2,3,4,6-Tetrafluorophenylboronic acid

Base Information

• Chemical Name: 2,3,4,6-Tetrafluorophenylboronic acid
• CAS No.: 511295-00-4
• Molecular Formula: C6H3BF4O2
• Molecular Weight: 193.893
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID60382551
• Nikkaji Number: J3.298.778H
• Wikidata: Q72505223
• Mol file: 511295-00-4.mol

Synonyms:511295-00-4;2,3,4,6-Tetrafluorophenylboronic acid;(2,3,4,6-tetrafluorophenyl)boronic Acid;2,3,4,6-tetrafluorobenzeneboronic acid;BORONIC ACID, (2,3,4,6-TETRAFLUOROPHENYL)-;SCHEMBL2554608;DTXSID60382551;MFCD04039309;AKOS015853425;AB17323;(2,3,4,6-tetrafluorophenyl)boronicAcid;AS-63873;CS-0132244;FT-0761284;E81572;2,3,4,6-Tetrafluorophenylboronic acid, >=95%;[2,3,4,6-tetrakis(fluoranyl)phenyl]boronic acid;A828454

Chemical Property of 2,3,4,6-Tetrafluorophenylboronic acid

Chemical Property:

• Vapor Pressure: 0.0166mmHg at 25°C
• Melting Point: 121-123°C
• Refractive Index: 1.446
• Boiling Point: 244 °C at 760 mmHg
• Flash Point: 101.4 °C
• PSA: 40.46000
• Density: 1.53 g/cm³
• LogP: -0.07720
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 194.0162221
• Heavy Atom Count: 13
• Complexity: 182

Purity/Quality:

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

2,3,4,6-Tetrafluorophenylboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Useful:

• Canonical SMILES: B(C1=C(C(=C(C=C1F)F)F)F)(O)O
• Uses: (2,3,4,6-Tetrafluorophenyl)boronic acid is a useful reactant for Suzuki-?Miyaura Coupling when paired along with a PAd3-?Pd catalyst.

Technology Process of 2,3,4,6-Tetrafluorophenylboronic acid

There total 2 articles about 2,3,4,6-Tetrafluorophenylboronic 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: 73.0%

Trimethyl borate (121-43-7,63156-11-6) + 1,2,3,5-tetrafluorobenzene (2367-82-0) → 2,3,4,6-tetrafluorophenyl(dihydroxy)borane (511295-00-4)

Guidance literature:

With n-butyllithium; In diethyl ether; hexane; n-BuLi (2.5 M in hexane) was dropped to Et2O soln. of F-compd. (-70 °C, 1 h stirring), mixt. was added to pre-cooled (-60 °C) soln. of 2.5 equiv. of B(OMe)3 in Et2O, stirring for 1 h at -60 °C, warming to 20 ° C within 1 h; hydrolysis with 10 % HCl, org. layer was sepd., aq. layer was twice extd. with ether, extracts were combined, dried with MgSO4, evapd. under vac., solid was recrystd. from hot toluene, elem. anal.;

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

Reference yield:

C4H10O2*C14H8BF8O2(1-)*Li(1+) → (2,3,4,6-C6HF4)2BOH + 2,3,4,6-tetrafluorophenyl(dihydroxy)borane (511295-00-4)

Guidance literature:

With hydrogenchloride; water;

DOI:10.1135/cccc20081681

Reference yield: 99.0%

water-d2 (7789-20-0) + 2,3,4,6-tetrafluorophenyl(dihydroxy)borane (511295-00-4) → 1-deutero-2,3,4,6-tetrafluorobenzene

Guidance literature:

With pyridine; In pyridine; water-d2; B-compd. was added to py-D2O mixt. at 0 °C, heating in an NMR tube within 1-2 min, 100 °C, 15 min; monitored by (19)F NMR; Kinetics;

DOI:10.1002/1521-3749(200213)628:13<2834::AID-ZAAC2834>3.0.CO;2-2

upstream raw materials:

Trimethyl borate

1,2,3,5-tetrafluorobenzene

Downstream raw materials:

1,2,3,5-tetrafluorobenzene

Refernces

• 1、 Frohn,Adonin,Bardin,Starichenko. "Polyfluoroorganoboron-oxygen compounds. 1: Polyfluorinated aryl(dihydroxy)boranes and tri(aryl)boroxins". . p. 2827 - 2833. Retrieved 2008/10/08.