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Benzylboronic acid pinacol ester is an organic compound that serves as a versatile reagent in various chemical reactions, particularly in palladium-catalyzed coupling processes. It is characterized by the presence of a benzyl group attached to a boronic acid moiety, with a pinacol ester protecting group. This structure allows it to participate in a wide range of synthetic transformations, making it a valuable building block in organic synthesis.

87100-28-5

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87100-28-5 Usage

Uses

Used in Pharmaceutical Industry:
Benzylboronic acid pinacol ester is used as a synthetic intermediate for the preparation of pharmaceutical compounds. Its ability to undergo palladium-catalyzed coupling reactions enables the formation of complex organic molecules, which are often found in drug candidates and active pharmaceutical ingredients.
Used in Organic Synthesis:
In the field of organic synthesis, benzylboronic acid pinacol ester is used as a reagent for the construction of various organic molecules. Its participation in palladium-catalyzed coupling reactions allows for the formation of carbon-carbon and carbon-heteroatom bonds, which are essential for the synthesis of a wide range of organic compounds.
Used in Pd (0)-mediated [11C] Carbonylation Reaction:
Benzylboronic acid pinacol ester finds application in Pd (0)-mediated [11C] carbonylation reactions, which are important for the synthesis of radiolabeled compounds used in positron emission tomography (PET) imaging. This application takes advantage of the reactivity of the boronic acid moiety in the presence of palladium catalysts, allowing for the incorporation of the radioactive carbon-11 isotope into the target molecule.

Check Digit Verification of cas no

The CAS Registry Mumber 87100-28-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,7,1,0 and 0 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 87100-28:
(7*8)+(6*7)+(5*1)+(4*0)+(3*0)+(2*2)+(1*8)=115
115 % 10 = 5
So 87100-28-5 is a valid CAS Registry Number.
InChI:InChI=1/C13H19BO2/c1-12(2)13(3,4)16-14(15-12)10-11-8-6-5-7-9-11/h5-9H,10H2,1-4H3

87100-28-5 Well-known Company Product Price

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  • TCI America

  • (B3448)  2-Benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane  >97.0%(GC)

  • 87100-28-5

  • 1g

  • 350.00CNY

  • Detail
  • TCI America

  • (B3448)  2-Benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane  >97.0%(GC)

  • 87100-28-5

  • 5g

  • 1,300.00CNY

  • Detail
  • Alfa Aesar

  • (H32523)  Benzylboronic acid pinacol ester, 96%   

  • 87100-28-5

  • 1g

  • 625.0CNY

  • Detail
  • Alfa Aesar

  • (H32523)  Benzylboronic acid pinacol ester, 96%   

  • 87100-28-5

  • 5g

  • 2007.0CNY

  • Detail
  • Alfa Aesar

  • (H32523)  Benzylboronic acid pinacol ester, 96%   

  • 87100-28-5

  • 25g

  • 7632.0CNY

  • Detail

87100-28-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Benzylboronic acid pinacol ester

1.2 Other means of identification

Product number -
Other names 4,4,5,5-tetramethyl-2-(phenylmethyl)-1,3,2-dioxaborolane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:87100-28-5 SDS

87100-28-5Relevant academic research and scientific papers

Cu-mediated: vs. Cu-free selective borylation of aryl alkyl sulfones

Hu, Jiefeng,Huang, Mingming,Marder, Todd B.,Radius, Udo,Tang, Man,Westcott, Stephen A.

supporting information, p. 395 - 398 (2022/01/19)

A Cu-catalysed borylation of aryl alkyl sulfones was developed for the high yield synthesis of versatile arylboronic esters using a readily prepared NHC-Cu catalyst. In addition, the selective cleavage of either alkyl(C)-sulfonyl or aryl(C)-sulfonyl bonds

Selective Benzylic CH-Borylations by Tandem Cobalt Catalysis

Bauer, Matthias,Ghosh, Pradip,Jacobi von Wangelin, Axel,Schoch, Roland

supporting information, (2021/11/27)

Metal-catalyzed C?H activations are environmentally and economically attractive synthetic strategies for the construction of functional molecules as they obviate the need for pre-functionalized substrates and minimize waste generation. Great challenges reside in the control of selectivities, the utilization of unbiased hydrocarbons, and the operation of atom-economical dehydrocoupling mechanisms. An especially mild borylation of benzylic CH bonds was developed with the ligand-free pre-catalyst Co[N(SiMe3)2]2 and the bench-stable and inexpensive borylation reagent B2pin2 that produces H2 as the only by-product. A full set of kinetic, spectroscopic, and preparative mechanistic studies are indicative of a tandem catalysis mechanism of CH-borylation and dehydrocoupling via molecular CoI catalysts.

