4,4,5,5-Tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane
• CAS No.: 325142-82-3
• Molecular Formula: C13H16BF3O2
• Molecular Weight: 272.075
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID70375257
• Nikkaji Number: J1.491.107C
• Wikidata: Q72512325
• Mol file: 325142-82-3.mol

Synonyms:325142-82-3;4,4,5,5-Tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane;3-trifluoromethylphenylboronic acid, pinacol ester;4,4,5,5-tetramethyl-2-[3-(trifluoromethyl)phenyl]-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(3-trifluoromethylphenyl)-1,3,2-dioxaborolane;3-Trifluoromethylphenylboronic acid pinacol ester;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[3-(trifluoromethyl)phenyl]-;4,4,5,5-Tetramethyl-2-(3-(trifluoromethyl)-phenyl)-1,3,2-dioxaborolane;SCHEMBL10248;DTXSID70375257;AKOS015960090;AB22744;AS-2653;CS-W000911;3-Trifluoromethylphenylboronicacidpinacolester;FT-0644420;T3707;N12008;EN300-1425748;A821307;3-Trifluoromethylphenylboronic acid, pinacol ester, AldrichCPR;1,3,2-dioxaborolane,4,4,5,5-tetramethyl-2-(3-(trifluoromethyl)phenyl)-;2-[3-(Trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-(3-trifluoromethyl-phenyl)-[1,3,2]dioxaborolane;4,4,5,5-tetramethyl-2-(3-trifluoromethyl-phenyl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(3-trifluoromethylphenyl)-[1,3,2]dioxaborolane;4,4,5,5-tetramethyl-2-(3-trifluoromethylphenyl)-1,3,2-dioxaborolane, AldrichCPR;3-(Trifluoromethyl)phenylboronic acid pinacol ester

Chemical Property of 4,4,5,5-Tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.00241mmHg at 25°C
• Melting Point: 43 °C
• Refractive Index: 1.456
• Boiling Point: 297.3 °C at 760 mmHg
• Flash Point: 133.6 °C
• PSA: 18.46000
• Density: 1.14 g/cm³
• LogP: 3.00460
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 272.1195444
• Heavy Atom Count: 19
• Complexity: 325

Purity/Quality:

98%min ^*data from raw suppliers

3-Trifluoromethylphenylboronic acid, pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC=C2)C(F)(F)F

Technology Process of 4,4,5,5-Tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

There total 39 articles about 4,4,5,5-Tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane 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: 91.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + (meta-(trifluoromethyl)phenyl)boronic acid (1423-26-3) → 4,4,5,5-tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (325142-82-3)

Guidance literature:

With sodium sulfate; In tetrahydrofuran; at 20 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1002/adsc.201300741

Reference yield: 86.0%

3-bromo-1-trifluoromethylbenzene (401-78-5) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 4,4,5,5-tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (325142-82-3)

Guidance literature:

3-bromo-1-trifluoromethylbenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at 20 ℃; for 12h; Inert atmosphere;

Reference yield: 85.0%

(E)-1-(3-(trifluoromethyl)phenyl)butan-1-one O-perfluorobenzoyl oxime + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (325142-82-3)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; 2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; palladium dichloride; In 1,2-dichloro-ethane; at 120 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.202006740

upstream raw materials:

α,α,α-trifluorotoluene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

bis(pinacol)diborane

m-trifluoromethylphenyl iodide

Downstream raw materials:

methyl (E)-2-(3-hydroxy-4-(4-methoxyphenyl)-5-oxofuran-2(5H)-ylidene)-2-(3-(trifluoromethyl)phenyl)acetate

C₁₆H₉F₃O₂

1-(6-(3-(trifluoromethyl)phenyl)pyridin-2-yl)ethanone

C₁₃H₁₃F₆NO₄S

Refernces

• 1、 Demonti, Luca,Mézailles, Nicolas,Nebra, Noel,Saffon-Merceron, Nathalie. "Cross-Coupling through Ag(I)/Ag(III) Redox Manifold". supporting information. p. 15396 - 15405. Retrieved 2021/10/12.
• 2、 Esteruelas, Miguel A.,Martínez, Antonio,Oliván, Montserrat,O?ate, Enrique. "Direct C?H Borylation of Arenes Catalyzed by Saturated Hydride-Boryl-Iridium-POP Complexes: Kinetic Analysis of the Elemental Steps". supporting information. p. 12632 - 12644. Retrieved 2020/09/09.