(2,3,4,5-tetrafluorophenyl)boronic Acid

Base Information

• Chemical Name: (2,3,4,5-tetrafluorophenyl)boronic Acid
• CAS No.: 179923-32-1
• Molecular Formula: C6H3BF4O2
• Molecular Weight: 193.893
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID00382550
• Nikkaji Number: J754.654H
• Wikidata: Q72505222
• Mol file: 179923-32-1.mol

Synonyms:179923-32-1;(2,3,4,5-tetrafluorophenyl)boronic Acid;2,3,4,5-Tetrafluorophenylboronic acid;2,3,4,5-tetrafluorobenzeneboronic acid;Boronic acid, (2,3,4,5-tetrafluorophenyl)-;tetrafluorophenylboronic acid;SCHEMBL2993734;DTXSID00382550;MFCD04039308;AKOS015914331;2,3,4,5-Tetrafluorophenylboranic acid;AB17320;(2,3,4,5-tetrafluorophenyl)boronicAcid;AS-66439;CS-0175111;F87196;2,3,4,5-Tetrafluorophenylboronic acid, >=95%;EN300-3172239;A812501

Chemical Property of (2,3,4,5-tetrafluorophenyl)boronic Acid

Chemical Property:

• Vapor Pressure: 0.00737mmHg at 25°C
• Melting Point: 264-269 °C
• Refractive Index: 1.446
• Boiling Point: 257.6 °C at 760 mmHg
• PKA: 6.33±0.58(Predicted)
• Flash Point: 109.6 °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

2,3,4,5-tetrafluorobenzeneboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=C(C(=C1F)F)F)F)(O)O
• Uses: Reactant for:Base-catalyzed hydrodeboration and deuterodeborationCatalyst for:Amidation reactions

Technology Process of (2,3,4,5-tetrafluorophenyl)boronic Acid

There total 3 articles about (2,3,4,5-tetrafluorophenyl)boronic 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: 61.0%

Trimethyl borate (121-43-7,63156-11-6) + 1,2,3,4-tetrafluorobenzene (551-62-2) + water (7732-18-5) → 2,3,4,5-tetrafluorophenyl(dihydroxy)borane (179923-32-1)

Guidance literature:

1,2,3,4-tetrafluorobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

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

DOI:10.1002/ejoc.201700621

Reference yield: 22.0%

Trimethyl borate (121-43-7,63156-11-6) + 1,2,3,4-tetrafluorobenzene (551-62-2) → 2,3,4,5-tetrafluorophenyl(dihydroxy)borane (179923-32-1)

Guidance literature:

With n-butyllithium; In diethyl ether; hexane; n-BuLi in 2.5 M hexane soln. was added to ethereal soln. of C6F4H between -70 and -75 °C, 1.5 equiv. of cold (-70 °C) B(OMe)3 soln. was added in ether, mixt. was kept for 1 h below -60 °C, warmedup to 15-18 °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., recrystn. from toluene, elem. anal.;

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

Reference yield:

1,2,3,4-tetrafluorobenzene (551-62-2) → 2,3,4,5-tetrafluorophenyl(dihydroxy)borane (179923-32-1)

Guidance literature:

1,2,3,4-tetrafluorobenzene; With n-butyllithium; In diethyl ether; hexane; at -60 ℃;

With Triisopropyl borate; In diethyl ether; hexane; at -70 ℃;

With hydrogenchloride; In diethyl ether; hexane;

DOI:10.1016/S0022-328X(99)00690-7

upstream raw materials:

1,2,3,4-tetrafluorobenzene

Trimethyl borate

water

Downstream raw materials:

4,4,5,5-tetramethyl-2-(2,3,4,5-tetrafluorophenyl)-1,3,2-dioxaborolane

1,2,3,4-tetrafluorobenzene

4-methyl-2-(2,3,4,5-tetrafluorophenyl)quinoline

[Pd(PPh₃)2(Br)(2-pyridyl-3,4,5,6-tetrafluorophenyl)]

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.