(4-Amino-3-fluorophenyl)boronic acid

Base Information

• Chemical Name: (4-Amino-3-fluorophenyl)boronic acid
• CAS No.: 494752-42-0
• Molecular Formula: C6H7BFNO2
• Molecular Weight: 154.936
• DSSTox Substance ID: DTXSID60436528
• Nikkaji Number: J1.951.277K
• Wikidata: Q72437284
• Mol file: 494752-42-0.mol

Synonyms:4-amino-3-fluorophenylboronic acid

Chemical Property of (4-Amino-3-fluorophenyl)boronic acid

Chemical Property:

• PSA: 66.48000
• Density: 1.34
• LogP: 0.47090
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 155.0553868
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

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

4-Amino-3-fluorophenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=C(C=C1)N)F)(O)O
• Uses: (4-Amino-3-fluorophenyl)boronic Acid is used in preparation of N-(phenyl)benzenesulfonamides as GPR120 agonists for treatment of GPR120-mediated diabetes.

Technology Process of (4-Amino-3-fluorophenyl)boronic acid

There total 3 articles about (4-Amino-3-fluorophenyl)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: 45.0%

2-(4-bromo-2-fluoro-phenyl)-1,1,1,3,3,3-hexamethyl-disilazane → 4-amino-3-fluoro-phenylboronic acid (494752-42-0)

Guidance literature:

2-(4-bromo-2-fluoro-phenyl)-1,1,1,3,3,3-hexamethyl-disilazane; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃;

With Trimethyl borate; In tetrahydrofuran; diethyl ether; pentane; at -78 ℃;

With hydrogenchloride; In tetrahydrofuran; diethyl ether; pentane; at 20 ℃;

DOI:10.1016/j.tetlet.2003.08.094

Reference yield:

4-bromo-2-fluoroaniline (367-24-8) → 4-amino-3-fluoro-phenylboronic acid (494752-42-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 47 percent / n-BuLi / tetrahydrofuran; hexane / 0 - 20 °C

2.1: t-BuLi / diethyl ether; pentane / -78 °C

2.2: trimethylborate / diethyl ether; tetrahydrofuran; pentane / -78 °C

2.3: 45 percent / HCl / diethyl ether; tetrahydrofuran; pentane / 20 °C

With n-butyllithium; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; hexane; pentane;

DOI:10.1016/j.tetlet.2003.08.094

Reference yield:

4-bromo-2-fluoroaniline (367-24-8) + 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane (201733-56-4) → 4-amino-3-fluoro-phenylboronic acid (494752-42-0)

Guidance literature:

4-bromo-2-fluoroaniline; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane; With potassium acetate; bis-triphenylphosphine-palladium(II) chloride; In dimethyl sulfoxide; at 60 ℃;

With water; In dimethyl sulfoxide;

upstream raw materials:

4-bromo-2-fluoroaniline

2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane

Downstream raw materials:

C₇H₇BFNO₃

C₂₅H₃₁FN₂O₂S

C₃₅H₄₀FN₇O₄

4-amino-3-fluoro-5-iodophenylboronic acid

Refernces

• 1、 -. "ANTIVIRAL AGENTS". Page/Page column 97. . Retrieved 2008/06/13.