936618-92-7

Basic information

• Product Name: 3-Fluorophenylboronic Acid Pinacol Ester
• Synonyms: 3-Fluorophenylboronic Acid Pinacol Ester;2-(3-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 936618-92-7
• Molecular Formula: C12H18BFO3
• Molecular Weight: 240
• Mol File: 936618-92-7.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 286.6±23.0 °C(Predicted)
• Appearance: /
• Density: 1.05±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 3-Fluorophenylboronic Acid Pinacol Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluorophenylboronic Acid Pinacol Ester(936618-92-7)
• EPA Substance Registry System: 3-Fluorophenylboronic Acid Pinacol Ester(936618-92-7)

Safety Data

• Hazardous Substances Data: 936618-92-7(Hazardous Substances Data)

Usage

General Description

3-Fluorophenylboronic Acid Pinacol Ester is a chemical compound that is commonly used in organic synthesis and medicinal chemistry. It is a boronic ester derivative that contains a fluorine atom attached to a phenyl ring. 3-Fluorophenylboronic Acid Pinacol Ester is often employed as a reagent in Suzuki-Miyaura cross-coupling reactions, which are important in the formation of carbon-carbon bonds. Additionally, 3-Fluorophenylboronic Acid Pinacol Ester has been utilized in the development of pharmaceuticals and agrochemicals due to its versatile reactivity and potential biological activity. Overall, this chemical plays a crucial role in the production of various organic compounds and has significant applications in the pharmaceutical and chemical industries.

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 22092-92-8 diisopropopylaminoborane 
• 1996-38-9 3-fluorobenzenediazonium tetrafluoroborate 
• 701-27-9 3-fluorobenzene-1-sulfonyl chloride 
• 935447-39-5 sodium 3-fluorobenzenesulfinate 
• 73183-34-3 bis(pinacol)diborane 
• 120579-23-9 diethyl (3-fluorophenyl) phosphate 
• 625-98-9 3-chlorofluorobenzene 
• 658-28-6 (3-fluorophenyl)(methyl)sulfide 
• 462-06-6 fluorobenzene 
• 372-18-9 1,3-Difluorobenzene 
• 557087-01-1 2-dimethylamino-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1073-06-9 3-fluorobromobenzene 
• 1121-86-4 1-Fluoro-3-iodobenzene 

Downstream Products

• 1533422-40-0 C₁₂H₁₃F₄NO₄S 

Relevant articles and documents

Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron

The desulfitative borylation reaction of sodium arylsulfinates with bis(pinacolato)diboron or bis(neopentylglycolato)diboron under palladium catalysis has been developed, allowing selective C-B bond formation to give arylboronates with a range of functional groups in moderate to good yields under mild reaction conditions. A gram-scale preparation as well as the cascade Suzuki-Miyaura cross-coupling of arylboronates demonstrated the potential practical utility in organic synthesis.

Unveiling Extreme Photoreduction Potentials of Donor-Acceptor Cyanoarenes to Access Aryl Radicals from Aryl Chlorides

Since the seminal work of Zhang in 2016, donor-acceptor cyanoarene-based fluorophores, such as 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN), have been widely applied in photoredox catalysis and used as excellent metal-free alternatives to noble metal Ir- and Ru-based photocatalysts. However, all the reported photoredox reactions involving this chromophore family are based on harnessing the energy from a single visible light photon, with a limited range of redox potentials from -1.92 to +1.79 V vs SCE. Here, we document the unprecedented discovery that this family of fluorophores can undergo consecutive photoinduced electron transfer (ConPET) to achieve very high reduction potentials. One of the newly synthesized catalysts, 2,4,5-tri(9H-carbazol-9-yl)-6-(ethyl(phenyl)amino)isophthalonitrile (3CzEPAIPN), possesses a long-lived (12.95 ns) excited radical anion form, 3CzEPAIPN?-*, which can be used to activate reductively recalcitrant aryl chlorides (Ered ≈ -1.9 to -2.9 V vs SCE) under mild conditions. The resultant aryl radicals can be engaged in synthetically valuable aromatic C-B, C-P, and C-C bond formation to furnish arylboronates, arylphosphonium salts, arylphosphonates, and spirocyclic cyclohexadienes.

Direct C?H Borylation of Arenes Catalyzed by Saturated Hydride-Boryl-Iridium-POP Complexes: Kinetic Analysis of the Elemental Steps

The saturated trihydride IrH3{κ3-P,O,P-[xant(PiPr2)2]} (1; xant(PiPr2)2=9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene) activates the B?H bond of two molecules of pinacolborane (HBpin) to give H2, the hydride-boryl derivatives IrH2(Bpin){κ3-P,O,P-[xant(PiPr2)2]} (2) and IrH(Bpin)2{κ3-P,O,P-[xant(PiPr2)2]} (3) in a sequential manner. Complex 3 activates a C?H bond of two molecules of benzene to form PhBpin and regenerates 2 and 1, also in a sequential manner. Thus, complexes 1, 2, and 3 define two cycles for the catalytic direct C?H borylation of arenes with HBpin, which have dihydride 2 as a common intermediate. C?H bond activation of the arenes is the rate-determining step of both cycles, as the C?H oxidative addition to 3 is faster than to 2. The results from a kinetic study of the reactions of 1 and 2 with HBpin support a cooperative function of the hydride ligands in the B?H bond activation. The addition of the boron atom of the borane to a hydride facilitates the coordination of the B?H bond through the formation of κ1- and κ2-dihydrideborate intermediates.