Evaluation of the role of graphene-based Cu(i) catalysts in borylation reactions

Cid, M. B.,Díaz, Cristina,Franco, Mario,Lamsabhi, Al Mokhtar,Sainz, Raquel,Tortosa, Mariola

, p. 3501 - 3513 (2021/06/06)

Carbon-supported catalysts have been considered as macromolecular ligands which modulate the activity of the metallic catalytic center. Understanding the properties and the factors that control the interactions between the metal and support allows a fine tuning of the catalyzed processes. Although huge effort has been devoted to comprehending binding energies and charge transfer for single atom noble metals, the interaction of graphenic surfaces with cheap and versatile Cu(i) salts has been scarcely studied. A methodical experimental and theoretical analysis of different carbon-based Cu(i) materials in the context of the development of an efficient, general, scalable, and sustainable borylation reaction of aliphatic and aromatic halides has been performed. We have also examined the effect of microwave (MW) radiation in the preparation of these type of materials using sustainable graphite nanoplatelets (GNP) as a support. A detailed analysis of all the possible species in solution revealed that the catalysis is mainly due to an interesting synergetic Cu2O/graphene performance, which has been corroborated by an extensive theoretical study. We demonstrated through DFT calculations at a high level of theory that graphene enhances the reactivity of the metal in Cu2O against the halide derivative favoring a radical departure from the halogen. Moreover, this material is able to stabilize radical intermediates providing unexpected pathways not observed using homogeneous Cu(i) catalysed reactions. Finally, we proved that other common carbon-based supports like carbon black, graphene oxide and reduced graphene oxide provided poorer results in the borylation process.

Visible-light-driven graphene supported Cu/Pd alloy nanoparticle-catalyzed borylation of alkyl bromides and chlorides in air

Jiao, Zhi-Feng,Tian, Ya-Ming,Guo, Xiao-Ning,Radius, Udo,Braunschweig, Holger,Marder, Todd B.,Guo, Xiang-Yun

, p. 258 - 265 (2021/02/16)

A highly efficient photocatalytic protocol for borylation of alkyl bromides and chlorides with graphene supported Cu/Pd alloy nanoparticles as a heterogeneous catalyst is reported. This photocatalytic system operates with visible light in air, providing a wide range of primary and secondary alkyl halides with B2pin2 or B2neop2 in high yields at low temperatures, thereby demonstrating its broad utility and functional group tolerance. The high performance is attributed to a synergistic effect of localized surface plasmon resonance (LSPR) of Cu and charge transfer from Cu to Pd due to the alloy surface charge heterogeneity. Transfer of energetic electrons from Pd to electrophilic alkyl halides lead to the formation of the alkyl radicals, which quickly react with a nucleophilic adduct of a diboron compound with base adsorbed on the positively charged Cu sites to form the corresponding borylation product.

Photochemical Radical C–H Halogenation of Benzyl N-Methyliminodiacetyl (MIDA) Boronates: Synthesis of α-Functionalized Alkyl Boronates

Yang, Ling,Tan, Dong-Hang,Fan, Wen-Xin,Liu, Xu-Ge,Wu, Jia-Qiang,Huang, Zhi-Shu,Li, Qingjiang,Wang, Honggen

supporting information, p. 3454 - 3458 (2020/12/17)

α-Haloboronates are useful organic synthons that can be converted to a diverse array of α-substituted alkyl borons. Methods to α-haloboronates are limiting and often suffer from harsh reaction conditions. Reported herein is a photochemical radical C-H halogenation of benzyl N-methyliminodiacetyl (MIDA) boronates. Fluorination, chlorination, and bromination reactions were effective by using this protocol. Upon reaction with different nucleophiles, the C?Br bond in the brominated product could be readily transformed to a series of C?C, C?O, C?N, C?S, C?P, and C?I bonds, some of which are difficult to forge with α-halo sp2-B boronate esters. An activation effect of B(MIDA) moiety was found.

