251928-63-9

Basic information

• Product Name: 2-(2-cyclohexylideneethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(2-cyclohexylideneethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 251928-63-9
• Molecular Weight: 236.162
• Mol File: 251928-63-9.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2-(2-cyclohexylideneethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-cyclohexylideneethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(251928-63-9)
• EPA Substance Registry System: 2-(2-cyclohexylideneethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(251928-63-9)

Safety Data

• Hazardous Substances Data: 251928-63-9(Hazardous Substances Data)

Upstream product

• 5664-20-0 vinylidenecyclohexane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1192-37-6 methylenecyclohexane 
• 6318-49-6 1-vinylcyclohexyl acetate 
• 73183-34-3 bis(pinacol)diborane 
• 695-12-5 vinylcyclohexane 
• 1940-19-8 1-vinylcyclohexanol 
• 932-89-8 2-cyclohexylidene ethanol 
• 78-27-3 1-Ethynylcyclohexan-1-ol 

Downstream Products

• 1447730-79-1 1-(trifluoromethoxy)-4-(1-vinylcyclohexyl)benzene 
• 1447730-78-0 1-(2-cyclohexylideneethyl)-4-(trifluoromethoxy)benzene 

Relevant articles and documents

Practical Synthesis of Allyl, Allenyl, and Benzyl Boronates through SN1′-Type Borylation under Heterogeneous Gold Catalysis

Efficient borylation of sp3 C-O bonds by supported Au catalysts is described. Au nanoparticles supported on TiO2 showed high activity under mild conditions employing low catalyst loading conditions without the aid of any additives, such as phosphine and bases. A variety of allyl, propargyl, and benzyl substrates participated in the heterogeneously catalyzed reactions to furnish the corresponding allyl, allenyl, and benzyl boronates in high yields. Besides, Au/TiO2 was also effective for the direct borylation of allylic and benzylic alcohols. A mechanistic investigation based on a Hammett study and control experiments revealed that sp3 C-O bond borylation over supported Au catalysts proceeded through SN1′-type mechanism involving the formation of a carbocationic intermediate. The high activity, reusability, and environmental compatibility of the supported Au catalysts as well as the scalability of the reaction system enable the practical synthesis of valuable organoboron compounds.

Palladium-Catalyzed Oxidative Borylation of Allylic C-H Bonds in Alkenes

This communication describes an efficient palladium pincer complex-catalyzed allylic C-H borylation of alkenes. The transformation exhibits high regio- and stereoselectivity with a variety of linear alkenes. A synthetically useful feature of this allylic C-H borylation method is that all allyl-Bpin products can be isolated in usually high yields. Preliminary mechanistic studies indicate that this C-H borylation reaction proceeds via Pd(IV) pincer complex intermediates.

Regioselective copper-catalyzed carboxylation of allylboronates with carbon dioxide

In the presence of a Cu(I)/NHC catalyst, the reactions of allylboronic pinacol esters with CO2 (1 atm) are highly regioselective, giving exclusively the more substituted β,γ-unsaturated carboxylic acids in most cases. A diverse array of substituted carboxylic acids can be prepared via this method, including compounds featuring all-carbon quaternary centers.