4-CYANO-2-FLUOROPHENYLBORONIC ACID

Base Information

• Chemical Name: 4-CYANO-2-FLUOROPHENYLBORONIC ACID
• CAS No.: 1150114-77-4
• Molecular Formula: C7H5BFNO2
• Molecular Weight: 164.932
• Hs Code.: 2931900090
• Mol file: 1150114-77-4.mol

Synonyms:4-CYANO-2-FLUOROPHENYLBORONIC ACID;4-Cyano-2-fluorobenzeneboronic acid 98%

Chemical Property of 4-CYANO-2-FLUOROPHENYLBORONIC ACID

Chemical Property:

• PSA: 64.25000
• LogP: -0.62282
• Storage Temp.: 2-8°C

Purity/Quality:

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

4-Cyano-2-fluorophenylboronic acid ^*data from reagent suppliers

Safty Information:

• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Cyano-2-fluorobenzeneboronic acid is used an active pharmaceutical intermediate.

Technology Process of 4-CYANO-2-FLUOROPHENYLBORONIC ACID

There total 2 articles about 4-CYANO-2-FLUOROPHENYLBORONIC 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: 55.0%

Triisopropyl borate (5419-55-6) + 3-fluoro-4-iodo-benzonitrile (887266-99-1) + isopropylmagnesium chloride (1068-55-9) → (4-cyano-2-fluorophenyl)boronic acid (1150114-77-4)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; diethyl ether; water; ethyl acetate;

Reference yield:

Triisopropyl borate (5419-55-6) + 3-fluoro-4-iodo-benzonitrile (887266-99-1) → (4-cyano-2-fluorophenyl)boronic acid (1150114-77-4)

Guidance literature:

3-fluoro-4-iodo-benzonitrile; With isopropylmagnesium chloride; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 3.25h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; diethyl ether; at 20 ℃; for 0.333333h;

DOI:10.1021/acs.jmedchem.8b01544

Reference yield: 90.0%

(4-cyano-2-fluorophenyl)boronic acid (1150114-77-4) + 4-cyano-3-iodo-5-(morpholin-4-yl)thiophene-2-carboxylic acid ethyl ester (1276553-18-4) → ethyl 4-cyano-3-(4-cyano-2-fluorophenyl)-5-morpholinothiophene-2-carboxylate (1276553-17-3)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; cesium fluoride; In 1,4-dioxane; water; toluene; at 85 ℃; for 2h; Inert atmosphere;

DOI:10.1021/op100286g

upstream raw materials:

Triisopropyl borate

3-fluoro-4-iodo-benzonitrile

isopropylmagnesium chloride

Downstream raw materials:

ethyl 4-cyano-3-(4-cyano-2-fluorophenyl)-5-morpholinothiophene-2-carboxylate

4-cyano-3-(4-cyano-2-fluorophenyl)-5-morpholinothiophene-2-carboxylic acid

4-(4-cyano-2-fluorophenyl)-2-morpholino-5-((1H)-1,2,4-triazol-5-yl)thiophene-3-carbonitrile

4-cyano-3-(4-cyano-2-fluorophenyl)-5-morpholinothiophene-2-carboxamide

Refernces

• 1、 -. "HETEROCYCLICALLY SUBSTITUTED ARYL COMPOUNDS AS HIF INHIBITORS". Paragraph 1211; 1212; 1213. . Retrieved 2013/08/14.