66117-64-4

Basic information

• Product Name: BIS(4-TOLYL)BORONIC ACID
• Synonyms: Borinic acid, bis(4-methylphenyl)-;Borinic acid, B,B-bis(4-methylphenyl)-
• CAS NO: 66117-64-4
• Molecular Formula: C₁₄H₁₅BO
• Molecular Weight: 210.083
• Mol File: 66117-64-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BIS(4-TOLYL)BORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(4-TOLYL)BORONIC ACID(66117-64-4)
• EPA Substance Registry System: BIS(4-TOLYL)BORONIC ACID(66117-64-4)

Safety Data

• Hazardous Substances Data: 66117-64-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
BIS(4-TOLYL)BORONIC ACID is used as a reactant in the nickel-catalyzed cross-coupling of diarylborinic acids with aryl chlorides. This reaction is crucial for the formation of carbon-carbon bonds, which are essential in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, BIS(4-TOLYL)BORONIC ACID is utilized as a key intermediate in the synthesis of various drug molecules. Its ability to form stable boron-containing compounds allows for the development of new drugs with improved pharmacological properties and therapeutic effects.
Used in Materials Science:
BIS(4-TOLYL)BORONIC ACID is also employed in the development of advanced materials, such as polymers, coatings, and composites. Its unique chemical properties enable the creation of materials with enhanced performance characteristics, such as improved thermal stability, mechanical strength, and chemical resistance.
Overall, BIS(4-TOLYL)BORONIC ACID is a valuable compound with diverse applications across various industries, including chemical synthesis, pharmaceuticals, and materials science. Its versatility and ability to form stable boron-containing compounds make it an essential component in the development of new and innovative products.

Upstream product

• 688-74-4 boric acid tributyl ester 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 102-24-9 cyclotriboric acid trimethyl ester 
• 16500-38-2 tris(isobutyloxy) boroxine 
• 106-38-7 para-bromotoluene 
• 22092-92-8 diisopropopylaminoborane 
• 106-43-4 para-chlorotoluene 
• 624-31-7 4-tolyl iodide 
• 3578-49-2 (4-CH₃C₆H₄)2B-N(i-C₃H₇)2 
• 7732-18-5 water 
• 5419-55-6 Triisopropyl borate 
• 121-43-7 Trimethyl borate 
• 90000-20-7 (dipropylamino)borane 
• 18494-92-3 (diethylamino)borane 

Downstream Products

• 5720-05-8 4-methylphenylboronic acid 
• 19565-45-8 2-(di-p-tolyl-boranyloxy)-ethylamine 
• 276671-82-0 [(H₃C)Co((ONC(CH₃)C(CH₃)NOB(C₆H₄CH₃)2)2)(C₃H₃N₂CH₃)] 
• 276671-84-2 [(C₆H₅)Co((ONC(CH₃)C(CH₃)NOB(C₆H₄CH₃)2)2)(C₃H₃N₂CH₃)] 
• 276671-69-3 [(CH₃)Co((ONC(CH₃)C(CH₃)NOB(C₆H₄CH₃)2)2)(H₂O)] 
• 114772-53-1 2-Cyano-4'-methylbiphenyl 
• 1414261-77-0 1-bromo-4-(1-p-tolylethyl)benzene 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 
• 53040-92-9 4-(4-tolyl)anisole 
• 1204-78-0 4-(4-methylphenyl)aniline 
• 1204-43-9 2-(4-methylphenyl)aniline 
• 50670-50-3 p-(p-tolyl)benzonitrile 
• 133909-96-3 4'-methyl-[1,1'-biphenyl]-3-carbonitrile 
• 49742-56-5 methyl 4-(4-tolyl)benzoate 

Relevant articles and documents

Palladium-catalyzed B-diarylation of diethylaminoborane for the synthesis of diarylborinic acids

The palladium-catalyzed synthesis of diarylborinic acid derivatives by intermolecular cross-coupling between aryl iodides and (amino)dihydrideborane is reported. The key to success of the reaction is the use of a less bulky diethylaminoborane reagent, which facilitates the second B-arylation.

Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates

Organozinc pivalates, a recently developed air- and moisture-stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki-Miyaura type cross-coupling reactions to produce biaryls in high yields.

Borinic Acids via Direct Arylation of Amine-Borane Complexes: An Air- and Water-Stable Boron Source

A synthesis of borinic acids and borinates was optimized using amine-borane complexes as a water and air insensitive borylating agent. The reaction operates under convenient conditions using a non-cryogenic temperature and with no flash chromatography, and it gives no boron impurities. The reaction proceeds through a tandem dehydrogenation-double addition mechanism.

Synthesis of Borinic Acids and Borinate Adducts Using Diisopropylaminoborane

In situ formation of aryl Grignard under Barbier condition and diisopropylaminoborane as boron source allows a complete control of the addition onto the boron electrophile. Analytically pure borinic acid derivatives were produced at the gram scale without column chromatography and isolated as borinates adducts, with ethanolamine or 8-hydroxyquinoline, after workup.

Design, synthesis and pharmacological characterization of analogs of 2-aminoethyl diphenylborinate (2-APB), a known store-operated calcium channel blocker, for inhibition of TRPV6-mediated calcium transport

2-Aminoethyl diphenylborinate (2-APB) is a known modulator of the IP 3 receptor, the calcium ATPase SERCA, the calcium release-activated calcium channel Orai and TRP channels. More recently, it was shown that 2-APB is an efficient inhibitor of the epithelial calcium channel TRPV6 which is overexpressed in prostate cancer. We have conducted a structure-activity relationship study of 2-APB congeners to understand their inhibitory mode of action on TRPV6. Whereas modifying the aminoethyl moiety did not significantly change TRPV6 inhibition, substitution of the phenyl rings of 2-APB did. Our data show that the diaryl borinate moiety is required for biological activity and that the substitution pattern of the aryl rings can influence TRPV6 versus SOCE inhibition. We have also discovered that 2-APB is hydrolyzed and transesterified within minutes in solution.

Cross-coupling of diarylborinic acids and anhydrides with arylhalides catalyzed by a phosphite/N-heterocyclic carbene co-supported palladium catalyst system

A highly efficient cross-coupling of diarylborinic acids and anhydrides with aryl chlorides and bromides has been effected by using a palladium catalyst system co-supported by a strong σ-donor N-heterocyclic carbene (NHC), N,N′-bis(2,6-diisopropylphenyl) imidazol-2-ylidene, and a strong π-acceptor phosphite, triphenylphosphite, in tert-BuOH in the present of K3PO4·3H2O. Unsymmetrical biaryls with a variety of functional groups could be obtained in good to excellent yields using as low as 0.01, 0.2-0.5, and 1 mol % palladium loadings for aryl bromides and activated and deactivated aryl chlorides, respectively, under mild conditions. A ligand synergy between the σ-donor NHC and the π-acceptor phosphite in the Pd/NHC/P(OPh)3 catalytic system has been proposed to be responsible for the high efficacy to arylchlorides in the cross-coupling. A scalable and economical process has therefore been developed for synthesis of Sartan biphenyl from the Pd/NHC/P(OPh)3 catalyzed cross-coupling of di(4-methylphenyl)borinic acid with 2-chlorobenzonitrile.

Palladium-catalyzed cross-coupling reaction of potassium diaryldifluoroborates with aryl halides

The catalytic cross-coupling reaction of potassium diaryldifluoroborates with aryl halides proceeds to afford the biphenyls in good yields. These salts on an arylation reagent were readily prepared via a protocol of the Grignard method and transformation to potassium salts. Two aryl groups of these salts were efficiently transferred in the Suzuki-Miyaura reaction.