165904-22-3

Basic information

• Product Name: 2-PHENYLETHYL-1-BORONIC ACID PINACOL ESTER
• Synonyms: 2-PHENYLETHYL-1-BORONIC ACID PINACOL ESTER;2-Phenylethylboronic acid, pinacol ester;4,4,5,5-tetraMethyl-2-(2-phenylethyl)-1,3,2-dioxaborolane;4,4,5,5-TetraMethyl-2-phenethyl-1,3,2-dioxaborolane;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(2-phenylethyl)-
• CAS NO: 165904-22-3
• Molecular Formula: C₁₄H₂₁BO₂
• Molecular Weight: 232.13
• EINECS: -0
• Mol File: 165904-22-3.mol
• Article Data: 182

Chemical Properties

• Melting Point: 31-33℃
• Boiling Point: 70-80℃
• Flash Point: 129.4°C
• Appearance: /
• Density: 0.97g/cm³
• Vapor Pressure: 0.00363mmHg at 25°C
• Refractive Index: 1.4860
• BRN: 8258927
• CAS DataBase Reference: 2-PHENYLETHYL-1-BORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYLETHYL-1-BORONIC ACID PINACOL ESTER(165904-22-3)
• EPA Substance Registry System: 2-PHENYLETHYL-1-BORONIC ACID PINACOL ESTER(165904-22-3)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 165904-22-3(Hazardous Substances Data)

Usage

General Description

2-PHENYLETHYL-1-BORONIC ACID PINACOL ESTER is a boronic acid derivative that is used in organic synthesis as a reagent for the Suzuki-Miyaura cross-coupling reaction, which is a widely used method for the formation of carbon-carbon bonds. It is often used as a building block in the synthesis of various biologically active compounds, pharmaceuticals, and agrochemicals. The pinacol ester group provides stability and can be easily removed under mild conditions, making it a versatile and valuable tool in organic chemistry. 2-PHENYLETHYL-1-BORONIC ACID PINACOL ESTER is also known for its mild and selective properties, making it an attractive choice for the modification of complex molecules.

InChI:InChI=1/C14H21BO2/c1-13(2)14(3,4)17-15(16-13)11-10-12-8-6-5-7-9-12/h5-9H,10-11H2,1-4H3

Upstream product

• 100-41-4 ethylbenzene 
• 73183-34-3 bis(pinacol)diborane 
• 100-42-5 styrene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 100-52-7 benzaldehyde 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 592-41-6 1-hexene 
• 17376-04-4 2-phenethyl iodide 
• 108-86-1 bromobenzene 
• 159087-45-3 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane 
• 622-24-2 2-phenylethyl chloride 
• 2114-39-8 (2-bromopropyl)-benzene 
• 103-63-9 1-phenyl-2-bromoethane 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 

Downstream Products

• 935662-30-9 (R)-2-(1,4-diphenyl-2-butyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 60-12-8 2-phenylethanol 
• 2344-70-9 (+)-(S)-4-phenylbutan-2-ol 
• 2344-70-9 (R)-4-phenyl-2-butanol 
• 105836-17-7 (R)-1-phenyl-3-pentanol 
• 71747-37-0 (S)-1-phenylpentan-3-ol 
• 17486-86-1 1,5-diphenylpentan-3-ol 
• 935662-21-8 (S)-2-(1,4-diphenyl-2-butyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1142-21-8 (Z)-1,4-diphenylbut-2-ene 
• 1142-22-9 (E)-1,4-diphenylbut-2-ene 
• 622-24-2 2-phenylethyl chloride 
• 1361022-83-4 2-fluoro-4-phenethylbiphenyl 
• 1373874-51-1 (R,E)-3-methyl-1-phenylhex-4-en-3-ol 
• 182965-24-8 (Z)-4-hydroxypent-2-en-2-yl diisopropylcarbamate 

Relevant articles and documents

1,2-Boron Shifts of β-Boryl Radicals Generated from Bis-boronic Esters Using Photoredox Catalysis

1,2-Bis-boronic esters are versatile intermediates that enable the rapid elaboration of simple alkene precursors. Previous reports on their selective mono-functionalization have targeted the most accessible position, retaining the more hindered secondary boronic ester. In contrast, we have found that photoredox-catalyzed mono-deboronation generates primary β-boryl radicals that undergo rapid 1,2-boron shift to form thermodynamically favored secondary radicals, allowing for selective transformation of the more hindered boronic ester. The pivotal 1,2-boron shift, which has been demonstrated to be stereoretentive, enables access to a wide range of functionalized boronic esters and has been applied to highly diastereoselective fragmentation and transannular cyclization reactions. Furthermore, its generality has been shown in a radical cascade reaction with an allylboronic ester.

Palladium-catalyzed benzylic C-H borylation of alkylbenzenes with bis(pinacolato)diboron or pinacolborane

Borylation at the benzylic C-H bond of alkylbenzenes with bis(pinacolato)diboron [(Me4C2O2)B-B(O2C2Me 4)] or pinacolborane [(Me4C2O2)B-H] was carried out at

Rh(I)-catalyzed borylation of primary alkyl chlorides

Rhodium-catalyzed cross-coupling reactions of unactivated primary alkyl chlorides with diboron reagents have been developed as practical methods for the synthesis of alkylboronic esters. These reactions expand the concept and utility of Rh(I)-catalyzed cr

Fundamental organometallic chemistry under bimetallic influence: Driving β-hydride elimination and diverting migratory insertion at Cu and Ni

Bimetallic effects on stoichiometric β-hydride elimination and migratory insertion reactions were examined. Bimetallic reaction conditions drove β-hydride elimination at Cu, while bimetallic C-B elimination occurred in the absence of β-hydrogens. The inhe

Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes

The enantioselective hydroboration of vinylarenes catalyzed by a chiral, nonracemic nickel catalyst is presented as a facile method for generating chiral benzylic boronate esters. Various vinylarenes react with bis(pinacolato)diboron (B2pin2) in the presence of MeOH as a hydride source to form chiral boronate esters in up to 92% yield with up to 94% ee. The use of anhydrous Me4NF to activate B2pin2 is crucial for ensuring fast transmetalation to achieve high enantioselectivities.

Borohydrogenation reaction method of halide calcium catalyzed olefins

The present invention discloses a method of borohydrogenation of olefins catalyzed by calcium halide, comprising, under anhydrous and anaerobic conditions, calcium halide added to the mixture of olefins and pinacol borane, stirred at 90 to 110 ° C for 6 t

Rhodium-Catalyzed Regiodivergent Synthesis of Alkylboronates via Deoxygenative Hydroboration of Aryl Ketones: Mechanism and Origin of Selectivities

Here, we report an efficient rhodium-catalyzed deoxygenative borylation of ketones to synthesize alkylboronates, in which the regioselectivity can be switched by the choice of the ligand. The linear alkylboronates were obtained exclusively in the presence of P(nBu)3, and PPh2Me favored the formation of branched alkylboronates. The protocol also allows access to 1,1,2-triboronates from the readily available ketones. Mechanistic studies suggest that this Rh-catalyzed deoxygenative borylation of ketones goes through an alkene intermediate, which undergoes regiodivergent hydroboration to afford linear and branched alkylboronates. The different steric effects of PPh2Me and P(nBu)3 were found to be responsible for product selectivity by density functional theory calculations. The alkene intermediate can alternatively undergo sequential dehydrogenative borylation and hydroboration to deliver the triboronates.