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

• 100-42-5 styrene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 24182-83-0 (E)-styryl(p-tolyl)sulfane 
• 100-52-7 benzaldehyde 
• 100-41-4 ethylbenzene 
• 10521-96-7 styryl acetate 
• 73183-34-3 bis(pinacol)diborane 
• 177698-19-0 Beta-pinene 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 622-24-2 2-phenylethyl chloride 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 103-63-9 1-phenyl-2-bromoethane 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 

Downstream Products

• 60-12-8 2-phenylethanol 
• 935662-30-9 (R)-2-(1,4-diphenyl-2-butyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 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

Manganese(III)-Promoted Double Carbonylation of Anilines Toward α-Ketoamides Synthesis

Employing anilines as nucleophiles in double carbonylation is a longstanding challenge. In this communication, a Mn(III)-promoted double carbonylation of alkylborates or Hantzsch esters with anilines toward the synthesis of α-ketoamides has been developed. By using easily available potassium alkyltrifluoroborates or Hantzsch esters as the starting material, and cheap and non-toxic Mn(OAc)3 ? 2H2O as the promotor, a broad range of alkyl α-ketoamide derivatives were synthesized in moderate to good yields with excellent selectivity. (Figure presented.).

Neosilyllithium-Catalyzed Hydroboration of Alkynes and Alkenes in the Presence of Pinacolborane (HBpin)

We report here a novel protocol for the hydroboration of alkynes and alkenes, which in the presence of neosilyllithium (LiCH2SiMe3) (5 mol %) and pinacolborane efficiently results in the formation of corresponding alkenyl and alkyl b

Electrochemical Borylation of Alkyl Halides: Fast, Scalable Access to Alkyl Boronic Esters

Herein, a fast, scalable, and transition-metal-free borylation of alkyl halides (X = I, Br, Cl) enabled by electroreduction is reported. This process provides an efficient and practical access to primary, secondary, and tertiary boronic esters at a high current. More than 70 examples, including the late-stage borylation of natural products and drug derivatives, are furnished at room temperature, thereby demonstrating the broad utility and functional-group tolerance of this protocol. Mechanistic studies disclosed that B2cat2 serves as both a reagent and a cathodic mediator, enabling electroreduction of difficult-to-reduce alkyl bromides or chlorides at a low potential.