Flash Point: 182.6°C
• Appearance: /
• Density: 1.1032 (rough estimate)
• Vapor Pressure: 7.02E-06mmHg at 25°C
• Refractive Index: 1.6010 (estimate)
• CAS DataBase Reference: 3.4-BIPHENYLDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3.4-BIPHENYLDIOL(92-05-7)
• EPA Substance Registry System: 3.4-BIPHENYLDIOL(92-05-7)

Safety Data

• Hazardous Substances Data: 92-05-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 2915, 1996 DOI: 10.1016/0040-4039(96)00446-7

InChI:InChI=1/C12H10O2/c13-11-7-6-10(8-12(11)14)9-4-2-1-3-5-9/h1-8,13-14H

Upstream product

• 35489-86-2 4-phenylcyclohexane-1,2-dione 
• 4894-75-1 1-phenyl-4-cyclohexanone 
• 5122-94-1 4-biphenylboronic acid 
• 580-51-8 [1,1'-biphenyl]-3-ol 
• 1344113-40-1 C₂₀H₂₈O₂Si 
• 854021-41-3 2-biphenyl-3-yloxy-5-nitro-benzophenone 
• 39811-18-2 2-biphenyl-4-yloxy-5-nitro-benzophenone 
• 3506-36-3 3-dimethylaminopropiophenone 
• 56-23-5 tetrachloromethane 
• 92-04-6 2-chloro-4-phenylphenol 
• 7732-18-5 water 
• 7758-99-8 copper(II) sulfate 
• 885-82-5 4-phenyl-2-nitrophenol 
• 177762-44-6 1-[3-(Fluoro-dimethyl-silanyl)-biphenyl-4-yl]-ethanone 

Downstream Products

• 17189-95-6 4-phenyl-1,2-benzoquinone 
• 98980-45-1 3,8-dimethyl-5-phenyl-2,3,4,7,8,9-hexahydro-benzo[1,2-e;4,3-e']bis[1,3]oxazine 
• 92850-72-1 3-methyl-6-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazin-8-ol 
• 1043534-02-6 2-(7-phenyl-2,3-dihydro-1,4-benzodioxin-2-yl)-4,5-dihydro-1H-imidazole 
• 1043533-99-8 2-(6-phenyl-2,3-dihydro-1,4-benzodioxin-2-yl)-4,5-dihydro-1H-imidazole 
• 37055-80-4 4-methoxy-[1,1'-biphenyl]-3-ol 

Relevant articles and documents

Altering 2-Hydroxybiphenyl 3-Monooxygenase Regioselectivity by Protein Engineering for the Production of a New Antioxidant

2-Hydroxybiphenyl 3-monooxygenase is a flavin-containing NADH-dependent aromatic hydroxylase that oxidizes a broad range of 2-substituted phenols. In order to modulate its activity and selectivity, several residues in the active site pocket were investigated by saturation mutagenesis. Variant M321A demonstrated altered regioselectivity by oxidizing 3-hydroxybiphenyl for the first time, thus enabling the production of a new antioxidant, 3,4-dihydroxybiphenyl, with similar ferric reducing capacity to the well-studied piceatannol. The crystal structure of M321A was determined (2.78 ?), and molecular docking of the 3-substituted phenol provided a rational explanation for the altered regioselectivity. Furthermore, HbpA was found to possess pro-S enantioselectivity towards the production of several chiral sulfoxides, whereas variant M321F exhibited improved enantioselectivity. Based on the biochemical characterization of several mutants, it was suggested that Trp97 stabilized the substrate in the active site, Met223 was involved in NADH entrance or binding to the active site, and Pro320 might facilitate FAD movement.

Conversion of Simple Cyclohexanones into Catechols

A novel I2-catalyzed direct conversion of cyclohexanones to substituted catechols under mild and simple conditions has been described. This novel transformation is remarkable with the multiple oxygenation and dehydrogenative aromatization processes enabled just by using DMSO as the solvent, oxidant, and oxygen source. This metal-free and simple system demonstrates a versatile protocol for the synthesis of highly valuable substituted catechols and therefore streamlines the synthesis and modification of biologically important molecules for drug discovery.

Synthesis of catechols from phenols via Pd-catalyzed silanol-directed C-H oxygenation

A silanol-directed, Pd-catalyzed C-H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon-protected catechol. A routine desilylation of the silacyle with TBAF uncovers the catechol product.