635305-47-4

Usage

Uses

Used in Organic Synthesis:
3-Chlorophenylboronic acid, pinacol ester is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds in organic synthesis reactions. Its stability and reactivity make it a valuable component in creating complex organic molecules.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
In the pharmaceutical industry, 3-chlorophenylboronic acid, pinacol ester is used as a key reagent in Suzuki-Miyaura cross-coupling reactions. These reactions are crucial for the production of various pharmaceuticals, as they facilitate the formation of carbon-carbon bonds between aryl and vinyl halides or triflates with arylboronic acids.
Used in Agrochemicals Production:
3-Chlorophenylboronic acid, pinacol ester is utilized in the agrochemical industry for the synthesis of various agrochemicals. Its application in Suzuki-Miyaura cross-coupling reactions aids in the production of compounds with pesticidal properties, contributing to the development of effective crop protection agents.
Used in Materials Science:
In the field of materials science, 3-chlorophenylboronic acid, pinacol ester is used as a building block in the synthesis of new materials. Its potential as a precursor in the development of advanced materials makes it a valuable tool for researchers working on innovative material designs with specific properties for various applications.
Used in the Development of New Materials:
3-Chlorophenylboronic acid, pinacol ester has shown potential as a tool in the development of new materials. Its unique properties and reactivity in organic synthesis reactions allow researchers to explore its use in creating novel materials with tailored characteristics for specific industries and applications.

InChI:InChI=1/C12H16BClO2/c1-11(2)12(3,4)16-13(15-11)9-6-5-7-10(14)8-9/h5-8H,1-4H3

Upstream product

• 25240-59-9 pinacolboronic acid 
• 86364-03-6 3-chloro-1-trifluoromethanesulfonyloxybenzene 
• 108-43-0 3-monochlorophenol 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 63503-60-6 3-chlorophenylboronic acid 
• 745783-97-5 triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 108-90-7 chlorobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 108-42-9 3-chloro-aniline 
• 73183-34-3 bis(pinacol)diborane 
• 108-37-2 1-bromo-3-chlorobenzene 
• 625-99-0 3-iodochlorobenzene 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 63591-88-8 1,3-dioxoisoindolin-2-yl 3-chlorobenzoate 

Downstream Products

• 108-37-2 1-bromo-3-chlorobenzene 
• 893734-67-3 5-(3-Chloro-phenyl)-nicotinic acid methyl ester 
• 1256781-63-1 2-(2-bromo-5-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1334531-95-1 methyl 2-(3-chlorophenyl)-2-(4-chlorophenyl)-3-phenylpropanoate 
• 1401732-45-3 5-(3-chlorophenyl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine 
• 108-43-0 3-monochlorophenol 
• 7408-32-4 2,3-bis(3-chlorophenyl)quinoxaline 
• 625-98-9 3-chlorofluorobenzene 
• 535-80-8 3-chlorobenzoate 

Relevant academic research and scientific papers

Mono-Phosphine Metal-Organic Framework-Supported Cobalt Catalyst for Efficient Borylation Reactions

We report a metal-organic framework (MOF) supported monoligated phosphine-cobalt complex, which is an active heterogeneous catalyst for aromatic C?H borylation and alkene hydroboration. The mono(phosphine)-Co catalyst (MOF?P?Co) was prepared by metalation of a porous triarylphosphine-functionalized MOF (MOF?P) with CoCl2 followed by activation with NaEt3BH. The MOF catalyst has a broad substrate scope with excellent functional group tolerance to afford arene- and alkyl-boronate esters in excellent yields and selectivity. MOF?P?Co gave a turnover number (TON) of 30,000 and could be recycled and reused at least 13 times in arene C?H borylation. Importantly, the attempt to prepare the homogeneous control (Ph3P?Co) using triphenylphosphine was unsuccessful due to the facile disproportionation reactions or intermolecular ligand exchanges in the solution. In contrast, the site isolation of the active mono(phosphine)-Co species within the MOF affords the robust and coordinatively unsaturated metal complexes, allowing to explore their catalytic properties and the reaction mechanism.

Photochemical and electrochemical C-N borylation of arylhydrazines

The C-N borylation of arylhydrazine hydrochlorides with bis(pinacolato)diboron was achieved under photochemical and electrochemical conditions, respectively. This novel and scalable transformation provides two efficient and mild transition-metal-free synt

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.

Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron

The desulfitative borylation reaction of sodium arylsulfinates with bis(pinacolato)diboron or bis(neopentylglycolato)diboron under palladium catalysis has been developed, allowing selective C-B bond formation to give arylboronates with a range of functional groups in moderate to good yields under mild reaction conditions. A gram-scale preparation as well as the cascade Suzuki-Miyaura cross-coupling of arylboronates demonstrated the potential practical utility in organic synthesis.

Controllable factors of supported IR complex catalysis for aromatic C?H borylation

We have developed a catalyst in which an Ir complex and organic functionalities are coimmobilized on the silica surface. The catalytic activity for aromatic C?H borylation was significantly affected by (i) the linker length of the Ir?bipyridine complex, (ii) the coimmobilized organic functionality, and (iii) the substituents on the aromatic substrate compounds. The fine-tuned supported catalyst showed higher activity than the homogeneous Ir?bipyridine complex when using a specific substrate such as benzonitrile. We elucidated this property by conducting solid-state NMR, FT-IR, XAFS, and in situ FT-IR analysis.

Discovery of S64315, a Potent and Selective Mcl-1 Inhibitor

Myeloid cell leukemia 1 (Mcl-1) has emerged as an attractive target for cancer therapy. It is an antiapoptotic member of the Bcl-2 family of proteins, whose upregulation in human cancers is associated with high tumor grade, poor survival, and resistance to chemotherapy. Here we report the discovery of our clinical candidate S64315, a selective small molecule inhibitor of Mcl-1. Starting from a fragment derived lead compound, we have conducted structure guided optimization that has led to a significant (3 log) improvement of target affinity as well as cellular potency. The presence of hindered rotation along a biaryl axis has conferred high selectivity to the compounds against other members of the Bcl-2 family. During optimization, we have also established predictive PD markers of Mcl-1 inhibition and achieved both efficient in vitro cell killing and tumor regression in Mcl-1 dependent cancer models. The preclinical candidate has drug-like properties that have enabled its development and entry into clinical trials.

Visible-Light-Induced Ni-Catalyzed Radical Borylation of Chloroarenes

A highly selective and general photoinduced C-Cl borylation protocol that employs [Ni(IMes)2] (IMes = 1,3-dimesitylimidazoline-2-ylidene) for the radical borylation of chloroarenes is reported. This photoinduced system operates with visible light (400 nm) and achieves borylation of a wide range of chloroarenes with B2pin2 at room temperature in excellent yields and with high selectivity, thereby demonstrating its broad utility and functional group tolerance. Mechanistic investigations suggest that the borylation reactions proceed via a radical process. EPR studies demonstrate that [Ni(IMes)2] undergoes very fast chlorine atom abstraction from aryl chlorides to give [NiI(IMes)2Cl] and aryl radicals. Control experiments indicate that light promotes the reaction of [NiI(IMes)2Cl] with aryl chlorides generating additional aryl radicals and [NiII(IMes)2Cl2]. The aryl radicals react with an anionic sp2-sp3 diborane [B2pin2(OMe)]- formed from B2pin2 and KOMe to yield the corresponding borylation product and the [Bpin(OMe)]?- radical anion, which reduces [NiII(IMes)2Cl2] under irradiation to regenerate [NiI(IMes)2Cl] and [Ni(IMes)2] for the next catalytic cycle.

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.

Undirected ortho-selectivity in C–H borylation of arenes catalyzed by NHC platinum(0) complexes

Borylation of arenes with bis(pinacolato)diboron catalyzed by sterically encumbered NHC platinum complexes proceeds predominantly at ortho-position even in the absence of a directing group (o: m: p ratio up to 10: 3: 1). The similar borylation with pinacolborane would proceed less selectively.

Rh-Catalyzed Base-Free Decarbonylative Borylation of Twisted Amides

We report the rhodium-catalyzed base-free decarbonylative borylation of twisted amides. The synthesis of versatile arylboronate esters from aryl twisted amides is achieved via decarbonylative rhodium(I) catalysis and highly selective N-C(O) insertion. The method is notable for a very practical, additive-free Rh(I) catalyst system. The method shows broad functional group tolerance and excellent substrate scope, including site-selective decarbonylative borylation/Heck cross-coupling via divergent N-C/C-Br cleavage and late-stage pharmaceutical borylation.