3-(Trifluoromethoxy)phenylboronic acid

Base Information

• Chemical Name: 3-(Trifluoromethoxy)phenylboronic acid
• CAS No.: 179113-90-7
• Molecular Formula: C7H6BF3O3
• Molecular Weight: 205.929
• Hs Code.: 29163990
• European Community (EC) Number: 642-464-2
• DSSTox Substance ID: DTXSID40370274
• Nikkaji Number: J1.490.426C
• Wikidata: Q72511491
• Mol file: 179113-90-7.mol

Synonyms:179113-90-7;3-(Trifluoromethoxy)phenylboronic acid;3-Trifluoromethoxyphenylboronic acid;(3-(Trifluoromethoxy)phenyl)boronic acid;3-(Trifluoromethoxy)benzeneboronic Acid;[3-(trifluoromethoxy)phenyl]boronic Acid;MFCD01320697;3-(trifluoromethoxy)phenyl boronic acid;Boronic acid, [3-(trifluoromethoxy)phenyl]-;3-(trifluoromethyloxy)phenylboronic acid;m-(trifluoromethoxy)phenylboronic acid;Boronic acid, B-[3-(trifluoromethoxy)phenyl]-;SCHEMBL28261;DTXSID40370274;BCP21459;3-trifluoromethoxybenzeneboronic acid;3-trifluoromethoxy-phenylboronic acid;3-trifluoromethoxyphenyl boronic acid;BBL104380;STL558637;3-Trifluoromethoxy-benzeneboronic acid;3-trifluoromethoxybenzene boronic acid;3-trifluoromethoxylphenyl boronic acid;3-(Trifluoromethoxy)phenylboranic acid;3-trifluoromethoxy-phenyl boronic acid;AKOS004116215;AB09003;AC-5362;CS-W015357;PS-9533;3-(trifluoromethoxy) phenylboronic acid;3-(trifluoromethoxy)-phenylboronic acid;NCGC00249558-01;BP-20269;SY014636;(3-(trifluoro methoxy)phenyl)boronic acid;A3975;AM20060165;FT-0613901;T2362;{3-[(trifluoromethyl)oxy]phenyl}boronic acid;EN300-225310;J-513118;Z1037570248

Chemical Property of 3-(Trifluoromethoxy)phenylboronic acid

Chemical Property:

• Appearance/Colour: almost white to slightly beige powder and chunk
• Vapor Pressure: 0.00425mmHg at 25°C
• Melting Point: 84-89 °C(lit.)
• Refractive Index: 1.461
• Boiling Point: 266.6 °C at 760 mmHg
• PKA: 7.39±0.10(Predicted)
• Flash Point: 115.1 °C
• PSA: 49.69000
• Density: 1.41 g/cm³
• LogP: 0.26500
• Storage Temp.: 0-6°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 206.0362087
• Heavy Atom Count: 14
• Complexity: 186

Purity/Quality:

99% ^*data from raw suppliers

3-Trifluoromethoxyphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC=C1)OC(F)(F)F)(O)O
• Uses: suzuki reaction 3-(Trifluoromethyloxy)phenylboronic Acid is used as a reagent in the preparation of pyrrolo[1,2-a]pyrazinones as inhibitors of PIM kinases. Precursor commonly used in the synthesis of biologically active compounds including:Multisubstituted purines for use as P2X7 antagonists in the treatment of painHeteroaryl substituted tetrahydropyrroloijquinolinone derivatives as aldosterone synthase inhibitorsFluorohydroquinolineethanol as a CETP inhibitorBiaryl amides with muscarinic acetylcholine receptor subtype M1 agonist activityC2-aryl pyrrolobenzodiasepine antitumor agentsPiperazine-bisamide for obesity treatments

Technology Process of 3-(Trifluoromethoxy)phenylboronic acid

There total 2 articles about 3-(Trifluoromethoxy)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: 85.0%

1-bromo-3-(trifluoromethoxy)benzene (2252-44-0) → (3-(trifluoromethoxy)phenyl)boronic acid (179113-90-7)

Guidance literature:

1-bromo-3-(trifluoromethoxy)benzene; With diisobutylaluminium hydride; magnesium; lithium chloride; In tetrahydrofuran; toluene; at 20 ℃; for 15h; Inert atmosphere;

With Trimethyl borate; In tetrahydrofuran; toluene; at 0 ℃; Inert atmosphere;

With hydrogenchloride; water; In tetrahydrofuran; toluene; at 0 ℃; Inert atmosphere;

DOI:10.1021/ol2016252

Reference yield: 82.0%

tetrahydroxydiboron (13675-18-8) + 1-bromo-3-(trifluoromethoxy)benzene (2252-44-0) → (3-(trifluoromethoxy)phenyl)boronic acid (179113-90-7)

Guidance literature:

In methanol; at 15 ℃; for 3h; Microwave irradiation;

DOI:10.1021/jacs.6b01376

Reference yield: 94.0%

2,4-diamino-5-iodo-6-(3-methoxypropoxy)pyrimidine + (3-(trifluoromethoxy)phenyl)boronic acid (179113-90-7) → 2,4-diamino-5-(3-(trifluoromethoxy)phenyl)-6-(3-methoxypropoxy)pyrimidine

Guidance literature:

With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate; In ethanol; water; toluene; at 90 ℃; for 24h; Inert atmosphere;

DOI:10.3390/molecules22101592

upstream raw materials:

1-bromo-3-(trifluoromethoxy)benzene

tetrahydroxydiboron

Downstream raw materials:

1,6-dimethyl-2-oxo-5-(3-(trifluoromethoxy)phenyl)-1,2-dihydro-3-pyridinecarbonitrile

5-(3-trifluoromethoxy-phenyl)-furan-2-carbaldehyde

3-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-3-hydroxy-1-(3-trifluoromethoxy-phenyl)-1,3-dihydro-indol-2-one

Refernces

• 1、 Leermann, Timo,Leroux, Frederic R.,Colobert, Francoise. "Highly efficient one-pot access to functionalized arylboronic acids via noncryogenic bromine/magnesium exchanges". supporting information; experimental part. p. 4479 - 4481. Retrieved 2011/10/09.