4363-35-3

Basic information

• Product Name: 2-PHENYLVINYLBORONIC ACID
• Synonyms: 2-PHENYLVINYLBORONIC ACID;(E)-2-PHENYLETHENYL-1-BORONIC ACID
• CAS NO: 4363-35-3
• Molecular Formula: C₈H₉BO₂
• Molecular Weight: 147.96686
• Mol File: 4363-35-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 138-141 °C
• Boiling Point: 315.9°Cat760mmHg
• Flash Point: 144.9°C
• Appearance: /
• Density: 1.13g/cm³
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 9.38±0.43(Predicted)
• CAS DataBase Reference: 2-PHENYLVINYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYLVINYLBORONIC ACID(4363-35-3)
• EPA Substance Registry System: 2-PHENYLVINYLBORONIC ACID(4363-35-3)

Safety Data

• Hazardous Substances Data: 4363-35-3(Hazardous Substances Data)

Usage

General Description

2-Phenylvinylboronic acid is a chemical compound with the formula C8H9BO2. It is a boronic acid derivative that is commonly used in organic synthesis, particularly in the formation of carbon-carbon bonds through the Suzuki-Miyaura coupling reaction. 2-PHENYLVINYLBORONIC ACID serves as a reactant in the preparation of various functionalized organic molecules, such as pharmaceuticals, agrochemicals, and materials. 2-Phenylvinylboronic acid is known for its ability to act as a versatile building block in the synthesis of complex organic compounds due to its reactivity and stability under a wide range of reaction conditions. It is an important tool in the arsenal of synthetic organic chemists.

Upstream product

• 7732-18-5 water 
• 536-74-3 phenylacetylene 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 78782-27-1 4,4,5,5-tetramethyl-2-styryl-[1,3,2]dioxaborolane 
• 13195-76-1 triisobutyl borate 
• 103-64-0 bromostyrene 

Downstream Products

• 943344-29-4 (2E)-1-(2-methyl-3,4-dihydro-2H-pyran-6-yl)-3-phenylprop-2-en-1-one 
• 395102-14-4 3-((1E)-2-Phenylvinyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile 
• 909010-91-9 7-hydroxy-2-styryl-thieno[3,2-c]pyridine-6-carboxylic acid ethyl ester 
• 58207-08-2 (E)-2-amino-4-phenyl-3-butenoic acid 
• 84680-54-6 enalaprilic acid 
• 1109183-48-3 ((1E,3Z)-5,5-difluoro-3-(methoxymethyl)-5-(phenylsulfonyl)penta-1,3-dienyl)benzene 
• 1109183-44-9 (((1E,3E)-3-2,2-difluoro-2-(phenylsulfonyl)ethylidene)hept-1-enyl)benzene 

Relevant articles and documents

Cu-catalyzed [2 + 2 + 1] cascade annulation of vinyl iodonium salts with elemental sulfur/selenium for the modular synthesis of thiophenes and selenophenes

A [2 + 2 + 1] annulation protocol has been established for the modular synthesis of 2,4-disubstituted thiophenes/selenophenes, with excellent regioselectivity. The reactions have been catalyzed by copper salt with elemental sulfur and selenium serving as

Transition-Metal-Free C(sp2)–C(sp2) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters

A transition-metal-free C(sp2)?C(sp2) bond formation reaction by the cross-coupling of diazo quinones with catechol boronic esters was developed. With this protocol, a variety of biaryls and alkenyl phenols were obtained in good to high yields under mild conditions. The reaction tolerates various functionalities and is applicable to the derivatization of pharmaceuticals and natural products. The synthetic utility of the method was demonstrated by the short synthesis of multi-substituted triphenylenes and three bioactive natural products, honokiol, moracin M, and stemofuran A. Mechanistic studies and density functional theory (DFT) calculations revealed that the reaction involves attack of the boronic ester by a singlet quinone carbene followed by a 1,2-rearrangement through a stepwise mechanism.

Synthesis of α-Borylated Ketones by Regioselective Wacker Oxidation of Alkenylboronates

As part of a program aimed at metal-catalyzed oxidative transformations of molecules with carbon-metalloid bonds, the synthesis of α-borylated ketones is reported via regioselective TBHP-mediated Wacker-type oxidation of N-methyliminodiacetic acid (MIDA)-protected alkenylboronates. The observed regioselectivity correlates with the hemilabile nature of the B-N dative bond in the MIDA boronate functional group, which allows boron to guide selectivity through a neighboring group effect.