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

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

Uses

Used in Organic Synthesis:
4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds, which are crucial in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is used as a key intermediate in the synthesis of various drugs. Its ability to form new bonds makes it valuable for the development of novel pharmaceutical compounds with specific therapeutic properties.
Used in Agrochemical Industry:
4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is utilized as a building block in the creation of agrochemicals, contributing to the development of new pesticides and other agricultural chemicals that can improve crop protection and yield.
Used in Materials Science:
In the field of materials science, 4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is employed in the synthesis of advanced materials with unique properties, such as high-performance polymers and specialty materials for various applications.
Used in Suzuki-Miyaura Cross-Coupling Reaction:
4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is used as a nucleophile in the Suzuki-Miyaura cross-coupling reaction, a widely employed method for the formation of new carbon-carbon bonds, which is essential for the synthesis of a broad range of organic compounds, including those with potential applications in medicine, materials, and other industries.

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 
• 98-56-6 4-chlorobenzotrifluoride 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 455-13-0 4-Iodobenzotrifluoride 
• 51901-85-0 bromocatecholborane 
• 7440-66-6 zinc 
• 455-14-1 4-trifluoromethylphenylamine 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 132803-38-4 Benzenesulfonic acid 4-trifluoromethyl-phenyl ester 
• 345958-72-7 4-(trifluoromethyl)phenyl 4-methylbenzenesulfonate 
• 128796-39-4 4-trifluoromethylphenylboronic acid 

Downstream Products

• 1008756-39-5 C₂₀H₁₂F₆S 
• 1187791-58-7 2-(4-trifluoromethylphenyl)cyclopent-2-enone 
• 1234215-27-0 1-(hex-1-en-3-yl)-4-(trifluoromethyl)benzene 
• 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 
• 1346641-89-1 C₂₆H₁₄F₁₀N₂O 
• 1377503-02-0 (S)-2-(tertbutoxy)-2-(2-methyl-4-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-b]pyridin-3-yl)acetic acid 
• 1377503-27-9 (S)-methyl-2-(tertbutoxy)-2-(2-methyl-4-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-b]pyridin-3-yl)acetic acid 
• 1373773-66-0 2,5-bis(3’-hexyl-5’-[4-(trifluoromethyl)phenyl]thiophen-2’-yl)thiazolo-[5,4-d]thiazole 
• 402-44-8 4-Fluorobenzotrifluoride 
• 1261600-44-5 5-[4-(trifluoromethyl)phenyl]pyridine-3-carbonitrile 
• 1590397-18-4 2-[(4-fluorobenzenesulfonyl)(isopropyl)amino]-N-(5-fluoro-4'-trifluoromethylbiphenyl-3-ylmethyl)acetamide 
• 1590397-19-5 2-[(4-fluorobenzenesulfonyl)(isopropyl)amino]-N-(4-fluoro-4'-trifluoromethylbiphenyl-3-ylmethyl)-acetamide 
• 1590397-25-3 2-[(4-fluorobenzenesulfonyl)(methyl)amino]-N-(5-methoxy-4'-trifluoromethylbiphenyl-3-ylmethyl)acetamide 

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

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands

Catalysts based on the combination of Pd(OAc)2 and the electron-deficient phosphatrioxa-adamantane ligands are described for borylation of aryl bromides and chlorides. Catalytic evaluation of a small library of phosphatrioxa-adamantane ligands provided some insights on the preferred ligand steric profile for borylation reactions. The corresponding aryl boronate esters were accessed under mild conditions (25–70 °C) and isolated in high yields (up to 96%).

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

Light- and Manganese-Initiated Borylation of Aryl Diazonium Salts: Mechanistic Insight on the Ultrafast Time-Scale Revealed by Time-Resolved Spectroscopic Analysis

Manganese-mediated borylation of aryl/heteroaryl diazonium salts emerges as a general and versatile synthetic methodology for the synthesis of the corresponding boronate esters. The reaction proved an ideal testing ground for delineating the Mn species responsible for the photochemical reaction processes, that is, involving either Mn radical or Mn cationic species, which is dependent on the presence of a suitably strong oxidant. Our findings are important for a plethora of processes employing Mn-containing carbonyl species as initiators and/or catalysts, which have considerable potential in synthetic applications.

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

Compound for patterning of fluorine-containing metal or electrode and organic electronic element using the same An electronic device is provided to form a fine pattern of an electrode without using a shadow mask by using the fluorinated compound as a metal or an electrode patterning material, thereby easily manufacturing a transparent display having a high light transmittance, thereby facilitating UDC application.

Evaluation of the role of graphene-based Cu(i) catalysts in borylation reactions

Carbon-supported catalysts have been considered as macromolecular ligands which modulate the activity of the metallic catalytic center. Understanding the properties and the factors that control the interactions between the metal and support allows a fine tuning of the catalyzed processes. Although huge effort has been devoted to comprehending binding energies and charge transfer for single atom noble metals, the interaction of graphenic surfaces with cheap and versatile Cu(i) salts has been scarcely studied. A methodical experimental and theoretical analysis of different carbon-based Cu(i) materials in the context of the development of an efficient, general, scalable, and sustainable borylation reaction of aliphatic and aromatic halides has been performed. We have also examined the effect of microwave (MW) radiation in the preparation of these type of materials using sustainable graphite nanoplatelets (GNP) as a support. A detailed analysis of all the possible species in solution revealed that the catalysis is mainly due to an interesting synergetic Cu2O/graphene performance, which has been corroborated by an extensive theoretical study. We demonstrated through DFT calculations at a high level of theory that graphene enhances the reactivity of the metal in Cu2O against the halide derivative favoring a radical departure from the halogen. Moreover, this material is able to stabilize radical intermediates providing unexpected pathways not observed using homogeneous Cu(i) catalysed reactions. Finally, we proved that other common carbon-based supports like carbon black, graphene oxide and reduced graphene oxide provided poorer results in the borylation process.

Engaging Ag(0) single atoms in silver(I) salts-mediated C-B and C-S coupling under visible light irradiation

Silver(I) salts were found active in the borylation and sulfenylation of aryl iodides under visible light irradiation. The optimized borylation protocol using AgF did not need any additive, operated under very mild conditions, and well tolerated a broad scope of substrates and boron sources. Formation of Ag(0) single atoms (AgSAs) during the borylation reactions was examined using high-angle annular dark field aberration-corrected scanning transmission electron microscope (HAADF AC-STEM) and electron paramagnetic resonance (EPR). The activities of the silver(I) salts were affected by the anions and could be associated with their abilities in formation of AgSAs during the reactions. Kinetic studies showed that the deiodination rate was linearly correlated with the loading of AgSAs, and hence AgSAs were the true catalytic centers for the 1e?-reduction of the C-I moieties. The oxidation state of AgSAs kept 0 in both the resting and the working states. A “work-in-tandem” mechanism involving AgSAs as the catalytic centers and AgNPs as the light absorber to achieve the borylation of aryl iodides under visible light irradiation is proposed. The current approach not only provides an alternative system for borylation and sulfenylation of aryl iodides, but also reveals a new activity of silver(I) salts involving AgSAs under visible light irradiation.