635305-46-3

Basic information

• Product Name: 3-Chloro-4-fluorophenylboronic acid pinacol ester
• Synonyms: 3-Chloro-4-fluorophenylboronic acid pinacol ester
• CAS NO: 635305-46-3
• Molecular Formula: C12H17BClFO3
• Molecular Weight: 274.5239832
• Mol File: 635305-46-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 316.2±32.0 °C(Predicted)
• Appearance: /
• Density: 1.16±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 3-Chloro-4-fluorophenylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-4-fluorophenylboronic acid pinacol ester(635305-46-3)
• EPA Substance Registry System: 3-Chloro-4-fluorophenylboronic acid pinacol ester(635305-46-3)

Safety Data

• Hazardous Substances Data: 635305-46-3(Hazardous Substances Data)

Usage

Description

3-Chloro-4-fluorophenylboronic acid pinacol ester is a boronic acid derivative featuring a 3-chloro-4-fluorophenyl group attached to a boronic acid pinacol ester moiety. It is a versatile chemical compound widely used in organic synthesis for the development of pharmaceuticals, agrochemicals, and materials science.

Uses

Used in Pharmaceutical Industry:
3-Chloro-4-fluorophenylboronic acid pinacol ester is used as a building block for the synthesis of various biologically active compounds, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
3-Chloro-4-fluorophenylboronic acid pinacol ester serves as an intermediate in the creation of agrochemicals, playing a crucial role in the synthesis of pesticides and other agricultural chemicals to improve crop protection and yield.
Used in Materials Science:
3-Chloro-4-fluorophenylboronic acid pinacol ester is utilized in the synthesis of advanced materials with specific properties, such as conductivity, strength, or light absorption, for applications in various industries.
Used in Metal-Catalyzed Coupling Reactions:
Due to its ability to form stable complexes with a wide range of metal ions, 3-Chloro-4-fluorophenylboronic acid pinacol ester is used as a reagent in metal-catalyzed coupling reactions, facilitating the formation of carbon-carbon and carbon-heteroatom bonds in organic synthesis.
Overall, 3-Chloro-4-fluorophenylboronic acid pinacol ester is an essential reagent in organic chemistry with diverse applications across the fields of chemical research and development.

Upstream product

• 348-51-6 1-chloro-2-fluorobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 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.

Chemoselective coupling of 1,1-bis[(pinacolato)boryl]alkanes for the transition-metal-frec borylation of aryl and vinyl halides: A combined experimental and theoretical investigation

A new transition-metal-frec borylation of aryl and vinyl halides using l,l-bis[(pinacolato)boryl]alkanes as boron sources is described. In this transformation one of the boron groups from 1,1-bis[(pinacolato)boryl]alkanes is selectively transferred to aryl and vinyl halides in the presence of sodium tert-butoxide as the only activator to form organoboronate esters. Under the developed borylation conditions, a broad range of organohalides are borylated with excellent chemo-selectivity and functional group compatibility, thus offering a rare example of a transition-metal-frec borylation protocol. Experimental and theoretical studies have becn performed to elucidate the reaction mechanism, revealing the unusual formation of Lewis acid/base adduct betwecn organohalides and α-borylcarbanion, generated in situ from the reaction of l,l-bis[(pinacolato)boryl]alkanes with an alkoxide base, to facilitate the borylation reactions.

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.