2-Cyclohexylethenylboronic acid

Base Information

• Chemical Name: 2-Cyclohexylethenylboronic acid
• CAS No.: 37490-33-8
• Molecular Formula: C₈H₁₅BO₂
• Molecular Weight: 154.017
• Hs Code.: 2931900090
• Mol file: 37490-33-8.mol

Synonyms:Boronicacid, (2-cyclohexylethenyl)-, (E)-; Boronic acid, [(1E)-2-cyclohexylethenyl]-(9CI); trans-(2-Cyclohexylethenyl)boronic acid

Chemical Property of 2-Cyclohexylethenylboronic acid

Chemical Property:

• Vapor Pressure: 0.000361mmHg at 25°C
• Melting Point: 106-111 ºC
• Boiling Point: 283.7°C at 760 mmHg
• Flash Point: 125.4°C
• PSA: 40.46000
• Density: 1.078g/cm³
• LogP: 1.13490
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-CyclohexylvinylboronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Reactant for:Pd-catalyzed coupling reactionsChiral palladacycle-catalyzed asymmetric ring-opening reactionAsymmetric Suzuki-Miyaura coupling

Technology Process of 2-Cyclohexylethenylboronic acid

There total 5 articles about 2-Cyclohexylethenylboronic acid 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:

(E)-(2-cyclohexylethen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → (E)-(2-cyclohexylvinyl)boronic acid (57002-01-4,37490-33-8)

Guidance literature:

With sodium periodate; ammonium acetate; In water; acetone; at 20 ℃; for 24h;

DOI:10.1016/j.chempr.2021.10.015

Reference yield:

dibromoborane dimethylsulfide (55671-55-1) + 2-cyclohexylacetylene (931-48-6) + water (7732-18-5) → (E)-(2-cyclohexylvinyl)boronic acid (57002-01-4,37490-33-8)

Guidance literature:

dibromoborane dimethylsulfide; 2-cyclohexylacetylene; In dichloromethane; at 0 - 20 ℃; for 4h;

water; In diethyl ether; for 0.25h; Cooling with ice;

DOI:10.1021/ol501309e

Reference yield:

dibromoborane dimethylsulfide (55671-55-1) + 2-cyclohexylacetylene (931-48-6) → (E)-(2-cyclohexylvinyl)boronic acid (57002-01-4,37490-33-8)

Guidance literature:

dibromoborane dimethylsulfide; 2-cyclohexylacetylene; In dichloromethane; at 0 - 20 ℃; for 4h;

With water; ammonium chloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jacs.5b09773

upstream raw materials:

dibromoborane dimethylsulfide

2-cyclohexylacetylene

water

Downstream raw materials:

(E)-N-(2-cyclohexylvinyl)benzamide

(E)-2-(2-cyclohexylvinyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

5-cyclohexyl-7-(4-nitrophenyl)-1-tosyl-2,3,4,5-tetrahydro-1H-indole

5-cyclohexyl-7-hexyl-1-tosyl-2,3,4,5-tetrahydro-1H-indole

Refernces

• 1、 Bi, Hong-Yan,Liu, Feng-Ping,Liang, Cui,Su, Gui-Fa,Mo, Dong-Liang. "A Tunable Route to Prepare α,β-Unsaturated Esters and α,β-Unsaturated-γ-Keto Esters through Copper-Catalyzed Coupling of Alkenyl Boronic Acids with Phosphorus Ylides". supporting information. p. 1510 - 1516. Retrieved 2018/03/05.
• 2、 Feng, Chao,Loh, Teck-Peng. "Rhodium(III)-catalyzed cross-coupling of alkenylboronic acids and N -pivaloyloxylamides". supporting information. p. 3444 - 3447. Retrieved 2014/07/21.