1218790-09-0

Basic information

• Product Name: trans-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane
• Synonyms: trans-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane;trans-Cyclohexane-1,2-diboronic acid, pinacol ester;(1R,2R)-rel-1,2-Bis(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)cyclohexane
• CAS NO: 1218790-09-0
• Molecular Formula: C18H34B2O4
• Molecular Weight: 336.08216
• Mol File: 1218790-09-0.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: trans-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: trans-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane(1218790-09-0)
• EPA Substance Registry System: trans-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane(1218790-09-0)

Safety Data

• Hazardous Substances Data: 1218790-09-0(Hazardous Substances Data)

Usage

General Description

Trans-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane is a chemical compound that has potential relevance in a variety of scientific research areas. Its systematic name is Cyclohexane, 1,2-bis[4,4,5,5-tetramethyl-2-(1,3,2-dioxaborolan-2-yl)], and it belongs to the class of organometallic compounds. The molecule consists of a cyclohexane ring with two tetramethyl-1,3,2-dioxaborolanyl groups attached in a trans configuration. Currently, its primary use is in the field of chemical synthesis, particularly in the development of organic electroluminescent compounds and pharmaceuticals. The compound is appreciated for its stability, which makes it an attractive choice for various laboratory applications.

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 110-83-8 cyclohexene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1687-30-5 cyclohexane-1,2-dicarboxylic acid 
• 66977-99-9 6-bromo-1-hexyne 
• 928-90-5 5-hexyl-1-ol 
• 197313-32-9 (E)-2-(6-chlorohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1301680-12-5 2-[(1E)-but-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 7429-37-0 trans-1,2-dibromocyclohexane 
• 108-85-0 1-bromocyclohexane 

Downstream Products

• 57794-08-8 (1S,2S)-trans-1,2-Cyclohexanediol 
• 1072-86-2 (1R,2R)-trans-1,2-cyclohexanediol 
• 25712-33-8 anti-cyclohexane-1,2-diyldimethanol 
• 1792-81-0 cis-1,2-cyclohexane 

Relevant articles and documents

A site-selective and stereospecific cascade Suzuki-Miyaura annulation of alkyl 1,2-bisboronic esters and 2,2′-dihalo 1,1′-biaryls

A cascade Suzuki-Miyaura cross-coupling giving rise to 9,10-dihydrophenanthrenes has been developed. Using biaryls with unsymmetrical substitution-pattern full site-selectivity was observed. Furthermore, this cross-coupling of an alkyl 1,2-bisboronic pinacol ester proceeds through the challenging coupling of a secondary boronate with complete stereoretention.

Construction of Silicon-Containing Seven-Membered Rings by Catalytic [4 + 2 + 1] Cycloaddition through Rhodium Silylenoid

A rhodium-catalyzed [4 + 2 + 1] cycloaddition involving 1,3-diene, alkyne, and silylene to afford silicon-containing seven-membered rings was established. In the presence of a rhodium catalyst bearing bis(diphenylphosphino)methane (DPPM), nona-1,3-dien-8-yne derivatives reacted efficiently at 80-110 °C with boryl(isopropoxy)silane or boryl(diethyamino)silane, which reacts as the synthetic equivalent of silylene, to afford 1-silacyclohepta-2,5-dienes (2,5-dihydro-1H-silepines). Regiodivergent and chemo- and stereoselective functionalization of the seven-membered nonconjugated diene was achieved by hydroboration mediated by Cs2CO3 or an iridium catalyst.

Vicinal Diboration of Alkyl Bromides via Tandem Catalysis

Vicinal diboration of alkyl bromides via tandem catalysis is reported. The reported reaction exhibits a broad substrate scope, good functional group compatibility, and regioselectivity. Moreover, it shows good practicality due to the easy accessibility of alkyl bromides in combination with diverse transformations of diboronates. Mechanism study indicates that terminal alkenes are generated selectively through nickel-catalyzed dehydrohalogenation of alkyl bromides followed by base/MeOH promoted diboration process to provide 1,2-diboration products.