105904-28-7

Basic information

• Product Name: (2-bromophenyl)(3-chlorophenyl)methanol
• Synonyms: (2-bromophenyl)(3-chlorophenyl)methanol
• CAS NO: 105904-28-7
• Molecular Weight: 297.579
• Mol File: 105904-28-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (2-bromophenyl)(3-chlorophenyl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2-bromophenyl)(3-chlorophenyl)methanol(105904-28-7)
• EPA Substance Registry System: (2-bromophenyl)(3-chlorophenyl)methanol(105904-28-7)

Safety Data

• Hazardous Substances Data: 105904-28-7(Hazardous Substances Data)

Usage

Description

(2-bromophenyl)(3-chlorophenyl)methanol is a chiral chemical compound composed of two benzene rings, one featuring a bromine and a phenol group attached to a carbon atom, and the other with a chlorine and a phenol group attached to another carbon atom. Its unique structure allows it to exist in two non-superimposable mirror image forms, making it a valuable compound in pharmaceuticals and organic synthesis.

Uses

Used in Pharmaceutical Industry:
(2-bromophenyl)(3-chlorophenyl)methanol is used as an intermediate in the synthesis of various pharmaceutical compounds for its unique chiral properties, which can influence the activity and selectivity of the resulting drugs.
Used in Organic Synthesis:
In the field of organic synthesis, (2-bromophenyl)(3-chlorophenyl)methanol serves as a key building block for the creation of complex organic molecules, taking advantage of its reactive bromine and chlorine substituents to facilitate various chemical reactions.
It is important to handle (2-bromophenyl)(3-chlorophenyl)methanol with care due to its potential hazardous properties, ensuring safety in both production and application processes.

Upstream product

• 6630-33-7 ortho-bromobenzaldehyde 
• 36229-42-2 (3-chlorophenyl)magnesium bromide 
• 7154-66-7 2-bromobenzoic acid chloride 
• 108-37-2 1-bromo-3-chlorobenzene 
• 99586-30-8 2-bromo-3'-chlorobenzophenone 

Downstream Products

• 2523-44-6 2-chloro-9H-fluorene 
• 28322-03-4 4-chloro-9H-fluorene 
• 105901-07-3 1-bromo-2-(3-chlorobenzyl)benzene 

Relevant articles and documents

Au-catalyzed biaryl coupling to generate 5- to 9-membered rings: Turnover-limiting reductive elimination versus π-complexation

The intramolecular gold-catalyzed arylation of arenes by aryl-trimethylsilanes has been investigated from both mechanistic and preparative aspects. The reaction generates 5- to 9-membered rings, and of the 44 examples studied, 10 include a heteroatom (N, O). Tethering of the arene to the arylsilane provides not only a tool to probe the impact of the conformational flexibility of Ar-Au-Ar intermediates, via systematic modulation of the length of aryl-aryl linkage, but also the ability to arylate neutral and electron-poor arenes-substrates that do not react at all in the intermolecular process. Rendering the arylation intramolecular also results in phenomenologically simpler reaction kinetics, and overall these features have facilitated a detailed study of linear free energy relationships, kinetic isotope effects, and the first quantitative experimental data on the effects of aryl electron demand and conformational freedom on the rate of reductive elimination from diaryl-gold(III) species. The turnover-limiting step for the formation of a series of fluorene derivatives is sensitive to the reactivity of the arene and changes from reductive elimination to π-complexation for arenes bearing strongly electron-withdrawing substituents (σ > 0.43). Reductive elimination is accelerated by electron-donating substituents (ρ = -2.0) on one or both rings, with the individual σ-values being additive in nature. Longer and more flexible tethers between the two aryl rings result in faster reductive elimination from Ar-Au(X)-Ar and lead to the π-complexation of the arene by Ar-AuX2 becoming the turnover-limiting step.

Efficient palladium-catalyzed C(sp2)-H activation towards the synthesis of fluorenes

A facile protocol for the synthesis of fluorene derivatives has been developed through palladium-catalyzed cyclization of 2′-halo-diarylmethanes via activation of arylic C-H bonds. The reactions occurred smoothly and allowed both electron-rich and electron-deficient substrates to convert into their corresponding fluorenes in good to excellent yields. Studies revealed that this Pd-catalyzed cyclization was also available for the substrates of 2′-chloro-diarylmethanes and no catalyst poisoning occurred for 2′-iodo-diphenylmethane.

Electrophilic peptide analogs as inhibitors of trypsin-like enzymes

This invention relates to electrophilic dipeptide analogs conjugated to an N,N-disubstituted alpha -amino acid as inhibitors of trypsin-like serine protease enzymes.