72316-17-7

Basic information

• Product Name: TRANS-2-(4-METHYLPHENYL)VINYLBORONIC AC&
• Synonyms: 1-(4-Methylphenyl)-vinyl-2-boronic acid;(4-Methylstyryl)boronic acid;(E)-(4-Methylstyryl)boronic acid;trans-2-(4-Methylphenyl)vinylboronic acid 97%;TRANS-2-(4-METHYLPHENYL)VINYLBORONIC;TRANS-2-(4-METHYLPHENYL)VINYLBORONIC AC&
• CAS NO: 72316-17-7
• Molecular Formula: C₉H₁₁BO₂
• Molecular Weight: 161.995
• Product Categories: Boronic Acids and Derivatives;Alkenyl;Boronic Acids
• Mol File: 72316-17-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 169-175 °C(lit.)
• Boiling Point: 330.9°C at 760 mmHg
• Flash Point: 154°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 6.43E-05mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: TRANS-2-(4-METHYLPHENYL)VINYLBORONIC AC&(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-2-(4-METHYLPHENYL)VINYLBORONIC AC&(72316-17-7)
• EPA Substance Registry System: TRANS-2-(4-METHYLPHENYL)VINYLBORONIC AC&(72316-17-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 72316-17-7(Hazardous Substances Data)

Usage

General Description

Contains varying amount of anhydride

InChI:InChI=1/C9H11BO2/c1-8-2-4-9(5-3-8)6-7-10(11)12/h2-7,11-12H,1H3/b7-6+

Upstream product

• 766-97-2 4-n-methylphenylacetylene 
• 174153-82-3 CH₃C₆H₄CHCHB(O₂C₆H₄) 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 149777-84-4 4,4,5,5-tetramethyl-2-[(E)-2-p-tolylethenyl]-1,3,2-dioxaborolane 
• 121-43-7 Trimethyl borate 

Downstream Products

• 72033-82-0 trans,trans-1,4-bis(4-methylphenyl)-1,3-butadiene 
• 876955-10-1 5-(p-methyl-styryl)-4,6-diaminopyrimidine 
• 149777-84-4 4,4,5,5-tetramethyl-2-[(E)-2-p-tolylethenyl]-1,3,2-dioxaborolane 
• 880263-74-1 (E)-ethyl 2-(4-methylstyryl)-1H-indole-1-carboxylate 
• 24325-70-0 (E)-4-methyl-4'-nitrostilbene 

Relevant articles and documents

Rate dependence on inductive and resonance effects for the organocatalyzed enantioselective conjugate addition of alkenyl and alkynyl boronic acids to β-indolyl enones and β-pyrrolyl enones

Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the enone β-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Thus, reaction rates are increased by the closer proximity of inductive electron-withdrawing elements, but if resonance effects are involved, then increased rates are observed with electron-donating ability. Evidence for these trends in isomeric substrates is presented, and the application of these insights has allowed for reaction conditions that provide improved reactivity with previously problematic substrates.

ASYMMETRIC ADDITION REACTIONS

Processes of forming Csp2-Csp3 bonds at the allylic carbon of a cyclic allylic compound starting material are disclosed, in which a racemic mixture of a cyclic allylic compound having a leaving group attached to the allylic carbon is reacted with a compound having a nucleophilic carbon atom in the presence of a Rh(l), Pd(ll) or Cu(l) pre-catalyst and a chiral ligand. The reaction products containing the newly-formed Csp2-Csp3 bond are generated in high stereoisomeric excess, and may therefore serve as important organic building blocks in the preparation of new agrochemicals and pharmaceuticals.

Rhodium(III)-catalyzed cross-coupling of alkenylboronic acids and N -pivaloyloxylamides

Rh(III)-catalyzed umpolung amidation of alkenylboronic acids for the synthesis of enamides is reported. This reaction proceeds readily at room temperature and displays an extremely wide spectrum of functional group tolerance. With cooperation of hydrobora