(2,6-Bis(trifluoromethyl)phenyl)boronic acid

Base Information

• Chemical Name: (2,6-Bis(trifluoromethyl)phenyl)boronic acid
• CAS No.: 681812-07-7
• Molecular Formula: C8H5BF6O2
• Molecular Weight: 257.928
• Hs Code.: 2931900090
• European Community (EC) Number: 640-512-7
• DSSTox Substance ID: DTXSID10382526
• Nikkaji Number: J2.587.054I
• Wikidata: Q82173887
• Mol file: 681812-07-7.mol

Synonyms:681812-07-7;2,6-Bis(trifluoromethyl)phenylboronic acid;(2,6-Bis(trifluoromethyl)phenyl)boronic acid;2,6-Bis(trifluoromethyl)benzeneboronic acid;[2,6-bis(trifluoromethyl)phenyl]boronic Acid;MFCD04039321;Boronic acid, [2,6-bis(trifluoromethyl)phenyl]-;SCHEMBL3783762;DTXSID10382526;WAMPGNNEOZGBHR-UHFFFAOYSA-N;AC1052;AKOS005254947;AB17340;PS-9476;2,6-Bis(trifluoromethyl)phenylboronicacid;SY023642;CS-0173975;FT-0698823;A867108;2,6-Bis(trifluoromethyl)benzeneboronic acid, AldrichCPR;(R)-2-BENZYL-SUCCINICACID1-BENZYLESTER4-TERT-BUTYLESTER

Chemical Property of (2,6-Bis(trifluoromethyl)phenyl)boronic acid

Chemical Property:

• Vapor Pressure: 0.00708mmHg at 25°C
• Melting Point: 168-171
• Refractive Index: 1.419
• Boiling Point: 258.3°C at 760 mmHg
• PKA: 7.69±0.58(Predicted)
• Flash Point: 110°C
• PSA: 40.46000
• Density: 1.5g/cm³
• LogP: 1.40400
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 258.0286785
• Heavy Atom Count: 17
• Complexity: 242

Purity/Quality:

97% ^*data from raw suppliers

(2,6-Bis(trifluoromethyl)phenyl)boronicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=CC=C1C(F)(F)F)C(F)(F)F)(O)O
• Uses: 2,6-Bis(trifluoromethyl)benzeneboronic acid is used as pharmaceutical intermediate.

Technology Process of (2,6-Bis(trifluoromethyl)phenyl)boronic acid

There total 9 articles about (2,6-Bis(trifluoromethyl)phenyl)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: 74.0%

(2,6-bis(trifluoromethyl)phenyl)trifluoro-λ4-borane potassium salt + water (7732-18-5) → (2,6-bis-trifluoromethyl-phenyl)-boronic acid (681812-07-7)

Guidance literature:

With chloro-trimethyl-silane; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/acs.orglett.8b02427

Reference yield: 52.0%

Trimethyl borate (121-43-7,63156-11-6) + 1,3-bis(trifluoromethyl)benzene (402-31-3) + water (7732-18-5) → 2,4-bis(trifluoromethyl)phenylboronic acid (153254-09-2) + (2,6-bis-trifluoromethyl-phenyl)-boronic acid (681812-07-7)

Guidance literature:

1,3-bis(trifluoromethyl)benzene; With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; hexane; at -78 ℃; for 3h;

Trimethyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1h;

water; With hydrogenchloride; In tetrahydrofuran; hexane; at 20 ℃; for 12h;

DOI:10.1021/acs.orglett.8b02427

Reference yield:

3-(2-(2,6-bis(trifluoromethyl)phenyl)-1,3,2-dioxaborinan-4-yl)propyl acetate → (2,6-bis-trifluoromethyl-phenyl)-boronic acid (681812-07-7)

Guidance literature:

Multi-step reaction with 4 steps

1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 °C

2: silver(l) oxide / 1,2-dichloro-ethane / Reflux

3: methanol / water / 2 h / 20 °C

4: chloro-trimethyl-silane / acetonitrile / 1 h / 20 °C

With methanol; chloro-trimethyl-silane; diisobutylaluminium hydride; silver(l) oxide; In hexane; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/acs.orglett.8b02427

upstream raw materials:

2,6-(CF₃)2C₆H₃BCl₂

1,3-bis(trifluoromethyl)benzene

Trimethyl borate

water

Downstream raw materials:

C₂₃H₂₀F₆N₂

1,3-bis(trifluoromethyl)benzene