2-Cyano-6-fluorophenylboronic acid

Base Information

• Chemical Name: 2-Cyano-6-fluorophenylboronic acid
• CAS No.: 656235-44-8
• Molecular Formula: C7H5BFNO2
• Molecular Weight: 164.93000
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID80477892
• Wikidata: Q82310934
• Mol file: 656235-44-8.mol

Synonyms:656235-44-8;2-cyano-6-fluorophenylboronic acid;(2-cyano-6-fluorophenyl)boronic acid;MFCD09033623;Boronic acid, (2-cyano-6-fluorophenyl)-;SCHEMBL1668130;DTXSID80477892;AMY21978;(2-cyano-6-fluorophenyl)boronicacid;AKOS006330761;AB49390;DS-18085;SY031660;CS-0029541;A867631

Chemical Property of 2-Cyano-6-fluorophenylboronic acid

Chemical Property:

• Boiling Point: 367.7±52.0 °C(Predicted)
• PKA: 7.77±0.58(Predicted)
• PSA: 64.25000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: -0.62282
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 165.0397367
• Heavy Atom Count: 12
• Complexity: 203

Purity/Quality:

98%Min ^*data from raw suppliers

2-Cyano-6-fluorophenylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=CC=C1F)C#N)(O)O
• Uses: 2-Cyano-6-fluorophenylboronic acid

Technology Process of 2-Cyano-6-fluorophenylboronic acid

There total 2 articles about 2-Cyano-6-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: 89.0%

m-Fluorobenzonitrile (403-54-3) → (2-cyano-6-fluorophenyl)boronic acid (656235-44-8)

Guidance literature:

m-Fluorobenzonitrile; With Triisopropyl borate; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -50 - -5 ℃; for 1.5h;

With hydrogenchloride; water; In tetrahydrofuran; hexane; tert-butyl methyl ether; at 20 ℃; for 0.5h;

Reference yield:

C13H17BFNO2 → (2-cyano-6-fluorophenyl)boronic acid (656235-44-8) + tris(2-cyano-6-fluorophenyl)boroxine

Guidance literature:

With hydrogenchloride; In various solvents; at 0 - 23 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1021/jo035184p

Reference yield:

(2-cyano-6-fluorophenyl)boronic acid (656235-44-8) → TPA023B

Guidance literature:

Multi-step reaction with 3 steps

1.1: 88 percent Chromat_. / 1,3-dibromo-5,5-dimethylhydantoin; NaOMe / acetonitrile; methanol / 15 - 25 °C

2.1: hexyllithium / tetrahydrofuran; hexane / 1 h / -25 - -20 °C

2.2: zinc chloride / tetrahydrofuran; hexane / 0.5 h / 0 °C

2.3: 73 percent / Pd₂(dba)3; tBu₃P / tetrahydrofuran / 1 h / 23 °C

3.1: 20 percent / Cs₂CO₃ / Pd; IMes / dioxane / 48 h / 100 °C

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sodium methylate; n-hexyllithium; caesium carbonate; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; acetonitrile; 2.3: Negishi coupling;

DOI:10.1021/jo0507035

upstream raw materials:

m-Fluorobenzonitrile

Downstream raw materials:

2-Bromo-3-fluorobenzamide

2-bromo-3-fluorobenzonitrile

5'-bromo-6,2'-difluorobiphenyl-2-carbonitrile

Refernces

• 1、 Gauthier Jr., Donald R.,Limanto, John,Devine, Paul N.,Desmond, Richard A.,Szumigala Jr., Ronald H.,Foster, Bruce S.,Volante. "Palladium-catalyzed regioselective arylation of imidazo[1,2-b][1,2,4] triazine: Synthesis of an α2/3-selective GABA agonist". . p. 5938 - 5945. Retrieved 2007/10/03.