2,4,6-Trifluorophenylboronic acid

Base Information

• Chemical Name: 2,4,6-Trifluorophenylboronic acid
• CAS No.: 182482-25-3
• Molecular Formula: C6H4BF3O2
• Molecular Weight: 175.903
• Hs Code.: 29319090
• European Community (EC) Number: 681-558-8
• DSSTox Substance ID: DTXSID90381390
• Nikkaji Number: J1.853.707I
• Wikidata: Q72513252
• ChEMBL ID: CHEMBL91770
• Mol file: 182482-25-3.mol

Synonyms:Boronicacid, (2,4,6-trifluorophenyl)- (9CI);(2,4,6-Trifluorophenyl)boronic acid;

Chemical Property of 2,4,6-Trifluorophenylboronic acid

Chemical Property:

• Appearance/Colour: Off-white cryst.
• Vapor Pressure: 0.00444mmHg at 25°C
• Melting Point: 228-235 °C(lit.)
• Refractive Index: 1.465
• Boiling Point: 236 °C at 760 mmHg
• PKA: 8.26±0.58(Predicted)
• Flash Point: 96.5 °C
• PSA: 40.46000
• Density: 1.44 g/cm³
• LogP: -0.21630
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 176.0256440
• Heavy Atom Count: 12
• Complexity: 146

Purity/Quality:

99% ^*data from raw suppliers

2,4,6-Trifluorophenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-22
• Safety Statements: 26-36-36/37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=C(C=C1F)F)F)(O)O
• Uses: suzuki reaction Reactant involved in:Synthesis of phenylboronic catechol estersSuzuki-Miyaura coupling reactions with aryl chlorides and unstable polyfluorophenylEnantioselective borane reduction of trifluoroacetophenoneTransmetalation

Technology Process of 2,4,6-Trifluorophenylboronic acid

There total 5 articles about 2,4,6-Trifluorophenylboronic 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: 81.8%

Triisopropyl borate (5419-55-6) + 1,3,5-trifluorobenzene (372-38-3) → 2,4,6-trifluorophenylboronic acid (182482-25-3)

Guidance literature:

1,3,5-trifluorobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -50 ℃; for 1.5h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; hexane; at -50 ℃; for 1h; Inert atmosphere;

With hydrogenchloride; water; In tetrahydrofuran; hexane; at 20 ℃; Temperature; Inert atmosphere;

Reference yield: 73.6%

Trimethyl borate (121-43-7,63156-11-6) + 1,3,5-trifluorobenzene (372-38-3) → 2,4,6-trifluorophenylboronic acid (182482-25-3)

Guidance literature:

1,3,5-trifluorobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -50 ℃; for 1.5h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; hexane; at -50 ℃; for 1h; Inert atmosphere;

With hydrogenchloride; water; In tetrahydrofuran; hexane; at 20 ℃; Temperature; Inert atmosphere;

Reference yield: 63.0%

Trimethyl borate (121-43-7,63156-11-6) + 2,4,6-trifluorobromobenzene (2367-76-2) → 2,4,6-trifluorophenylboronic acid (182482-25-3)

Guidance literature:

With n-butyllithium; In diethyl ether; hexane; n-BuLi (2.5 M, hexane) was added to ethereal soln. of C6F3BrH2 at -60 °C, keeping at this temp., 1.5 equiv. of cold (-70 °C) B(OMe)3 was added in ether, mixt. was stirred for 1 h at -60 °C, warmed up to 20 °C within 1 h; poured into 5 % HCl, org. layer was sepd., aq. layer was twice extd. with ether, extracts were combined, dried with MgSO4, evapn., recrystn. from hot toluene, elem. anal.;

DOI:10.1002/1521-3749(200213)628:13<2827::AID-ZAAC2827>3.0.CO;2-N

upstream raw materials:

2,4,6-trifluorobromobenzene

Trimethyl borate

1,3,5-trifluorobenzene

Triisopropyl borate

Downstream raw materials:

1,3,5-trifluorobenzene

[Pd(2,4,6-trifluorophenyl)(C₆H₄-4-OMe)(N,N,N',N'-tetramethylethylenediamine)]

trans-Pd(C₆F₅)(2,4,6-C₆F₃H₂)(PEt₃)2

Pt(C₆H₂F₃-2,4,6)(Ph)(1,5-cyclooctadiene)

Refernces

• 1、 Ting, Richard,Harwig, Curtis W.,Lo, Justin,Li, Ying,Adam, Michael J.,Ruth, Thomas J.,Petrin, David M.. "Substituent effects on aryltrifluoroborate solvolysis in water: Implications for Suzuki-Miyaura coupling and the design of stable 18F-labeled aryltrifluoroborates for use in PET imaging". . p. 4662 - 4670. Retrieved 2008/09/20.
• 2、 Frohn,Franke,Fritzen,Bardin. "(Fluoroorgano)fluoroboranes and -fluoroborates I: Synthesis and spectroscopic characterization of potassium fluoroaryltrifluoroborates and fluoroaryldifluoroboranes". . p. 127 - 135. Retrieved 2007/10/03.