Pentafluorophenylboronic acid

Base Information

• Chemical Name: Pentafluorophenylboronic acid
• CAS No.: 1582-24-7
• Molecular Formula: C6H2BF5O2
• Molecular Weight: 211.884
• Hs Code.: 29319090
• European Community (EC) Number: 627-867-3
• DSSTox Substance ID: DTXSID00379743
• Nikkaji Number: J874.836E
• Wikidata: Q72499838
• Mol file: 1582-24-7.mol

Synonyms:1582-24-7;Pentafluorophenylboronic acid;2,3,4,5,6-PENTAFLUOROBENZENEBORONIC ACID;Perfluorophenylboronic acid;2,3,4,5,6-PENTAFLUOROPHENYLBORONIC ACID;Pentafluorobenzeneboronic acid;(pentafluorophenyl)boronic acid;(2,3,4,5,6-pentafluorophenyl)boronic Acid;BORONIC ACID, (PENTAFLUOROPHENYL)-;MFCD01074663;Pentafluorophenylboronicacid;C6H2BF5O2;Pentafluoroboronic acid;BORONIC ACID, B-(2,3,4,5,6-PENTAFLUOROPHENYL)-;perfluorophenylboronic?acid;SCHEMBL125669;DTXSID00379743;AMY17892;BBL101329;STL555125;AKOS005175091;AB08108;CS-W013176;GS-6218;SY029868;BB 0261400;FT-0609325;P1904;J-506847

Chemical Property of Pentafluorophenylboronic acid

Chemical Property:

• Vapor Pressure: 0.0166mmHg at 25°C
• Melting Point: 176-179°C
• Refractive Index: 1.429
• Boiling Point: 244 °C at 760 mmHg
• PKA: 6.13±0.58(Predicted)
• Flash Point: 101.4 °C
• PSA: 40.46000
• Density: 1.61g/cm³
• LogP: 0.06190
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with alcohols, acetonitrile and dichloromethane.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 212.0068003
• Heavy Atom Count: 14
• Complexity: 191

Purity/Quality:

99.9% ^*data from raw suppliers

2,3,4,5,6-PentafluorobenzeneboronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C(=C(C(=C1F)F)F)F)F)(O)O
• Uses: 2,3,4,5,6-Pentafluorobenzeneboronic acid is utilized in the palladium-catalyzed Suzuki reaction to synthesize several cross-coupled aromatic compounds, for example bis(pentafluorophenyl)-substituted thiophene and selenophene derivatives. It serves as an intermediate and raw material in pharmaceutical and chemical industry. It is also used in dyes and pigments. It can be used to prepare cyclic boronates of bifunctional compounds. Reactant for:Preparation of phenylboronic catechol esters as promising anion receptors for polymer electrolytesPreparation of biaryls via palladium-catalyzed homocoupling reactionPrepartion of quaternary a,a-heterodiaryl carboxylic esters via rhodium-catalyzed cross-couplingC-C cross-coupling reactions suzuki reaction

Technology Process of Pentafluorophenylboronic acid

There total 22 articles about Pentafluorophenylboronic 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: 99.0%

Trimethyl borate (121-43-7,63156-11-6) + Pentafluorobenzene (363-72-4) → pentafluorophenylboronic acid (1582-24-7)

Guidance literature:

Pentafluorobenzene; With isopropylmagnesium chloride; In tetrahydrofuran; toluene; at -10 - 10 ℃; for 4h; Inert atmosphere; Industrial scale;

Trimethyl borate; In tetrahydrofuran; toluene; for 4h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere; Industrial scale;

Reference yield: 95.2%

Trimethyl borate (121-43-7,63156-11-6) + bromopentafluorobenzene (344-04-7) → pentafluorophenylboronic acid (1582-24-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -30 ℃; Temperature; Flow reactor;

Reference yield: 89.0%

tris(pentafluorophenyl)borate (1109-15-5) → bis(pentafluorophenyl)borinic acid (2118-02-7) + pentafluorophenylboronic acid (1582-24-7)

Guidance literature:

upstream raw materials:

dichloro(pentafluorophenyl)borane

tri-n-propyl borate

bromopentafluorobenzene

(pentafluorophenyl)trimethyltin

Downstream raw materials:

2,3,4,5,6-pentafluoro-4'-methylbiphenyl

2-(pentafluorophenyl)-tetrafluoro-1,3,2-benzodioxaborole

1-deutero-2,3,4,5,6-pentafluorobenzene

Pentafluorobenzene

Refernces

• 1、 Fischer, Malte,Schmidtmann, Marc. "B(C6F5)3- And HB(C6F5)2-mediated transformations of isothiocyanates". supporting information. p. 6205 - 6208. Retrieved 2020/06/22.
• 2、 -. "Method for preparing 2,3,4,5,6-pentafluorophenol". Paragraph 0100-0102. . Retrieved 2017/08/29.