TRANS-2-(4-FLUOROPHENYL)VINYLBORONIC ACID

Base Information

• Chemical Name: TRANS-2-(4-FLUOROPHENYL)VINYLBORONIC ACID
• CAS No.: 214907-24-1
• Molecular Formula: C8H8 B F O2
• Molecular Weight: 165.96
• Hs Code.: 2931900090
• Mol file: 214907-24-1.mol

Synonyms:Boronicacid, [2-(4-fluorophenyl)ethenyl]- (9CI); [2-(4-Fluorophenyl)vinyl]boronic acid

Chemical Property of TRANS-2-(4-FLUOROPHENYL)VINYLBORONIC ACID

Chemical Property:

• Vapor Pressure: 0.000205mmHg at 25°C
• Melting Point: 182-186 °C(lit.)
• Refractive Index: 1.565
• Boiling Point: 313.9°Cat760mmHg
• PKA: 9.53±0.43(Predicted)
• Flash Point: 143.6°C
• PSA: 40.46000
• Density: 1.228g/cm³
• LogP: 0.85090
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

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

trans-2-(4-Fluorophenyl)vinylboronic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Reactant for:Suzuki-Miyaura coupling reactionsPreparation of biologically and pharmacologically active moleculesConjugate addition reactions

Technology Process of TRANS-2-(4-FLUOROPHENYL)VINYLBORONIC ACID

There total 5 articles about TRANS-2-(4-FLUOROPHENYL)VINYLBORONIC 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:

1-ethynyl-4-fluorobenzene (766-98-3) + benzo[1,3,2]dioxaborole (274-07-7) → [2-(4-fluorophenyl)vinyl]boronic acid (214907-24-1)

Guidance literature:

In tetrahydrofuran; at 65 ℃; for 24h;

DOI:10.1002/anie.201611006

Reference yield:

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(4-fluorophenyl)ethene → [2-(4-fluorophenyl)vinyl]boronic acid (214907-24-1)

Guidance literature:

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(4-fluorophenyl)ethene; With sodium periodate; In tetrahydrofuran; water; for 0.5h;

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1002/cjoc.202000579

Reference yield:

1-ethynyl-4-fluorobenzene (766-98-3) + dibromoborane dimethylsulfide (55671-55-1) + water (7732-18-5) → [2-(4-fluorophenyl)vinyl]boronic acid (214907-24-1)

Guidance literature:

1-ethynyl-4-fluorobenzene; dibromoborane dimethylsulfide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

water; In diethyl ether; dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol4035897

upstream raw materials:

1-ethynyl-4-fluorobenzene

dibromoborane dimethylsulfide

water

benzo[1,3,2]dioxaborole

Downstream raw materials:

C₂₂H₂₆FN₃O₃

C₂₁H₂₅FN₄O₃

C₁₃H₁₃BFNO₄

Refernces

• 1、 Liu, Shiwen,Meng, Lingling,Zeng, Xiaojun,Hammond, Gerald B.,Xu, Bo. "Synthesis of Acrylonitriles via Mild Base Promoted Tandem Nucleophilic Substitution-Isomerization of α-Cyanohydrin Methanesulfonates". supporting information. p. 913 - 917. Retrieved 2021/04/05.
• 2、 Corless, Victoria B.,Holownia, Aleksandra,Foy, Hayden,Mendoza-Sanchez, Rodrigo,Adachi, Shinya,Dudding, Travis,Yudin, Andrei K.. "Synthesis of α-Borylated Ketones by Regioselective Wacker Oxidation of Alkenylboronates". supporting information. p. 5300 - 5303. Retrieved 2018/09/12.