85-97-2

Basic information

• Product Name: 3-chloro[1,1'-biphenyl]-2-ol
• Synonyms: 6-Chloro-2-phenylphenol;2-phenyl-6-chlorophenol;2-Chloro-6-phenylphenol;2-Hydroxy-3-chlorobiphenyl;3-Chlorobiphenyl-2-ol
• CAS NO: 85-97-2
• Molecular Formula: C12H9ClO
• Molecular Weight: 204.65226
• EINECS: 201-644-7
• Mol File: 85-97-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 6°C
• Boiling Point: 293.89°C (rough estimate)
• Appearance: /
• Density: 1.2400
• Refractive Index: 1.6237 (estimate)
• PKA: 8.52±0.10(Predicted)
• CAS DataBase Reference: 3-chloro[1,1'-biphenyl]-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro[1,1'-biphenyl]-2-ol(85-97-2)
• EPA Substance Registry System: 3-chloro[1,1'-biphenyl]-2-ol(85-97-2)

Safety Data

• Hazardous Substances Data: 85-97-2(Hazardous Substances Data)

Usage

General Description

3-Chloro[1,1'-biphenyl]-2-ol, also known as 2-chloro-3-hydroxybiphenyl, is an organic compound with the chemical formula C12H9ClO. It is a chlorinated derivative of biphenyl and has a hydroxyl group attached to the second carbon of the biphenyl structure. This chemical is used as an intermediate in the synthesis of pharmaceuticals, dyes, and other organic compounds. It is also used as a reagent in organic synthesis and biochemical research. 3-Chloro[1,1'-biphenyl]-2-ol is a white solid with a slightly sweet odor and has low water solubility. It is important to handle this chemical with care as it can be harmful if ingested, inhaled, or in contact with the skin.

InChI:InChI=1/C12H9ClO/c13-11-8-4-7-10(12(11)14)9-5-2-1-3-6-9/h1-8,14H

Upstream product

• 95-57-8 2-monochlorophenol 
• 100-34-5 benzene diazonium chloride 
• 90-43-7 2-Phenylphenol 
• 7782-50-5 chlorine 
• 7705-08-0 iron(III) chloride 
• 591-50-4 iodobenzene 
• 1033783-04-8 potassium (3-chloro-2-hydroxyphenyl)trifluoroborate 
• 344332-09-8 C₁₂H₁₈ClOP 

Downstream Products

• 1133-63-7 3-phenylcatechol 
• 90-43-7 2-Phenylphenol 
• 21419-69-2 6-Chlor-phenyl-phenoxyessigsaeure 
• 119338-73-7 [2-(3-chloro-biphenyl-2-yloxy)-ethyl]-dimethyl-tetradecyl-ammonium; bromide 

Relevant articles and documents

Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines through a Lewis Basic Selenoether Catalyst

We report a highly efficient ortho-selective electrophilic chlorination of phenols utilizing a Lewis basic selenoether catalyst. The selenoether catalyst resulted in comparable selectivities to our previously reported bis-thiourea ortho-selective catalyst, with a catalyst loading as low as 1%. The new catalytic system also allowed us to extend this chemistry to obtain excellent ortho-selectivities for unprotected anilines. The selectivities of this reaction are up to >20:1 ortho/para, while the innate selectivities for phenols and anilines are approximately 1:4 ortho/para. A series of preliminary studies revealed that the substrates require a hydrogen-bonding moiety for selectivity.

The Catalyst-Controlled Regiodivergent Chlorination of Phenols

Different catalysts are demonstrated to overcome or augment a substrate's innate regioselectivity. Nagasawa's bis-thiourea catalyst was found to overcome the innate para-selectivity of electrophilic phenol chlorination, yielding ortho-chlorinated phenols that are not readily obtainable via canonical electrophilic chlorinations. Conversely, a phosphine sulfide derived from 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was found to enhance the innate para-preference of phenol chlorination.