1241903-34-3

Basic information

• Product Name: (Z)-2-(2-bromo-2-phenylvinyl)4,4,5,5-tetramethyl1,3,2-dioxaborolane
• Synonyms: (Z)-2-(2-bromo-2-phenylvinyl)4,4,5,5-tetramethyl1,3,2-dioxaborolane
• CAS NO: 1241903-34-3
• Molecular Weight: 309.011
• Mol File: 1241903-34-3.mol

Chemical Properties

• CAS DataBase Reference: (Z)-2-(2-bromo-2-phenylvinyl)4,4,5,5-tetramethyl1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-(2-bromo-2-phenylvinyl)4,4,5,5-tetramethyl1,3,2-dioxaborolane(1241903-34-3)
• EPA Substance Registry System: (Z)-2-(2-bromo-2-phenylvinyl)4,4,5,5-tetramethyl1,3,2-dioxaborolane(1241903-34-3)

Safety Data

• Hazardous Substances Data: 1241903-34-3(Hazardous Substances Data)

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 536-74-3 phenylacetylene 
• 51246-14-1 Br₂BCHCBr(C₆H₅) 

Downstream Products

• 1241903-42-3 (E)-2-phenyl-1,3-butadienyl(pinacol)borane 
• 1241903-38-7 (E)-2-phenyl-1-octenyl(pinacol)borane 
• 1241903-46-7 (1E,3E)-4-methyl-2-phenyl-1,3-decadienyl(pinacol)borane 
• 1241903-44-5 (Z)-2-(4-chlorophenyl)-2-phenylethenyl(pinacol)borane 
• 1241903-43-4 (Z)-2-(4-methoxyphenyl)-2-phenylethenyl(pinacol)borane 
• 1241903-41-2 (E)-2-(2-cyclohexyl-2-phenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 86474-75-1 2-(β-methylstyryl)thiophene 
• 1241903-50-3 (E)-(1-cyclohexyl-2-iodoethenyl)benzene 

Relevant articles and documents

Scope and mechanism in palladium-catalyzed isomerizations of highly substituted allylic, homoallylic, and alkenyl alcohols

Herein we report the palladium-catalyzed isomerization of highly substituted allylic alcohols and alkenyl alcohols by means of a single catalytic system. The operationally simple reaction protocol is applicable to a broad range of substrates and displays a wide functional group tolerance, and the products are usually isolated in high chemical yield. Experimental and computational mechanistic investigations provide complementary and converging evidence for a chain-walking process consisting of repeated migratory insertion/β-H elimination sequences. Interestingly, the catalyst does not dissociate from the substrate in the isomerization of allylic alcohols, whereas it disengages during the isomerization of alkenyl alcohols when additional substituents are present on the alkyl chain.

Arylethyne bromoboration-Negishi coupling route to E- Or Z-aryl-substituted trisubstituted alkenes of ≥ 98% isomeric purity. New horizon in the highly selective synthesis of trisubstituted alkenes

The hitherto unprecedented palladiumcatalyzed cross-coupling of (Z)-β-bromo-β-arylethenylboranes can be made to proceed satisfactorily through (1) the use of highly catalytically active bis(tri-tert-butylphosphine) palladium or dichloro[N,N-bis-(2,6-diisopropylphenyl)imidazol-2-yl](m- chloropyridine)palladium and (2) conversion of the dibromoboryl group to the (pinacol)boryl group. Thus, a wide variety of carbon groups can be used to substitute bromine in ≥ 98% stereo- and regioselectivity, while suppressing the otherwise dominant β-debromoboration. Together with the alkylethyne-based protocols, the alkyne bromoboration-Negishi coupling tandem process has emerged as the most widely applicable and highly selective route to trisubstituted alkenes including those that are otherwise difficult to access.