87100-28-5

Basic information

• Product Name: BENZYLBORONIC ACID PINACOL ESTER
• Synonyms: 2-BENZYL-4,4,5,5-TETRAMETHYL-(1,3,2)DIOXABOROLANE;Benzylboronic acid pinacol est;4,4,5,5-Tetramethyl-2-(phenylmethyl)-1,3,2-dioxaborolane;Benzylboronic acid pinacol ester 96%;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen benzylboronate
• CAS NO: 87100-28-5
• Molecular Formula: C₁₃H₁₉BO₂
• Molecular Weight: 218.1
• Product Categories: Heterocyclic Compounds;Aryl;Boronic ester;Organoborons;Alkyl Boronate Esters;Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;Organometallic Reagents
• Mol File: 87100-28-5.mol
• Article Data: 77

Chemical Properties

• Boiling Point: 65 °C0.15 mm Hg
• Flash Point: >230 °F
• Appearance: /
• Density: 0.980 g/mL at 25 °C
• Vapor Pressure: 0.0119mmHg at 25°C
• Refractive Index: n20/D 1.490
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: BENZYLBORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYLBORONIC ACID PINACOL ESTER(87100-28-5)
• EPA Substance Registry System: BENZYLBORONIC ACID PINACOL ESTER(87100-28-5)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 87100-28-5(Hazardous Substances Data)

Usage

Description

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.

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.

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

Upstream product

• 960-16-7 tributylphenylstannane 
• 166330-03-6 pinacol (bromomethyl)boronate 
• 100-39-0 benzyl bromide 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 745783-97-5 triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 108-88-3 toluene 
• 73183-34-3 bis(pinacol)diborane 
• 32897-80-6 2-benzyl-5-methoxy-1-methyl-indole 
• 162213-35-6 C₁₃H₂₁BO₂ 
• 1589-82-8 phenylmagnesium bromide 
• 100-44-7 benzyl chloride 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 4463-42-7 benzyl boronic acid 
• 3112-88-7 Benzyl phenyl sulfone 

Downstream Products

• 1415043-70-7 Ethyl [3-(2-benzylbenzyl)-2-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-1-yl]acetate 
• 57693-15-9 2-benzyl-3-chloropyrazine 
• 6052-66-0 1-phenyl-3-buten-2-ol 
• 1457967-20-2 N^4,6-dibenzyl-3-nitro-N²-(2,4,4-trimethylpentan-2-yl)pyridine-2,4-diamine 
• 1449680-47-0 1-benzyl-2-butylfuro[2,3-c]quinoline 
• 100-41-4 ethylbenzene 

Relevant articles and documents

Selective Benzylic CH-Borylations by Tandem Cobalt Catalysis

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.

The functionalization of benzene by boranes using trispyrazolylborate complexes

The catalytic C[sbnd]H activation and borylation of arenes by trispyrazolylborate complexes is reported. Trispyrazolylborate rhodium and iridium complexes have been previously shown to activate a variety of C[sbnd]H bonds. Here, we show the catalytic borylation of arenes by the trispyrazolylborate ethylene complexes Tp'Rh(C2H4)2, and Tp'Ir(C2H4)2.

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

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.