4,4-(DIMETHYLCYCLOHEXENE-1-YL)BORONIC ACID, PINACOL ESTER

Base Information

• Chemical Name: 4,4-(DIMETHYLCYCLOHEXENE-1-YL)BORONIC ACID, PINACOL ESTER
• CAS No.: 859217-67-7
• Molecular Formula: C14H25 B O2
• Molecular Weight: 236.162
• Hs Code.: 2934999090
• Mol file: 859217-67-7.mol

Synonyms:4,4-(DIMETHYLCYCLOHEXENE-1-YL)BORONIC ACID, PINACOL ESTER

Chemical Property of 4,4-(DIMETHYLCYCLOHEXENE-1-YL)BORONIC ACID, PINACOL ESTER

Chemical Property:

• Vapor Pressure: 0.027mmHg at 25°C
• Refractive Index: 1.466
• Boiling Point: 255.024ºC at 760 mmHg
• Flash Point: 108.035ºC
• PSA: 18.46000
• Density: 0.941g/cm3
• LogP: 3.75430
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

4,4-Dimethylcyclohexen-1-ylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4,4-Dimethylcyclohexen-1-ylboronic acid, pinacol ester

Technology Process of 4,4-(DIMETHYLCYCLOHEXENE-1-YL)BORONIC ACID, PINACOL ESTER

There total 4 articles about 4,4-(DIMETHYLCYCLOHEXENE-1-YL)BORONIC ACID, PINACOL ESTER which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 57.0%

trifluoromethanesulfonic acid 4,4-dimethyl-cyclohex-1-enyl ester (98056-47-4) + bis(pinacol)diborane (73183-34-3) → 2-(4,4-dimethylcyclohex-1-ene-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (859217-67-7)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 90 ℃; for 16h; Inert atmosphere;

Reference yield: 52.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + N'-(4,4-dimethylcyclohexylidene)-4-methylbenzene-1-sulfonohydrazide (64692-81-5) → 2-(4,4-dimethylcyclohex-1-ene-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (859217-67-7)

Guidance literature:

N'-(4,4-dimethylcyclohexylidene)-4-methylbenzene-1-sulfonohydrazide; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In hexane; at -78 - 25 ℃; for 3h; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In hexane; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ol401416r

Reference yield:

4,4-dimethylcyclohexane-1-one (4255-62-3) → 2-(4,4-dimethylcyclohex-1-ene-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (859217-67-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 16 h / -78 - 20 °C

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; 1,1'-bis-(diphenylphosphino)ferrocene / 1,4-dioxane / 16 h / 90 °C / Inert atmosphere

With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane;

upstream raw materials:

trifluoromethanesulfonic acid 4,4-dimethyl-cyclohex-1-enyl ester

bis(pinacol)diborane

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

N'-(4,4-dimethylcyclohexylidene)-4-methylbenzene-1-sulfonohydrazide

Downstream raw materials:

4-bromo-2-(4,4-dimethyl-cyclohex-1-enyl)-phenylamine

Refernces

• 1、 Bi, Hong-Yan,Li, Cheng-Jing,Liang, Cui,Mo, Dong-Liang,Wei, Cui. "Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles". supporting information. p. 5815 - 5821. Retrieved 2020/09/21.
• 2、 -. "4-CARBOX PYRAZOLE DERIVATES USEFUL AS ANTI-VIRAL AGENTS". Page/Page column 65. . Retrieved 2010/02/14.