2-(Trifluoromethyl)phenylboronic acid

Base Information

• Chemical Name: 2-(Trifluoromethyl)phenylboronic acid
• CAS No.: 1423-27-4
• Molecular Formula: C7H6BF3O2
• Molecular Weight: 189.93
• Hs Code.: 29163990
• European Community (EC) Number: 640-203-7
• DSSTox Substance ID: DTXSID60370276
• Nikkaji Number: J1.040.313H
• Wikidata: Q72512319
• ChEMBL ID: CHEMBL349181
• Mol file: 1423-27-4.mol

Synonyms:1423-27-4;2-(Trifluoromethyl)phenylboronic acid;2-Trifluoromethylphenylboronic acid;(2-Trifluoromethyl)phenylboronic acid;[2-(trifluoromethyl)phenyl]boronic Acid;(2-(trifluoromethyl)phenyl)boronic acid;2-(Trifluoromethyl)benzeneboronic acid;MFCD00236059;2-trifluoromethyl phenylboronic acid;[2-(Trifluoromethyl)Phenyl]Boranediol;Boronic acid, [2-(trifluoromethyl)phenyl]-;o-trifluoromethylphenylboronic acid;2-(trifluoromethyl)phenylboronicacid;SCHEMBL4288;alpha,alpha,alpha-Trifluoro-o-tolueneboronic Acid;CHEMBL349181;BDBM26136;2-trifluromethylphenylboronic acid;DTXSID60370276;2-trifluoromethyl-phenylboronic acid;2-trifluoromethylbenzeneboronic acid;2-trifluoromethylphenyl boronic acid;BCP26907;(2-Trifluoromethyl)phenylboronicacid;0-TRUFLUOROMETHYLBORONIC ACID;2-(trifluoromethy)phenylboronic acid;2-(trifluromethyl)phenylboronic acid;(2-trifluoromethylphenyl)boronic acid;2-trifluoromethyl phenyl boronic acid;2-trifluoromethyl-phenyl boronic acid;2-trifluoromethyl-phenyl-boronic acid;2-trifluoromethylbenzene boronic acid;(2-trifluoromethylphenyl) boronic acid;2-(tri-fluoromethyl)phenylboronic acid;2-(trifluoro-methyl)phenylboronic acid;2-(trifluoromethyl)phenyl boronic acid;2-(trifluoromethyl)phenyl-boronic acid;2-trifluoromethyl-benzene boronic acid;AKOS003585299;AB05355;AC-5352;CS-W015924;GS-6728;(2-trifluoromethyl-phenyl)-boronic acid;2-(trifluoromethyl)-benzeneboronic acid;2-(trifluoromethyl)-phenyl boronic acid;2-(trifluoromethyl)benzene boronic acid;NCGC00249479-01;NCGC00249479-02;[2-(trifluoromethyl)-phenyl]boronic acid;[2-(trifluoromethyl)phenyl]-boronic acid;SY007882;AM20060162;FT-0601797;T1800;alpha,alpha,alpha-Trifluoro-o-tolylboronic Acid;Boronic acid, B-[2-(trifluoromethyl)phenyl]-;EN300-120182;2-(Trifluoromethyl)phenylboronic acid, >=95.0%;J-510357;Z382786174

Chemical Property of 2-(Trifluoromethyl)phenylboronic acid

Chemical Property:

• Appearance/Colour: white to light beige crystalline powder
• Melting Point: 111-114 °C
• Boiling Point: 274.5 °C at 760 mmHg
• PKA: 8.11±0.58(Predicted)
• Flash Point: 119.8 °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

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1C(F)(F)F)(O)O
• Uses: suzuki reaction 2-Trifluoromethylphenylboronic Acid is a reagent in the preparation of potent inhibitors of human uric acid transporter 1 (hURAT1). 2-(Trifluoromethyl)phenylboronic acid can be used as a reactant: In Suzuki-coupling reactions to prepare 2-trifluoromethyl aryl or heteroaryl derivatives. To synthesize 4-(2-trifluoromethyl)phenylpyrrolo[2,3-d]pyrimidine as a potential antagonist of corticotropin-releasing hormone. To prepare 2-nitro-6-(trifluoromethyl)phenylboronic acid by nitration reaction.

Technology Process of 2-(Trifluoromethyl)phenylboronic acid

There total 7 articles about 2-(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: 52.0%

chloro-bis(dimethylamino)borane (6562-41-0) + water (7732-18-5) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 2-(trifluoromethyl)phenylboronic acid (1423-27-4)

Guidance literature:

chloro-bis(dimethylamino)borane; 1-chloro-2-(trifluoromethyl)benzene; With iodine; magnesium; In tetrahydrofuran; at 20 - 30 ℃; for 2.5h;

water; With ammonium chloride; In tetrahydrofuran; at 0 ℃; for 1h;

Reference yield:

Trimethyl borate (121-43-7,63156-11-6) + o-trifluoromethylphenyl bromide (392-83-6) → 2-(trifluoromethyl)phenylboronic acid (1423-27-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.bmcl.2017.03.041

Reference yield:

o-trifluoromethylphenyl bromide (392-83-6) → 2-(trifluoromethyl)phenylboronic acid (1423-27-4)

Guidance literature:

With tetrahydroxydiboron; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine; In ethanol; at 20 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1021/jo401104y

upstream raw materials:

o-trifluoromethylphenyl bromide

Triisopropyl borate

Trimethyl borate

chloro-bis(dimethylamino)borane

Downstream raw materials:

4-Chloro-2-methyl-5-nitro-6-(2-(trifluoromethyl)phenyl)-pyrimidine

(E)-3-(2-methylphenyl)acrylic acid

1-nitro-2-(2-nitrophenyl)benzene

2-nitro-2'-(trifluoromethyl)-1,1'-biphenyl

Refernces

• 1、 Yang, Xintuo,Pang, Xuehai,Fan, Lei,Li, Xinghai,Chen, Yuanwei. "Synthesis and evaluation of sulfonamide derivatives as potent Human Uric Acid Transporter 1 (hURAT1) inhibitors". supporting information. p. 1919 - 1922. Retrieved 2017/04/10.
• 2、 Molander, Gary A.,Cavalcanti, Livia N.,Garcia-Garcia, Carolina. "Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4]". . p. 6427 - 6439. Retrieved 2013/07/26.