251928-76-4

Basic information

• Product Name: 2-(1-cyclohexylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(1-cyclohexylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 251928-76-4
• Molecular Weight: 236.162
• Mol File: 251928-76-4.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 2-(1-cyclohexylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-cyclohexylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(251928-76-4)
• EPA Substance Registry System: 2-(1-cyclohexylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(251928-76-4)

Safety Data

• Hazardous Substances Data: 251928-76-4(Hazardous Substances Data)

Usage

Boron-containing compound

The compound contains a boron atom, which is a key feature for its use in organic synthesis reactions.

Cyclohexylvinyl group

A vinyl group (carbon-carbon double bond) attached to a cyclohexane ring, which allows for the formation of carbon-carbon bonds.

Tetramethyl-1,3,2-dioxaborolane moiety

A boron-containing ring structure with four methyl groups (carbon-hydrogen groups) attached to it, which provides stability and reactivity to the compound.

Commonly used as a boron source in organic synthesis

The compound is often utilized as a source of boron in the synthesis of organic compounds.

Used in cross-coupling reactions

The compound is often used in reactions such as Suzuki-Miyaura and Stille couplings, which are used to form carbon-carbon bonds.

Facilitates the construction of complex organic molecules

The compound aids in the formation of complex organic molecules by providing a source of boron.

Valuable precursor for creating functionalized organic compounds

The presence of the boron atom in the compound makes it a useful starting material for the synthesis of a wide range of functionalized organic compounds.

Applications in pharmaceuticals, agrochemicals, and materials science

The compound has a wide range of potential uses in various fields, including the production of drugs, pesticides, and other materials.

Upstream product

• 5664-20-0 vinylidenecyclohexane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 85970-80-5 1-bromo-1-cyclohexylethylene 
• 931-48-6 2-cyclohexylacetylene 
• 73183-34-3 bis(pinacol)diborane 
• 16722-09-1 trimethylsilyloxirane 
• 87100-15-0 cyclohexylboronic acid pinacol ester 
• 52470-92-5 1,1-Dibromomethylcyclohexane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 75-11-6 diiodomethane 
• 1512864-19-5 2,2'-(cyclohexylmethylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 78-27-3 1-Ethynylcyclohexan-1-ol 

Downstream Products

• 63167-00-0 (R)-N-benzyl-1-cyclohexylethylamine 
• 1202245-69-9 1‐cyclohexylethen-1-ylboronic acid 
• 894771-04-1 (R)-2-(1-cyclohexyl-ethyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 

Relevant articles and documents

Cyclic (Alkyl)(amino)carbene Ligands Enable Cu-Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes**

Regioselective hydrofunctionalization of alkynes represents a straightforward route to access alkenyl boronate and silane building blocks. In previously reported catalytic systems, high selectivity is achieved with a limited scope of substrates and/or rea

Electrochemical Hydroboration of Alkynes

Herein we reported the electrochemical hydroboration of alkynes by using B2Pin2 as the boron source. This unprecedented reaction manifold was applied to a broad range of alkynes, giving the hydroboration products in good to excellent yields without the need of a metal catalyst or a hydride source. This transformation relied on the possible electrochemical oxidation of an in situ formed borate. This anodic oxidation performed in an undivided cell allowed the formation of a putative boryl radical, which reacted on the alkyne.

Reaction Pathways and Redox States in α-Selective Cobalt-Catalyzed Hydroborations of Alkynes

Cobalt(II) alkyl complexes supported by a monoanionic NNN pincer ligand are pre-catalysts for the regioselective hydroboration of terminal alkynes, yielding the Markovnikov products with α:β-(E) ratios of up to 97:3. A cobalt(II) hydride and a cobalt(II) vinyl complex appear to determine the main reaction pathway. In a background reaction the highly reactive hydrido species specifically converts to a coordinatively unsaturated cobalt(I) complex which was found to re-enter the main catalytic cycle.