863868-37-5

Basic information

• Product Name: 2,6-DifluoroBenzeneBoronicacid,pinacolester
• Synonyms: 2-(2,6-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaBorolane;2,6-DifluoroBenzeneBoronicacid,pinacolester;2,6-Difluorophenylboronic acid, pinacol ester;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen (2,6-difluorophenyl)boronate;2,6-DifluoroBenzeneBoronicacid,picolester;1,3,2-Dioxaborolane, 2-(2,6-difluorophenyl)-4,4,5,5-tetramethyl-
• CAS NO: 863868-37-5
• Molecular Formula: C12H15BF2O2
• Molecular Weight: 240.0541064
• Product Categories: blocks;BoronicAcids
• Mol File: 863868-37-5.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 281.7°C at 760 mmHg
• Flash Point: 124.2°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 0.00599mmHg at 25°C
• Refractive Index: 1.468
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2,6-DifluoroBenzeneBoronicacid,pinacolester(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DifluoroBenzeneBoronicacid,pinacolester(863868-37-5)
• EPA Substance Registry System: 2,6-DifluoroBenzeneBoronicacid,pinacolester(863868-37-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 863868-37-5(Hazardous Substances Data)

Usage

General Description

2,6-DifluoroBenzeneBoronicacid,pinacolester is a chemical compound with the molecular formula C12H14BF2O2. It is a boronic acid ester derivative with a 2,6-difluorophenyl group. 2,6-DifluoroBenzeneBoronicacid,pinacolester is commonly used in organic synthesis as a reagent for the preparation of pharmaceuticals and agrochemicals. It is also utilized in the production of dyes, polymers, and electronic materials. The presence of the boronic acid functional group allows it to participate in versatile and important reactions, making it a valuable tool in the field of chemical research and development.

InChI:InChI=1/C12H15BF2O2/c1-11(2)12(3,4)17-13(16-11)10-8(14)6-5-7-9(10)15/h5-7H,1-4H3

Upstream product

• 64248-56-2 1-bromo-2,6-difluorobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 162101-25-9 2,6-difluorophenylboronic acid 
• 38361-37-4 1-chloro-2,6-difluorobenzene 
• 372-18-9 1,3-Difluorobenzene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 372-38-3 1,3,5-trifluorobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 1588422-60-9 3-(2,6-difluorophenyl)-1-ethyl-7-((5-fluoropyridin-2-yl)amino)-1,6-naphthyridin-2(1H)-one 
• 1415919-92-4 2,2’,6,6’-tetrafluoroazobenzene 

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.

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.

C-H borylation by platinum catalysis

Herein, we describe the platinum-catalyzed borylation of aromatic C-H bonds. N-Heterocyclic carbene-ligated platinum catalysts are found to be efficient catalysts for the borylation of aromatic C(sp2)-H bonds when bis(pinacolato)diboron is used as the boron source. The most remarkable feature of these Pt catalysts is their lack of sensitivity towards the degree of steric hindrance around the C-H bonds undergoing the borylation reaction. These Pt catalysts allow for the synthesis of sterically congested 2,6-disubstituted phenylboronic esters, which are otherwise difficult to synthesize using existing C-H borylation methods. Furthermore, platinum catalysis allows for the site-selective borylation of the C-H bonds ortho to fluorine substituents in fluoroarene systems. Preliminary mechanistic studies and work towards the synthetic application of this platinum catalyzed C-H borylation process are described.