765917-27-9

Basic information

• Product Name: 4-chloro-2-fluorophenylboronic aicd, pinacol ester
• Synonyms: 4-chloro-2-fluorophenylboronic aicd, pinacol ester;2-(4-Chloro-2-fluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane;4-Chloro-2-fluorobenzeneboronic acid pinacol ester, 96%;2-(4-Chloro-2-fluorophenyl)
• CAS NO: 765917-27-9
• Molecular Formula: C₁₂H₁₅BClFO₂
• Molecular Weight: 274.5239832
• Mol File: 765917-27-9.mol

Chemical Properties

• Appearance: /Solid
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-chloro-2-fluorophenylboronic aicd, pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-2-fluorophenylboronic aicd, pinacol ester(765917-27-9)
• EPA Substance Registry System: 4-chloro-2-fluorophenylboronic aicd, pinacol ester(765917-27-9)

Safety Data

• Hazardous Substances Data: 765917-27-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-chloro-2-fluorophenylboronic acid, pinacol ester is used as a building block for the synthesis of various organic compounds due to its reactivity and unique properties. It allows chemists to create complex molecules with specific functional groups, facilitating the development of new chemical entities.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4-chloro-2-fluorophenylboronic acid, pinacol ester is employed as a key intermediate in the synthesis of pharmaceuticals. Its unique structure and reactivity enable the creation of novel drug candidates with potential therapeutic applications.
Used in Agrochemical Development:
4-chloro-2-fluorophenylboronic acid, pinacol ester is also utilized in the development of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds can lead to the discovery of more effective and environmentally friendly products for agricultural use.
Used in Research and Development:
4-chloro-2-fluorophenylboronic aicd, pinacol ester is a valuable tool for researchers in academia and industry, as it can be used to study the properties and reactivity of boronic acid derivatives. It contributes to the advancement of chemical knowledge and the development of innovative applications in various fields.

Upstream product

• 625-98-9 3-chlorofluorobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1073-06-9 3-fluorobromobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 765917-28-0 3-(4-chloro-2-fluorophenyl)-5-[4-fluoro-3-(3-fluoropyridin-2-yl)phenyl]-[1,2,4]triazine 

Relevant articles and documents

Direct C?H Borylation of Arenes Catalyzed by Saturated Hydride-Boryl-Iridium-POP Complexes: Kinetic Analysis of the Elemental Steps

The saturated trihydride IrH3{κ3-P,O,P-[xant(PiPr2)2]} (1; xant(PiPr2)2=9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene) activates the B?H bond of two molecules of pinacolborane (HBpin) to give H2, the hydride-boryl derivatives IrH2(Bpin){κ3-P,O,P-[xant(PiPr2)2]} (2) and IrH(Bpin)2{κ3-P,O,P-[xant(PiPr2)2]} (3) in a sequential manner. Complex 3 activates a C?H bond of two molecules of benzene to form PhBpin and regenerates 2 and 1, also in a sequential manner. Thus, complexes 1, 2, and 3 define two cycles for the catalytic direct C?H borylation of arenes with HBpin, which have dihydride 2 as a common intermediate. C?H bond activation of the arenes is the rate-determining step of both cycles, as the C?H oxidative addition to 3 is faster than to 2. The results from a kinetic study of the reactions of 1 and 2 with HBpin support a cooperative function of the hydride ligands in the B?H bond activation. The addition of the boron atom of the borane to a hydride facilitates the coordination of the B?H bond through the formation of κ1- and κ2-dihydrideborate intermediates.

C-H Borylation Catalysts that Distinguish between Similarly Sized Substituents like Fluorine and Hydrogen

By modifying ligand steric and electronic profiles it is possible to C-H borylate ortho or meta to substituents in aromatic and heteroaromatic compounds, where steric differences between accessible C-H sites are small. Dramatic effects on selectivities between reactions using B2pin2 or 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin) are described for the first time. Judicious ligand and borane combinations give highly regioselective C-H borylations on substrates where typical borylation protocols afford poor selectivities.

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.

Transition metal-free synthesis of pinacol arylboronate: Regioselective boronation of 1,3-disubstituted benzenes

The regioselective synthesis of pinacol arylboronate has been achieved from 1,3-disubstituted benzene through directed ortho-metallation (DoM)-borylation sequence. A wide range of substituents and borylating reagents were investigated. In situ lithiation and subsequent boronation predominantly occurred at the ortho-position to afford the desired products in moderate yields. CSIRO 2014.