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
• Article Data: 7

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

Hydroxydi-p-tolylborane is a building block used as a reactant in the nickel-catalyzed cross-coupling of diarylborinic acids with aryl chlorides.

Upstream product

• 4294-57-9 para-methylphenylmagnesium bromide 
• 90000-20-7 (dipropylamino)borane 
• 624-31-7 4-tolyl iodide 
• 7732-18-5 water 
• 18494-92-3 (diethylamino)borane 
• 121-43-7 Trimethyl borate 
• 5419-55-6 Triisopropyl borate 
• 3578-49-2 (4-CH₃C₆H₄)2B-N(i-C₃H₇)2 
• 22092-92-8 diisopropopylaminoborane 
• 106-43-4 para-chlorotoluene 
• 106-38-7 para-bromotoluene 
• 19565-45-8 2-(di-p-tolyl-boranyloxy)-ethylamine 
• 16500-38-2 tris(isobutyloxy) boroxine 
• 102-24-9 cyclotriboric acid trimethyl ester 

Downstream Products

• 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)] 
• 114772-53-1 2-Cyano-4'-methylbiphenyl 
• 23886-71-7 4-methoxy-4'-methylbenzophenone 
• 13365-62-3 furan-2-yl-p-tolyl-methanone 
• 6933-25-1 2-thienyl 4-methylphenyl ketone 
• 14802-30-3 (E)-1-(4-methylphenyl)-3-phenyl-2-propen-1-one 
• 5012-90-8 4-methylphenyl phenethyl ketone 
• 860756-49-6 1-(p-tolyl)octadecan-1-one 
• 2789-44-8 cyclohexyl(p-tolyl)methanone 
• 1140-16-5 (2-methylphenyl)(4-methylphenyl)methanone 
• 134-84-9 4-Methylbenzophenone 
• 530-46-1 4-fluoro-4'-methylbenzophenone 

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.

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.

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.