179113-90-7

Usage

Uses

Used in Suzuki Reaction:
3-Trifluoromethoxyphenylboronic acid is used as a reagent in the Suzuki reaction, a widely employed cross-coupling reaction in organic chemistry for the formation of carbon-carbon bonds.
Used in Pharmaceutical Industry:
3-Trifluoromethoxyphenylboronic acid is used as a precursor in the synthesis of various biologically active compounds, including:
1. Multisubstituted purines as P2X7 antagonists for the treatment of pain.
2. Heteroaryl substituted tetrahydropyrroloijquinolinone derivatives as aldosterone synthase inhibitors.
3. Fluorohydroquinolineethanol as a CETP inhibitor.
4. Biaryl amides with muscarinic acetylcholine receptor subtype M1 agonist activity.
5. C2-aryl pyrrolobenzodiazepine antitumor agents.
6. Piperazine-bisamide for obesity treatments.
Additionally, 3-(Trifluoromethyloxy)phenylboronic acid is used as a reagent in the preparation of pyrrolo[1,2-a]pyrazinones, which act as inhibitors of PIM kinases, playing a significant role in the development of targeted cancer therapies.

InChI:InChI=1/C7H6BF3O3/c9-7(10,11)14-6-3-1-2-5(4-6)8(12)13/h1-4,12-13H

Upstream product

• 2252-44-0 1-bromo-3-(trifluoromethoxy)benzene 
• 13675-18-8 tetrahydroxydiboron 

Downstream Products

• 306935-96-6 5-(3-trifluoromethoxy-phenyl)-furan-2-carbaldehyde 
• 604805-11-0 3-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-3-hydroxy-1-(3-trifluoromethoxy-phenyl)-1,3-dihydro-indol-2-one 
• 954223-82-6 C₁₁H₆ClF₃N₂O 
• 588731-48-0 6-[(6-chloro-pyridin-3-yl)-(3-methyl-3H-imidazol-4-yl)-methoxymethyl]-3'-trifluoromethoxy-biphenyl-3-carbonitrile 
• 702689-96-1 (S,S)-6-(4-amino-butyl)-1-biphenyl-4-ylmethyl-3-[4-(3-trifluoromethoxy-phenoxy)-benzyl]-piperazine-2,5-dione 
• 481630-67-5 1-benzyl-5-[3-(trifluoromethoxy)phenyl]-1H-indole 
• 946614-11-5 1-Trifluoromethoxy-3-(1-trifluoromethyl-vinyl)-benzene 
• 753029-05-9 C₃₄H₃₆Cl₂F₃N₃O₂ 
• 1092477-65-0 (+/-)-(4-methyl-1-piperazinyl){3-[(trifluoromethyl)oxy]phenyl}acetic acid 
• 1160268-80-3 5-(dipropylamino)-1-methyl-3-(3-(trifluoromethoxy)phenyl)-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 
• 1225338-89-5 N-[3'-(trifluoromethoxy)biphenyl-4-yl]cyclopropanesulfonamide 

Relevant academic research and scientific papers

Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts

We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly to boronic acids. This borylation method has a broad scope and functional group tolerance. We show that it can be further extended to boronic esters and carried out on gram scale as well as under flow conditions.

Highly efficient one-pot access to functionalized arylboronic acids via noncryogenic bromine/magnesium exchanges

A general and convenient protocol for the electrophilic borylation of aryl Grignard reagents prepared from arylbromides by direct insertion of magnesium in the presence of LiCl or by Mg/Br exchange with iPrMgCl?LiCl has been developed. Various aryl boronic acids were synthesized in a straightforward manner in excellent yields at 0 °C.

2-, 3-, and 4-(Trifluoromethoxy)phenyllithiums: Versatile intermediates offering access to a variety of new organofluorine compounds

Consecutive treatment of (trifluoromethoxy)benzene with sec-butyllithium and electrophilic reagents affords previously inaccessible ortho-substituted derivatives in generally excellent yields. 2-(Trifluoromethoxy)phenyllithium acts as the key intermediate. The 3- and 4-isomers can readily be generated from the corresponding 3- and 4-bromo precursors by halogen-metal interconversion with butyllithium or tertbutyllithium. Upon trapping of the 2-, 3- and 4-(trifluoromethoxy)phenyllithiums with 11 different electrophiles the expected products were formed in generally high yields. Only the attempted nucleophilic addition of 2-(trifluoromethoxy)phenyllithium to oxirane did not succeed. This failure is tentatively attributed to a lowering of the nucleophilicity by fluorine-lithium interactions. Conformationally restricted analogs - i.e., 2,2-difluoro-1,3-benzodioxol-4-phenyllithium and its 5-fluoro- and 5-bromo-substituted congeners - did indeed react smoothly with oxirane, affording the adducts in ordinary yields.