109863-08-3

Basic information

• Product Name: 1,3,2-Dioxaborolane, 2-(1-cyclohexen-1-yloxy)-4,4,5,5-tetramethyl-
• CAS NO: 109863-08-3
• Molecular Formula: C12H21BO3
• Molecular Weight: 224.108
• Mol File: 109863-08-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,3,2-Dioxaborolane, 2-(1-cyclohexen-1-yloxy)-4,4,5,5-tetramethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2-Dioxaborolane, 2-(1-cyclohexen-1-yloxy)-4,4,5,5-tetramethyl-(109863-08-3)
• EPA Substance Registry System: 1,3,2-Dioxaborolane, 2-(1-cyclohexen-1-yloxy)-4,4,5,5-tetramethyl-(109863-08-3)

Safety Data

• Hazardous Substances Data: 109863-08-3(Hazardous Substances Data)

Usage

Type of compound

Boronic ester

Structural features

Contains a cyclic ether group
Four methyl substituents on the boron atom

Applications

Organic synthesis
Reagent for Suzuki-Miyaura coupling reactions (formation of carbon-carbon bonds)

Key precursor in the production of

a. Pharmaceuticals
b. Agrochemicals
c. Materials science products

Potential applications

Development of new materials and technologies due to unique chemical structure and reactivity

Upstream product

• 930-68-7 cyclohexenone 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 35365-19-6 2-iodocyclohexanone 

Downstream Products

• 13161-18-7 2-[hydroxy(phenyl)methyl]cyclohexanone 
• 42052-56-2 (+/-)-(S,R)-2-[(hydroxy)(phenyl)methyl]cyclohexanone 

Relevant articles and documents

Progressing the Frustrated Lewis Pair Abilities of N-Heterocyclic Carbene/GaR3Combinations for Catalytic Hydroboration of Aldehydes and Ketones

Exploiting the steric incompatibility of the tris(alkyl)gallium GaR3 (R = CH2SiMe3) and the bulky N-heterocyclic carbene (NHC) 1,3-bis(tert-butyl)imidazol-2-ylidene (ItBu), here we report the B-H bond activation of pinacolborane (HBPin), which has led to

Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation

The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.