827614-70-0

Basic information

• Product Name: 3,4,5-TRIFLUOROPHENYLBORONIC ACID, PINACOL ESTER
• Synonyms: 3,4,5-TRIFLUOROPHENYLBORONIC ACID, PINACOL ESTER;2-(3,4,5-TRIFLUOROBENZENE)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-(3,4,5-TRIFLUOROPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-(3,4,5-Trifluorophenyl)-4,4,5,5-tetramethyl-;5-Trifluorophenyl)-4;3,4,5-Trifluorobenzeneboronic acid pinacol ester;4,4,5,5-TetraMethyl-2-(3,4,5-trifluorophenyl)-1,3,2-dioxaborolane;1,3,2-Dioxaborolane,4,4,5,5-tetraMethyl-2-(3,4,5-trifluorophenyl)-
• CAS NO: 827614-70-0
• Molecular Formula: C₁₂H₁₄BF₃O₂
• Molecular Weight: 258.04
• Mol File: 827614-70-0.mol

Chemical Properties

• Boiling Point: 285 °C at 760 mmHg
• Flash Point: 126.2 °C
• Appearance: /
• Density: 1.17 g/cm³
• Vapor Pressure: 0.00494mmHg at 25°C
• Refractive Index: 1.4520 to 1.4560
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,4,5-TRIFLUOROPHENYLBORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-TRIFLUOROPHENYLBORONIC ACID, PINACOL ESTER(827614-70-0)
• EPA Substance Registry System: 3,4,5-TRIFLUOROPHENYLBORONIC ACID, PINACOL ESTER(827614-70-0)

Safety Data

• Hazardous Substances Data: 827614-70-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
3,4,5-Trifluorophenylboronic Acid, Pinacol Ester is used as a reagent for Suzuki coupling reactions, a widely employed method in the synthesis of biaryl compounds. Its application in this process is due to its ability to form stable intermediates, which are crucial for the success of the reaction.
Used in Research and Development Laboratories:
3,4,5-Trifluorophenylboronic Acid, Pinacol Ester is used as a research compound for the development of new synthetic methods and the exploration of its potential applications in various chemical processes. Its stability and reactivity make it a valuable tool for scientists working in the field of organic chemistry.
Used in Pharmaceutical Industry:
3,4,5-Trifluorophenylboronic Acid, Pinacol Ester is used as a building block in the synthesis of complex organic molecules, including potential drug candidates. Its versatility in forming biaryl compounds makes it a valuable asset in the development of new pharmaceuticals with improved properties and therapeutic effects.
Used in Material Science:
3,4,5-Trifluorophenylboronic Acid, Pinacol Ester is used as a precursor in the synthesis of advanced materials, such as polymers and composites, with tailored properties for specific applications. Its ability to form stable intermediates in Suzuki coupling reactions allows for the creation of novel materials with improved performance characteristics.

InChI:InChI=1/C12H14BF3O2/c1-11(2)12(3,4)18-13(17-11)7-5-8(14)10(16)9(15)6-7/h5-6H,1-4H3

Upstream product

• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 138526-69-9 3,4,5-trifluoro-1-bromobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 1489-53-8 1,2,3-trifluorobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 2367-82-0 1,2,3,5-tetrafluorobenzene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1338809-70-3 C₁₂H₆BF₃O₂ 

Downstream Products

• 1146593-95-4 (3,4,5-trifluorophenyl)cycloheptane 
• 1313373-82-8 2,3,6,7-tetrakis(4-tert-butylphenyl)-9,10-bis(3,4,5-trifluorophenyl)anthracene 

Relevant articles and documents

Catalytic Boration of Alkyl Halides with Borane without Hydrodehalogenation Enabled by Titanium Catalyst

An unprecedented and general titanium-catalyzed boration of alkyl (pseudo)halides (alkyl-X, X=I, Br, Cl, OMs) with borane (HBpin, HBcat) is reported. The use of titanium catalyst can successfully suppress the undesired hydrodehalogenation products that prevail using other transition-metal catalysts. A series of synthetically useful alkyl boronate esters are readily obtained from various (primary, secondary, and tertiary) alkyl electrophiles, including unactivated alkyl chlorides, with tolerance of other reducing functional groups such as ester, alkene, and carbamate. Preliminary studies on the mechanism revealed a possible radical reaction pathway. Further extension of our strategy to aryl bromides is also demonstrated.

