3-(Trifluoromethyl)phenylboronic acid

Base Information

• Chemical Name: 3-(Trifluoromethyl)phenylboronic acid
• CAS No.: 1423-26-3
• Molecular Formula: C7H6BF3O2
• Molecular Weight: 189.93
• Hs Code.: 29319090
• DSSTox Substance ID: DTXSID20370277
• Nikkaji Number: J909.874G
• Wikidata: Q72512316
• ChEMBL ID: CHEMBL336239
• Mol file: 1423-26-3.mol

Synonyms:3-(Trifluoromethyl)phenylboronic acid;CRTH2 antagonist CT-133;CT-133

Chemical Property of 3-(Trifluoromethyl)phenylboronic acid

Chemical Property:

• Appearance/Colour: White to pale yellow powder
• Vapor Pressure: 0.00387mmHg at 25°C
• Melting Point: 163-166 °C
• Refractive Index: 1.461
• Boiling Point: 268.2 °C at 760 mmHg
• PKA: 7.55±0.10(Predicted)
• Flash Point: 116 °C
• PSA: 40.46000
• Density: 1.36 g/cm³
• LogP: 0.38520
• Storage Temp.: 0-6°C
• Solubility.: slightly sol. in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 190.0412941
• Heavy Atom Count: 13
• Complexity: 172

Purity/Quality:

99% ^*data from raw suppliers

3-(Trifluoromethyl)phenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC=C1)C(F)(F)F)(O)O
• Uses: suzuki reaction Reactant involved in:Suzuki-Miyaura cross-coupling reactionsAerobic oxidative cross-couplingMicrowave-assisted Petasis reactionsRhodium-catalyzed addition reactionsSyntehsis of biologically active molecules

Technology Process of 3-(Trifluoromethyl)phenylboronic acid

There total 9 articles about 3-(Trifluoromethyl)phenylboronic 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: 80.0%

3-bromo-1-trifluoromethylbenzene (401-78-5) → (meta-(trifluoromethyl)phenyl)boronic acid (1423-26-3)

Guidance literature:

3-bromo-1-trifluoromethylbenzene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1.5h; Inert atmosphere;

With Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol500314x

Reference yield: 78.0%

methanol (67-56-1) + diisopropylamine borane (55124-35-1) + 3-bromo-1-trifluoromethylbenzene (401-78-5) → (meta-(trifluoromethyl)phenyl)boronic acid (1423-26-3)

Guidance literature:

diisopropylamine borane; With magnesium; phenylmagnesium bromide; In tetrahydrofuran; at 20 ℃; for 0.166667h;

3-bromo-1-trifluoromethylbenzene; In tetrahydrofuran; at 70 ℃;

methanol; Further stages;

DOI:10.1016/j.tet.2018.11.036

Reference yield: 66.0%

3-bromo-1-trifluoromethylbenzene (401-78-5) + Trimethyl borate (121-43-7,63156-11-6) + water (7732-18-5) → (meta-(trifluoromethyl)phenyl)boronic acid (1423-26-3)

Guidance literature:

3-bromo-1-trifluoromethylbenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h; Schlenk technique; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Schlenk technique; Inert atmosphere;

water; With hydrogenchloride; In tetrahydrofuran; hexane; at 25 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1039/d0ob00484g

upstream raw materials:

3-(trifluoromethyl)phenyllithium

α,α,α-trifluorotoluene

bis(pinacol)diborane

3-bromo-1-trifluoromethylbenzene

Downstream raw materials:

3-Trifluormethyl-phenylborsaeure-bis-trimethylsilylester

3'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid

4-(3-trifluoromethylphenyl)anisole

3'-(trifluoromethyl)[1,1'-biphenyl]-4-ol

Refernces

• 1、 Furuta, Shohei,Kuninobu, Yoichiro,Mori, Toshiaki,Sekine, Kohei,Yoshigoe, Yusuke. "Synthesis, structures and photophysical properties of hexacoordinated organosilicon compounds with 2-(2-pyridyl)phenyl groups". supporting information. p. 3239 - 3242. Retrieved 2020/05/14.
• 2、 Fan, Chenrui,Wu, Qixu,Zhu, Chengfeng,Wu, Xiang,Li, Yougui,Luo, Yunfei,He, Jian-Bo. "Enantioselective Conjugate Addition of Aryl Halides and Triflates to Electron-Deficient Olefins via Nickel- And Rhodium-Catalyzed Sequential Relay Reactions". supporting information. p. 8888 - 8892. Retrieved 2019/10/14.