214360-65-3

Basic information

• Product Name: 4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER
• Synonyms: 4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER;4,4,5,5-TETRAMETHYL-2-(4-TRIFLUOROMETHYLPHENYL)-1,3,2-DIOXABOROLANE;2-(4-(trifluoroMethyl)phenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-[4-(trifluoromethyl)phenyl]-1,3,2-dioxaborolane (This product is only available in Japan.)
• CAS NO: 214360-65-3
• Molecular Formula: C₁₃H₁₆BF₃O₂
• Molecular Weight: 272.07
• Mol File: 214360-65-3.mol
• Article Data: 122

Chemical Properties

• Melting Point: 68-69 °C
• Boiling Point: 291.4 °C at 760 mmHg
• Flash Point: 130 °C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 0.00159mmHg at 25°C
• Refractive Index: 1.469
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER(214360-65-3)
• EPA Substance Registry System: 4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER(214360-65-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 214360-65-3(Hazardous Substances Data)

Usage

General Description

The chemical "4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER" is a boronic acid derivative that contains a trifluoromethylphenyl group. It is commonly used as a reagent in organic synthesis, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. 4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is often utilized in the Suzuki-Miyaura cross-coupling reaction, where it acts as a nucleophile to form new carbon-carbon bonds. The pinacol ester group serves to protect the boronic acid functionality, making it more stable and easier to handle in reactions. Overall, "4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER" is a valuable building block in organic chemistry for the construction of various pharmaceuticals, agrochemicals, and materials.

InChI:InChI=1/C14H16BF3O3/c1-13(2)14(3,4)21-15(20-13)9-5-7-10(8-6-9)19-12(18)11(16)17/h5-8H,1-4H3

Upstream product

• 98-08-8 α,α,α-trifluorotoluene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 51901-85-0 bromocatecholborane 
• 7440-66-6 zinc 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 98-56-6 4-chlorobenzotrifluoride 
• 368-94-5 4-trifluoromethyl-benzoyl fluoride 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 455-13-0 4-Iodobenzotrifluoride 
• 2923-56-0 4-(trifluoromethyl)phenylhydrazine hydrochloride 

Downstream Products

• 1187791-58-7 2-(4-trifluoromethylphenyl)cyclopent-2-enone 
• 1185842-26-5 N-[(4-trifluoromethylphenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]acetamide 
• 1185842-28-7 N-[(4-trifluoromethylphenyl)(phenyl)methyl]acetamide 
• 402-44-8 4-Fluorobenzotrifluoride 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 16307-14-5 2-(4-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-1-one 
• 77918-46-8 diethyl (4-(trifluoromethyl)phenyl)-phosphonate 
• 419543-02-5 cyclohexyl-(4-trifluoromethylphenyl)-methanone 
• 5586-13-0 1-azido-4-(trifluoromethyl)benzene 
• 34913-29-6 4,4′-bis(trifluoromethyl)azobenzene 
• 1160172-06-4 1-methyl-2-phenyl-3-(4-(trifluoromethyl)phenyl)-1H-indole 
• 725229-27-6 tert-butyl 4-(4-(trifluoromethyl)benzoyl)piperidine-1-carboxylate 

Relevant articles and documents

Conclusive Evidence on the Mechanism of the Rhodium-Mediated Decyanative Borylation

The stoichiometric reactions proposed in the mechanism of the rhodium-mediated decyanative borylation have been performed and all relevant intermediates isolated and characterized including their X-ray structures. Complex RhCl{xant(PiPr2)2} (1, xant(PiPr2)2 = 9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene) reacts with bis(pinacolato)diboron (B2pin2), in benzene, to give the rhodium(III) derivative RhHCl(Bpin){xant(PiPr2)2} (4) and PhBpin. The reaction involves the oxidative addition of B2pin2 to 1 to give RhCl(Bpin)2{xant(PiPr2)2}, which eliminates ClBpin generating Rh(Bpin){xant(PiPr2)2} (2). The reaction of the latter with the solvent yields PhBpin and the monohydride RhH{xant(PiPr2)2} (6), which adds the eliminated ClBpin. Complex 4 and its catecholboryl counterpart RhHCl(Bcat){xant(PiPr2)2} (7) have also been obtained by oxidative addition of HBR2 to 1. Complex 2 is the promoter of the decyanative borylation. Thus, benzonitrile and 4-(trifluoromethyl)benzonitrile insert into the Rh-B bond of 2 to form Rh{C(R-C6H4)-NBpin}{xant(PiPr2)2} (R = H (8), p-CF3 (9)), which evolve into the aryl derivatives RhPh{xant(PiPr2)2} (3) and Rh(p-CF3-C6H4){xant(PiPr2)2} (10), as a result of the extrusion of CNBpin. The reactions of 3 and 10 with B2pin2 yield the arylBpin products and regenerate 2.

Cu-mediated: vs. Cu-free selective borylation of aryl alkyl sulfones

A Cu-catalysed borylation of aryl alkyl sulfones was developed for the high yield synthesis of versatile arylboronic esters using a readily prepared NHC-Cu catalyst. In addition, the selective cleavage of either alkyl(C)-sulfonyl or aryl(C)-sulfonyl bonds

Photochemical and electrochemical C-N borylation of arylhydrazines

The C-N borylation of arylhydrazine hydrochlorides with bis(pinacolato)diboron was achieved under photochemical and electrochemical conditions, respectively. This novel and scalable transformation provides two efficient and mild transition-metal-free synt