876062-39-4

Basic information

• Product Name: 2-FLUOROPHENYLBORONIC ACID, PINACOL ESTER
• Synonyms: 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)FLUOROBENZENE;2-FLUOROPHENYLBORONIC ACID, PINACOL ESTER;AKOS BRN-1131;2-(2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;REF DUPL: 2-Fluorophenylboronic acid pinacol ester;1,3,2-Dioxaborolane, 2-(2-fluorophenyl)-4,4,5,5-tetramethyl-
• CAS NO: 876062-39-4
• Molecular Formula: C12H16BFO2
• Molecular Weight: 222.06
• Mol File: 876062-39-4.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 284.6±23.0℃ (760 Torr)
• Flash Point: 125.9±22.6℃
• Appearance: /
• Density: 1.05±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: 1.4830 to 1.4870
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-FLUOROPHENYLBORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FLUOROPHENYLBORONIC ACID, PINACOL ESTER(876062-39-4)
• EPA Substance Registry System: 2-FLUOROPHENYLBORONIC ACID, PINACOL ESTER(876062-39-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 876062-39-4(Hazardous Substances Data)

Usage

General Description

2-Fluorophenylboronic acid, pinacol ester is a chemical compound that is used in organic synthesis and pharmaceutical research. It is a boronic acid derivative that contains a fluorine atom and a pinacol ester group. Boronic acids are important building blocks for the construction of carbon-carbon bonds in organic synthesis, and the fluorine atom can impart specific chemical and biological properties to the compound. The pinacol ester group provides stability and protection for the boronic acid functionality. 2-FLUOROPHENYLBORONIC ACID, PINACOL ESTER is a valuable tool for chemists and researchers working in the field of medicinal chemistry and drug discovery.

InChI:InChI=1/C12H16BFO2/c1-11(2)12(3,4)16-13(15-11)9-7-5-6-8-10(9)14/h5-8H,1-4H3

Upstream product

• 462-06-6 fluorobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 73183-34-3 bis(pinacol)diborane 
• 367-11-3 ortho-difluorobenzene 
• 393-52-2 2-Fluorobenzoyl chloride 
• 1111096-19-5 2-(2,6-difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 325143-04-2 4,4,5,5-tetramethyl-2-(2,4,6-trifluorophenyl)-1,3,2-dioxaborolane 
• 832114-00-8 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole 
• 863868-37-5 2-(2,6-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis

The kinetics and mechanism of the base-catalyzed hydrolysis (ArB(OR)2→ ArB(OH)2) and protodeboronation (ArB(OR)2→ ArH) of a series of boronic esters, encompassing eight different polyols and 10 polyfluoroaryl and heteroaryl moieties, have been investigated by in situ and stopped-flow NMR spectroscopy (19F,1H, and11B), pH-rate dependence, isotope entrainment,2H KIEs, and KS-DFT computations. The study reveals the phenomenological stability of boronic esters under basic aqueous-organic conditions to be highly nuanced. In contrast to common assumption, esterification does not necessarily impart greater stability compared to the corresponding boronic acid. Moreover, hydrolysis of the ester to the boronic acid can be a dominant component of the overall protodeboronation process, augmented by self-, auto-, and oxidative (phenolic) catalysis when the pH is close to the pKaof the boronic acid/ester.

Organic compound, and organic electroluminescent device and electronic device using same

The invention relates to an organic compound. The structure of the organic compound comprises a formula I. When the organic compound provided by the invention is used for a light-emitting layer of anorganic electroluminescent device, the device efficiency of the device can be effectively improved, and the service life of the organic electroluminescent device is prolonged.

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.