1186026-67-4

Basic information

• Product Name: 4-TRIMETHYLSILYLBENZENEBORONIC ACID PINACOL ESTER
• Synonyms: 4-TRIMETHYLSILYLBENZENEBORONIC ACID PINACOL ESTER;4-TriMethylsilylphenylboronic acid pinacol ester;Trimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)trimethylsilylbenzene
• CAS NO: 1186026-67-4
• Molecular Formula: C₁₅H₂₅BO₂Si
• Molecular Weight: 294.26958
• Mol File: 1186026-67-4.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 335.4 °C at 760 mmHg
• Flash Point: 156.7 °C
• Appearance: /
• Density: 0.95 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-TRIMETHYLSILYLBENZENEBORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TRIMETHYLSILYLBENZENEBORONIC ACID PINACOL ESTER(1186026-67-4)
• EPA Substance Registry System: 4-TRIMETHYLSILYLBENZENEBORONIC ACID PINACOL ESTER(1186026-67-4)

Safety Data

• Hazardous Substances Data: 1186026-67-4(Hazardous Substances Data)

Usage

General Description

4-Trimethylsilylbenzeneboronic acid pinacol ester is a chemical compound commonly used in organic synthesis as a reagent for the introduction of the boronic ester functional group. It is a derivative of benzeneboronic acid and contains a trimethylsilyl functional group, which can be easily removed under mild conditions to reveal the boronic acid. The pinacol ester moiety serves as a protecting group, allowing for the selective manipulation of the boronic acid group. 4-TRIMETHYLSILYLBENZENEBORONIC ACID PINACOL ESTER is highly useful in the synthesis of pharmaceuticals, agrochemicals, and materials science, and is a valuable tool for the construction of carbon-carbon and carbon-heteroatom bonds in organic molecules.

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 768-32-1 trimethylphenylsilane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 75-77-4 chloro-trimethyl-silane 
• 106-37-6 1.4-dibromobenzene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 16087-24-4 N,N-dimethyl-4-(trimethylsilyl)aniline 
• 195062-61-4 4-chlorophenylboronic acid pinacol ester 
• 17865-11-1 (4-(trimethylsilyl)phenyl)boronic acid 
• 17882-12-1 4-trimethylsilylbenzenethiol 
• 22515-25-9 [4-(methylsulfanyl)phenyl]trimethylsilane 
• 6999-03-7 1-bromo-4-(trimethylsilyl)benzene 

Downstream Products

• 1334531-92-8 methyl 2-(4-chlorophenyl)-2-(4-(trimethylsilyl)phenyl)-3-phenylpropanoate 
• 17889-23-5 4-(trimethylsilyl)aniline 
• 1443645-30-4 9,9-dihexyl-7-(4-(trimethylsilyl)phenyl)-9H-fluorene-2-carbaldehyde 
• 1395931-80-2 2-(4-(trimethylsilyl)phenyl)-4H-chromen-4-one 
• 871012-88-3 2-(4-iodophenyl)pyridine 
• 78313-73-2 3-(p-iodophenyl)pyridine 
• 312-75-4 trimethyl(4-trifluoromethylphenyl)silane 
• 455-17-4 (p-fluorophenyl)trimethylsilane 

Relevant articles and documents

A synthetic approach to dimetalated arenes using flow microreactors and the switchable application to chemoselective cross-coupling reactions

In spite of their potential utility, the chemistry of dimetalated arenes is still in its infancy because they are extremely difficult to synthesize. We report a novel method of synthesizing arenes bearing a boryl group and a metallic substituent, such as boryl, silyl, stannyl, or zincyl groups, in an integrated flow microreactor based on the generation and reactions of aryllithiums bearing a trialkyl borate moiety. The bimetallic arenes showed a remarkable chemoselectivity in palladium-catalyzed cross-coupling reactions. The selectivity was switched by the selection of the metal species that constitutes the dimetalated arenes as well as appropriate catalysts.

Remote steric control for undirected meta-selective C-H activation of arenes

Regioselective functionalization of arenes remains a challenging problem in organic synthesis. Steric interactions are often used to block sites adjacent to a given substituent, but they do not distinguish the remaining remote sites. We report a strategy

Azimuthal Dipolar Rotor Arrays on Surfaces

A set of dipolar molecular rotor compounds was designed, synthesized and adsorbed as self-assembled 2D arrays on Ag(111) surfaces. The title molecules are constructed from three building blocks: (a) 4,8,12-trioxatriangulene (TOTA) platforms that are known to physisorb on metal surfaces such as Au(111) and Ag(111), (b) phenyl groups attached to the central carbon atom that function as pivot joints to reduce the barrier to rotation, (c) pyridine and pyridazine units as small dipolar units on top. Theoretical calculations and scanning tunneling microscopy (STM) investigations hint at the fact that the dipoles of neighboring rotors interact through space through pairs of energetically favorable head-to-tail arrangements.

Sodium silylsilanolate enables nickel-catalysed silylation of aryl chlorides

Structurally diverse aryl chlorides were silylated with sodium silylsilanolate reagents in the presence of a Ni(cod)2catalyst complexed with a phosphine ligand; PMe2Ph for electron-rich substrates, and PCy2Ph for electron-deficient ones. The mild reaction conditions allowed the silylation of various aryl chlorides including functionalised drug molecules.