Structure-Based Optimization and Discovery of M3258, a Specific Inhibitor of the Immunoproteasome Subunit LMP7 (β5i)

Klein, Markus,Busch, Michael,Friese-Hamim, Manja,Crosignani, Stefano,Fuchss, Thomas,Musil, Djordje,Rohdich, Felix,Sanderson, Michael P.,Seenisamy, Jeyaprakashnarayanan,Walter-Bausch, Gina,Zanelli, Ugo,Hewitt, Philip,Esdar, Christina,Schadt, Oliver

, p. 10230 - 10245 (2021/07/26)

Proteasomes are broadly expressed key components of the ubiquitin-dependent protein degradation pathway containing catalytically active subunits (β1, β2, and β5). LMP7 (β5i) is a subunit of the immunoproteasome, an inducible isoform that is predominantly expressed in hematopoietic cells. Clinically effective pan-proteasome inhibitors for the treatment of multiple myeloma (MM) nonselectively target LMP7 and other subunits of the constitutive proteasome and immunoproteasome with comparable potency, which can limit the therapeutic applicability of these drugs. Here, we describe the discovery and structure-based hit optimization of novel amido boronic acids, which selectively inhibit LMP7 while sparing all other subunits. The exploitation of structural differences between the proteasome subunits culminated in the identification of the highly potent, exquisitely selective, and orally available LMP7 inhibitor 50 (M3258). Based on the strong antitumor activity observed with M3258 in MM models and a favorable preclinical data package, a phase I clinical trial was initiated in relapsed/refractory MM patients.

(o-Phenylenediamino)borylstannanes: Efficient Reagents for Borylation of Various Alkyl Radical Precursors

Suzuki, Kensuke,Nishimoto, Yoshihiro,Yasuda, Makoto

supporting information, p. 3968 - 3973 (2020/12/30)

(o-Phenylenediamino)borylstannanes were newly synthesized to achieve radical boryl substitutions of a variety of alkyl radical precursors. Dehalogenative, deaminative, decharcogenative, and decarboxylative borylations proceeded in the presence of a radica

Arene borylation through C–H activation using Cu3(BTC)2 as heterogeneous catalyst

Dhakshinamoorthy, Amarajothi,García, Cristina Vallés,Concepcion, Patricia,Garcia, Hermenegildo

, p. 212 - 217 (2020/07/06)

C–H borylation by diborane is an important process to access organoboron compounds. Noble metals, including Ir and Rh-based complexes either in the form of homogeneous or heterogeneous catalysts, have been reported to promote arene C–H borylation. Recently, metal organic frameworks (MOFs) having Ir and Co as active sites have been used as catalysts, but they require co-catalysts. In the present study, commercially available Cu3(BTC)2 (BTC: 1,3,5-benzenetricarboxylate) MOF is reported as an effective catalyst to promote borylation of arenes through C–H activation employing bis(pinacolato)diboron (1) as reagent leading to benzylic and aromatic borylation products. Interestingly, other related MOFs like MIL-101(Cr) and Al(OH)(BDC) (BDC: 1,4-benzenedicarboxylate) do not exhibit catalytic activity under identical conditions. Mechanistic studies using in-situ IR spectroscopy reveal that Cu ions play a crucial role in activating the arene and B–B bond in 1.

Photoinduced NaI-Promoted Radical Borylation of Alkyl Halides and Pseudohalides

Wang, Chenglan,Zhou, Lu,Yang, Kai,Zhang, Feng,Song, Qiuling

supporting information, p. 1825 - 1830 (2021/05/28)

A method for photoinduced NaI-promoted radical borylation of aliphatic halides and pseudohalides with bis(catecholato)diboron (B2cat2) as the boron source is introduced. The borylation reaction is operationally simple and shows high

Practical Synthesis of Allyl, Allenyl, and Benzyl Boronates through SN1′-Type Borylation under Heterogeneous Gold Catalysis

Miura, Hiroki,Hachiya, Yuka,Nishio, Hidenori,Fukuta, Yohei,Toyomasu, Tomoya,Kobayashi, Kosa,Masaki, Yosuke,Shishido, Tetsuya

, p. 758 - 766 (2021/02/03)

Efficient borylation of sp3 C-O bonds by supported Au catalysts is described. Au nanoparticles supported on TiO2 showed high activity under mild conditions employing low catalyst loading conditions without the aid of any additives, such as phosphine and bases. A variety of allyl, propargyl, and benzyl substrates participated in the heterogeneously catalyzed reactions to furnish the corresponding allyl, allenyl, and benzyl boronates in high yields. Besides, Au/TiO2 was also effective for the direct borylation of allylic and benzylic alcohols. A mechanistic investigation based on a Hammett study and control experiments revealed that sp3 C-O bond borylation over supported Au catalysts proceeded through SN1′-type mechanism involving the formation of a carbocationic intermediate. The high activity, reusability, and environmental compatibility of the supported Au catalysts as well as the scalability of the reaction system enable the practical synthesis of valuable organoboron compounds.

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