627525-83-1

Basic information

• Product Name: 4-Chloro-3-fluorophenylboronic acid pinacol ester
• Synonyms: 4-Chloro-3-fluorophenylboronic acid pinacol ester;2-(4-chloro-3-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 627525-83-1
• Molecular Formula: C12H17BClFO3
• Molecular Weight: 274.5239832
• Mol File: 627525-83-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Chloro-3-fluorophenylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-3-fluorophenylboronic acid pinacol ester(627525-83-1)
• EPA Substance Registry System: 4-Chloro-3-fluorophenylboronic acid pinacol ester(627525-83-1)

Safety Data

• Hazardous Substances Data: 627525-83-1(Hazardous Substances Data)

Usage

General Description

4-Chloro-3-fluorophenylboronic acid pinacol ester is a chemical compound that is used in organic synthesis and pharmaceutical research. It is a boronic acid ester, which means it contains a boron atom attached to a phenyl ring and two pinacol ester groups. 4-Chloro-3-fluorophenylboronic acid pinacol ester is particularly valuable in Suzuki-Miyaura cross-coupling reactions, where it serves as a versatile coupling partner for the introduction of the 4-chloro-3-fluorophenyl group into various organic molecules. Additionally, the pinacol ester functionality can be selectively cleaved under mild conditions to reveal the free boronic acid, providing further synthetic utility. Overall, 4-Chloro-3-fluorophenylboronic acid pinacol ester is an important building block in the synthesis of diverse chemical compounds and is a valuable tool for researchers in the field of organic chemistry and pharmaceutical development.

Upstream product

• 60811-18-9 2-chloro-5-bromofluorobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 348-51-6 1-chloro-2-fluorobenzene 
• 1359224-18-2 Me₂NTol*BCl₃ 

Relevant articles and documents

Ligand-Enabled, Iridium-Catalyzed ortho-Borylation of Fluoroarenes

A terpyridine derivative and an iridium complex catalyze the C-H borylation of a stoichiometric amount of a fluoroarene with high ortho-selectivity and tolerance of functional groups such as bromide, chloride, ester, ketone, amine, and in situ-borylated hydroxyl. Complex drug molecules such as haloperidol can be selectively borylated ortho to the F atom. The terpyridine ligand undergoes rollover cyclometalation to produce an N,N,C-coordinated iridium complex, which may either selectively borylate the fluoroarene by itself or undergo reductive elimination to produce a borylated ligand.

Regioselective electrophilic borylation of haloarenes

Haloarenes undergo direct borylation using amine:BCl3:AlCl3 in the ratio of 1:1:2. After esterification the pinacol boronate esters are isolated in good yield with regioselectivity controlled by steric and electronic effects.

Substituted imidazol-pyridazine derivatives

The present invention relates to compounds of formula wherein A is an unsubstituted or substituted cyclic group; and R is hydrogen or lower alkyl; or a pharmaceutically acceptable acid addition salt thereof. These compounds are NMDA NR-2B receptor subtype specific blockers and are useful in the treatment of neurodegeneration, depression and pain.