3,4,5-Trifluorophenylboronic acid

Base Information

• Chemical Name: 3,4,5-Trifluorophenylboronic acid
• CAS No.: 143418-49-9
• Molecular Formula: C6H4BF3O2
• Molecular Weight: 175.903
• Hs Code.: 29163990
• European Community (EC) Number: 604-355-8
• DSSTox Substance ID: DTXSID60370438
• Nikkaji Number: J754.652A
• Wikidata: Q72513243
• Mol file: 143418-49-9.mol

Synonyms:3,4,5-Trifluorophenylboronic acid;143418-49-9;(3,4,5-trifluorophenyl)boronic Acid;3,4,5-Trifluorobenzeneboronic Acid;3,4,5-Trifluorophenyl boronic acid;MFCD02093069;C6H4BF3O2;Boronic acid, (3,4,5-trifluorophenyl)-;BORONIC ACID, B-(3,4,5-TRIFLUOROPHENYL)-;EC 604-355-8;3,4,5-Trifluorophenylboronicacid;AKOS BRN-0138;SCHEMBL177479;DTXSID60370438;3,4,5-Trifluorphenylboronic acid;UHDDEIOYXFXNNJ-UHFFFAOYSA-N;BCP22735;CS-D1006;(3,4,5-trifluorophenyl)boronicAcid;3,4,5-trifluoro-phenylboronic acid;3,4,5-trifluorobenzene boronic acid;AKOS004116551;AB10760;AC-5392;BCP9000265;GS-6729;(3,4,5-trifluoro-phenyl)-boronic acid;Acide (3,4,5-trifluorophenyl)boronique;NCGC00249510-01;SY007885;3,4,5-TRIFLUOROPHENYLBORONIC AICD;AM20060172;FT-0614138;FT-0657731;T2300;EN300-53326;Q-101276;3 pound not4 pound not5-Trifluorophenyl boronic acid;Z798912500;(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride)

Chemical Property of 3,4,5-Trifluorophenylboronic acid

Chemical Property:

• Appearance/Colour: tan powder
• Vapor Pressure: 0.00513mmHg at 25°C
• Melting Point: 290-295 °C(lit.)
• Refractive Index: 1,423-1,425
• Boiling Point: 263.6 °C at 760 mmHg
• PKA: 6.54±0.11(Predicted)
• Flash Point: 113.2 °C
• PSA: 40.46000
• Density: 1.44 g/cm³
• LogP: -0.21630
• Storage Temp.: Store below +30°C.
• Solubility.: 18.43g/l
• 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

3,4,5-Trifluorophenylboronic acid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N,Xn,Xi
• Hazard Codes: N-Xn,Xi
• Statements: 51/53-36-22-36/37/38
• Safety Statements: 61-26-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=C(C(=C1)F)F)F)(O)O
• Uses: Reactant involved in: ??Preparation of phenylboronic catechol esters and determination of Lewis acidity ??Synthesis of benzopyranone derivatives as GABAA receptor modulators ??Synthesis of multisubstituted olefins and conjugate dienes ??Suzuki cross-coupling reactions ??Preparation of fluorinated aromatic poly(ether-amide)s suzuki reaction Reactant involved in:Preparation of phenylboronic catechol esters and determination of Lewis aciditySynthesis of benzopyranone derivatives as GABAA receptor modulatorsSynthesis of multisubstituted olefins and conjugate dienesSuzuki cross-coupling reactionsPreparation of fluorinated aromatic poly(ether-amide)s Intermediates of Liquid Crystals

Technology Process of 3,4,5-Trifluorophenylboronic acid

There total 10 articles about 3,4,5-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: 82.0%

Trimethyl borate (121-43-7,63156-11-6) + 3,4,5-trifluoro-1-bromobenzene (138526-69-9) → 3,4,5-trifluorophenylboronic acid (143418-49-9)

Guidance literature:

3,4,5-trifluoro-1-bromobenzene; With magnesium; ethylene dibromide; In tetrahydrofuran; at 5 - 20 ℃; for 2h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; at -30 - -27 ℃;

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 4h; Temperature;

Reference yield: 82.0%

Trimethyl borate (121-43-7,63156-11-6) + 3,4,5-trifluorophenylmagnesium bromide (156006-28-9) + 3,4,5-trifluoro-1-bromobenzene (138526-69-9) → 3,4,5-trifluorophenylboronic acid (143418-49-9)

Guidance literature:

3,4,5-trifluorophenylmagnesium bromide; 3,4,5-trifluoro-1-bromobenzene; With magnesium; In tetrahydrofuran; at 5 - 15 ℃; for 3h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; at -20 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; at -20 - 25 ℃; for 15h; Temperature; Inert atmosphere;

DOI:10.1021/acs.oprd.9b00208

Reference yield: 80.1%

hydrogenchloride (7647-01-0,15364-23-5) + Triisopropyl borate (5419-55-6) + 3,4,5-trifluoro-1-bromobenzene (138526-69-9) → 3,4,5-trifluorophenylboronic acid (143418-49-9)

Guidance literature:

5-bromo-1,2,3-trifluorobenzene; With iodine; magnesium; In 2-methyltetrahydrofuran; at 40 - 50 ℃;

Triisopropyl borate; In 2-methyltetrahydrofuran; at 15 - 25 ℃; for 4h;

hydrogenchloride; In 2-methyltetrahydrofuran; water monomer; for 0.5h; Temperature; Solvent;

upstream raw materials:

Triisopropyl borate

3,4,5-trifluoro-1-bromobenzene

Trimethyl borate

tris(3,4,5-trifluorophenyl)boroxine

Downstream raw materials:

1,2,3-trifluorobenzene

tris(3,4,5-trifluorophenyl)boroxine

C₄₄H₄₃F₆NO₂

Refernces

• 1、 -. "Preparation method of 3, 4, 5-trifluorophenylboronic acid". Paragraph 0028-0039. . Retrieved 2022/04/06.
• 2、 -. "Application method of Grignard reaction". Paragraph 0040-0049. . Retrieved 2021/03/31.