(4-FLUORO-2-FORMYLPHENYL)BORONIC ACID

Base Information

• Chemical Name: (4-FLUORO-2-FORMYLPHENYL)BORONIC ACID
• CAS No.: 825644-26-6
• Molecular Formula: C7H6BFO3
• Molecular Weight: 167.932
• Hs Code.: 2931900090
• Mol file: 825644-26-6.mol

Synonyms:4-Fluoro-2-formylphenylboronic acid;

Chemical Property of (4-FLUORO-2-FORMYLPHENYL)BORONIC ACID

Chemical Property:

• Melting Point: 123-125 °C
• Boiling Point: 341.9±52.0 °C(Predicted)
• PKA: 8.32±0.53(Predicted)
• PSA: 57.53000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: -0.68200
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

4-Fluoro-2-formylphenylboronicacid(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: suzuki reaction

Technology Process of (4-FLUORO-2-FORMYLPHENYL)BORONIC ACID

There total 7 articles about (4-FLUORO-2-FORMYLPHENYL)BORONIC 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: 89.5%

triethyl borate (150-46-9) + 1-bromo-2-(dimethoxymethyl)-4-fluorobenzene (933585-18-3) → (4-fluoro-2-formylphenyl)boronic acid (825644-26-6)

Guidance literature:

1-bromo-2-(dimethoxymethyl)-4-fluorobenzene; With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane; at -75 - -70 ℃;

triethyl borate; In tetrahydrofuran; diethyl ether; hexane; at -70 ℃;

With hydrogenchloride; In tetrahydrofuran; diethyl ether; hexane; water; at -70 - 5 ℃; pH=3;

DOI:10.1016/j.jfluchem.2016.05.001

Reference yield: 77.0%

2-(2-bromo-5-fluorophenyl)-1,3-dioxolane (773094-69-2) → (4-fluoro-2-formylphenyl)boronic acid (825644-26-6)

Guidance literature:

2-(2-bromo-5-fluorophenyl)-1,3-dioxolane; With n-butyllithium; In tetrahydrofuran; hexane; at -74 - -70 ℃; for 1h;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -70 - 15 ℃; for 2h;

With hydrogenchloride; water; In tetrahydrofuran; hexane; at 60 ℃; for 1h; pH=1;

Reference yield: 55.0%

Trimethyl borate (121-43-7,63156-11-6) + 1-bromo-2-(dimethoxymethyl)-4-fluorobenzene (933585-18-3) → (4-fluoro-2-formylphenyl)boronic acid (825644-26-6)

Guidance literature:

1-bromo-2-(dimethoxymethyl)-4-fluorobenzene; With n-butyllithium; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.joc.9b02473

upstream raw materials:

2-(2-bromo-5-fluorophenyl)-1,3-dioxolane

2-bromo-5-fluorobenzaldehyde

triethyl borate

1-bromo-2-(dimethoxymethyl)-4-fluorobenzene

Refernces

• 1、 Chen, Fener,Chen, Xiao-Pan,Deng, Ji,Li, Gen,Li, Guo-Bo,Schofield, Christopher J.,Xiao, You-Cai,Yan, Yu-Hang,Yu, Jun-Lin,Zhu, Kai-Rong,Brem, Jürgen. "Design and enantioselective synthesis of 3-(α-acrylic acid) benzoxaboroles to combat carbapenemase resistance". . p. 7709 - 7712. Retrieved 2021/08/09.
• 2、 Yan, Yu-Hang,Li, Zhao-Feng,Ning, Xiang-Li,Deng, Ji,Yu, Jun-Lin,Luo, Yubin,Wang, Zhenling,Li, Guo,Li, Guo-Bo,Xiao, You-Cai. "Discovery of 3-aryl substituted benzoxaboroles as broad-spectrum inhibitors of serine- and metallo-β-lactamases". supporting information. . Retrieved 2021/04/12.