Energy level tuning of ‘Z'-shaped small molecular non-fullerene electron acceptors based on a dipyrrolo[2,3-b:2′,3′-e]pyrazine-2,6(1H,5H)-dione acceptor unit for organic photovoltaic applications: a joint experimental and DFT investigation on the effect o

Three different fluorine (4-CF3, 3,5-CF3 and 3,4,5-F) end-capped, A2-π-A1-π-A2 type small molecular non-fullerene acceptor molecules (1CFPzDP, 2CFPzDP, and 3FPzDP) containing a common central core acc

Selective Photocatalytic C-F Borylation of Polyfluoroarenes by Rh/Ni Dual Catalysis Providing Valuable Fluorinated Arylboronate Esters

A highly selective and general photocatalytic C-F borylation protocol that employs a rhodium biphenyl complex as a triplet sensitizer and the nickel catalyst [Ni(IMes)2] (IMes = 1,3-dimesitylimidazoline-2-ylidene) for the C-F bond activation and defluoroborylation process is reported. This tandem catalyst system operates with visible (blue, 400 nm) light and achieves borylation of a wide range of fluoroarenes with B2pin2 at room temperature in excellent yields and with high selectivity. Direct irradiation of the intermediary C-F bond oxidative addition product trans-[NiF(ArF)(IMes)2] leads to very fast decomposition when B2pin2 is present. This destructive pathway can be bypassed by indirect excitation of the triplet states of the nickel(II) complex via the photoexcited rhodium biphenyl complex. Mechanistic studies suggest that the exceptionally long-lived triplet excited state of the Rh biphenyl complex used as the photosensitizer allows for efficient triplet energy transfer to trans-[NiF(ArF)(IMes)2], which leads to dissociation of one of the NHC ligands. This contrasts with the majority of current photocatalytic transformations, which employ transition metals as excited state single electron transfer agents. We have previously reported that C(arene)-F bond activation with [Ni(IMes)2] is facile at room temperature, but that the transmetalation step with B2pin2 is associated with a high energy barrier. Thus, this triplet energy transfer ultimately leads to a greatly enhanced rate constant for the transmetalation step and thus for the whole borylation process. While addition of a fluoride source such as CsF enhances the yield, it is not absolutely required. We attribute this yield-enhancing effect to (i) formation of an anionic adduct of B2pin2, i.e., FB2pin2-, as an efficient, much more nucleophilic {Bpin-} transfer reagent for the borylation/transmetalation process, and/or (ii) trapping of the Lewis acidic side product FBpin by formation of [F2Bpin]- to avoid the formation of a significant amount of NHC-FBpin and consequently decomposition of {Ni(NHC)2} species in the reaction mixture.

Cobalt-Catalyzed Regioselective Borylation of Arenes: N-Heterocyclic Silylene as an Electron Donor in the Metal-Mediated Activation of C?H Bonds

C?H Borylation of arenes has been a subject of great interest recently because of its atom-economy and the wide applicability of borylated products in value-added synthesis. A new bis(silylene)cobalt(II) complex bearing a bis(N-heterocyclic silylene)-pyridine pincer ligand (SiNSi) has been synthesized and structurally characterized. It enabled the regioselective catalytic C?H borylation of pyridines, furans, and fluorinated arenes. Notably, it exhibited complementary regioselectivity for the borylation of fluorinated arenes compared to previously known catalytic systems, demonstrating that N-heterocyclic silylene donors have enormous potential in metal-catalyzed catalytic applications.

Preparing (Multi)Fluoroarenes as Building Blocks for Synthesis: Nickel-Catalyzed Borylation of Polyfluoroarenes via C-F Bond Cleavage

The [Ni(IMes)2]-catalyzed transformation of fluoroarenes into arylboronic acid pinacol esters via C-F bond activation and transmetalation with bis(pinacolato)diboron (B2pin2) is reported. Various partially fluorinated arenes with different degrees of fluorination were converted into their corresponding boronate esters.

Investigation of a lithium-halogen exchange flow process for the preparation of boronates by using a cryo-flow reactor

Conducting low-temperature organometallic reactions under continuous flow conditions offers the potential to more accurately control exotherms and thus provide more reproducible and scalable processes. Herein, progress towards this goal with regards to the lithium-halogen exchange/borylation reaction is reported. In addition to improving the scope of substrates available on a research scale, methods to improve reaction profiles and expedite purification of the products are also described. On moving to a continuous system, thermocouple measurements have been used to track exotherms and provide a level of safety for continuous processing of organometallic reagents. The use of an in-line continuous liquid-liquid separation device to circumvent labour intensive downstream off-line processing is also reported. A cool setup: A small footprint, modular setup based around a cryo-flow reactor is reported for the preparation of gram quantities of boronic esters. With minimum alteration, including the addition of a data logger with thermocouples and a liquid-liquid separator, the same equipment can be used to scale the process, inclusive of an in-line extraction. Copyright

Syntheses of (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)arenes through Pd-catalyzed borylation of arylbromides with the successive use of 2,2′-bis(1,3,2-benzodioxaborole) and pinacol

Syntheses of (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)arenes through the Pd-catalyzed borylation of arylbromides with the successive use of 2,2′-bis(1,3,2-benzodioxaborole) and pinacol were investigated. PdCl 2(dppf) and AcOK in EtOH or DMSO successfully provided (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)arenes. In particular, this method was more effective in the borylation of arylbromides bearing sulfonyl groups than the conventional Pd-catalyzed borylation using pinacolborane or bis(pinacolato)diboron.