154230-29-2

Basic information

• Product Name: TRANS-2-(4-CHLOROPHENYL)VINYLBORONIC ACID
• Synonyms: TRANS-2-(4-CHLOROPHENYL)VINYLBORONIC ACID;RARECHEM AL BA 0169;TRANS-2-(4-CHLOROPHENYL)VINYLBORONIC ACI;TRANS-2-(4-CHLORPHENYL)VINYLBORONIC ACID;trans-2-(4-Chlorophenyl)ethenylboronic acid;Boronic acid, [(1E)-2-(4-chlorophenyl)ethenyl]-;(4-Chlorostyryl)boronic acid
• CAS NO: 154230-29-2
• Molecular Formula: C₈H₈BClO₂
• Molecular Weight: 182.41
• Product Categories: Alkenyl;Boronic Acids;Boronic Acids and Derivatives;Alkenyl Boronic Acids;Boronic Acids;Boronic Acids and Derivatives;Chemical Synthesis;Organometallic Reagents
• Mol File: 154230-29-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 165 °C (dec.)(lit.)
• Boiling Point: 356.7°Cat760mmHg
• Flash Point: 169.6°C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.277g/cm³
• Vapor Pressure: 1.04E-05mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.55±0.43(Predicted)
• CAS DataBase Reference: TRANS-2-(4-CHLOROPHENYL)VINYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-2-(4-CHLOROPHENYL)VINYLBORONIC ACID(154230-29-2)
• EPA Substance Registry System: TRANS-2-(4-CHLOROPHENYL)VINYLBORONIC ACID(154230-29-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 154230-29-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 154230-29-2 differently. You can refer to the following data:
1. Reactant involved in:? ;Synthesis of biarylketones and phthalides1? ;Trifluoromethylation2? ;Asymmetrical Michael addition for preparation of chromanes3? ;Cobalt-catalyzed coupling to vinyl nitrogen containing heteroaromatic compounds4? ;1,2 and 1,4-Addition reactions with o-hydroxycinnamaldehydes5? ;Petasis reactions6
2. Reactant involved in:Synthesis of biarylketones and phthalidesTrifluoromethylationAsymmetrical Michael addition for preparation of chromanesCobalt-catalyzed coupling to vinyl nitrogen containing heteroaromatic compounds1,2 and 1,4-Addition reactions with o-hydroxycinnamaldehydesPetasis reactions

InChI:InChI=1/C8H8BClO2/c10-8-3-1-7(2-4-8)5-6-9(11)12/h1-6,11-12H/b6-5+

Upstream product

• 873-73-4 4-n-chlorophenylacetylene 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 223919-54-8 2-[(E)-2-(4-chlorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 223919-54-8 2-[(E)-2-(4-chlorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 166823-93-4 (2E)-1,3-bis(4-chlorophenyl)prop-2-en-1-ol 
• 1007197-63-8 (E)-tert-butyl 4-(benzyloxy)-5-(tert-butoxycarbonylamino)-8-methyl-7-oxo-7,8-dihydropyrimido[4,5-d]pyrimidin-2-yl(4-(4-chlorostyryl)phenyl)carbamate 
• 1007197-62-7 (E)-tert-butyl 4-(benzyloxy)-5-(di(tert-butoxycarbonyl)amino)-8-methyl-7-oxo-7,8-dihydropyrimido[4,5-d]pyrimidin-2-yl(4-(4-chlorostyryl)phenyl)carbamate 
• 1107658-36-5 1-{3-[(E)-2-(4-chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazole-4-carboxylic acid methyl ester 
• 1054567-88-2 (E)-2-(4-chlorostyryl)aniline 
• 1233193-92-4 C₁₈H₁₂BrCl 
• 168006-99-3 (E)-1-chloro-4-(2-iodovinyl)benzene 
• 1241889-99-5 (E)-3-(5-(4-chlorostyryl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-N,N-dimethylpropan-1-amine 
• 1268398-47-5 4-benzyl-5R-phenyl-3R-(E-2-(4-chlorophenyl)ethenyl)-morpholin-2-one 
• 1370009-80-5 (R,E)-4-(4-chlorophenyl)-2-((R)-1,1-dimethylethylsulfinamido)but-3-enoic acid 
• 1393683-08-3 1-chloro-4-(2-cyclohexylideneethyl)benzene 
• 1393683-18-5 1-chloro-4-(2-(4-phenylcyclohexylidene)ethyl)benzene 
• 1529778-66-2 (E)-2-[3-(4-chlorobenzoyl)-5-(2-(4-chlorophenyl)ethen-1-yl)-4-(2,2-dimethyl-propyl)thiophen-2-yl]isoindoline-1,3-dione 

Relevant articles and documents

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.

Anomalies in the stereoselectivity of the petasis reaction using styrenyl boronic acids

The Petasis three-component coupling reaction of N-benzylphenylglycinol, glyoxylic acid, and styrenylboronic acids allows for the efficient synthesis of functionalized homoarylalanine derivatives. The reactions were shown to proceed in high yield but low selectivity, regardless of the nature of the substituent on the styrenylboronic acid component. Anomalies in the stereoselectivity of these reactions compared with previously reported results have been traced to the source of the organoboronic acid. Asymmetric dihydroxylation of the unsaturated amino acid derivatives enables a highly efficient route to dihydroxyhomoarylalanine derivatives. CSIRO 2011.