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
• Article Data: 7

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

General Description

3,4,5-Trifluorophenylboronic Acid, Pinacol Ester is a chemical compound that belongs to the category of organoboronic acids and esters. It is commonly used in the field of organic chemistry, particularly in Suzuki coupling reactions. This pale yellow or off-white solid is temperature-sensitive and may pose a health hazard if handled improperly. It's highly stable under normal temperatures and pressures. Due to its properties, it is often utilized in research and development laboratories. It is usually stored in cool and dry place, away from heat and incompatibles such as oxidizing agents.

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

• 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 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 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.

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.

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.