288101-48-4

Basic information

• Product Name: 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,5-DIFLUOROBENZENE
• Synonyms: 2-(2,4-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2,4-DIFLUOROPHENYLBORONIC ACID, PINACOL ESTER;2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,5-DIFLUOROBENZENE
• CAS NO: 288101-48-4
• Molecular Formula: C₁₂H₁₅BF₂O₂
• Molecular Weight: 240.05
• Product Categories: Heterocyclic Compounds
• Mol File: 288101-48-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 41-44 °C(lit.)
• Boiling Point: 276.5°Cat760mmHg
• Flash Point: 226 °F
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 0.00805mmHg at 25°C
• Refractive Index: 1.468
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,5-DIFLUOROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,5-DIFLUOROBENZENE(288101-48-4)
• EPA Substance Registry System: 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,5-DIFLUOROBENZENE(288101-48-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 288101-48-4(Hazardous Substances Data)

Usage

General Description

The chemical compound "2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,5-difluorobenzene" is a boron-containing aromatic compound that is commonly used in organic synthesis and materials science. It is a white solid with a molecular formula of C14H17BF2O and a molecular weight of 255.09 g/mol. 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,5-DIFLUOROBENZENE is often used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and advanced materials. It is also used as a precursor in the production of boron-containing polymers and as a reagent in organic reactions. Additionally, its unique structure and properties make it an interesting target for research and development in the field of organic chemistry.

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

Upstream product

• 367-23-7 1,2,4-trifluorobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 372-18-9 1,3-Difluorobenzene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 348-57-2 2,4-difluorobromobenzene 

Downstream Products

• 1268613-36-0 C₃₀H₁₆F₄N₄ 
• 917495-77-3 2-(2',4'-difluorophenyl)-4-bromopyridine 
• 1207723-92-9 6-(2,4-difluorophenyl)pyrimidine-4-carboxylic acid methyl ester 
• 372-18-9 1,3-Difluorobenzene 
• 872545-53-4 2,4,4'-trifluoro-1,1'-biphenyl 
• 391604-55-0 2-(2,4-difluorophenyl)pyridine 
• 736987-78-3 trans-2-(2,4-difluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

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.

Miyaura Borylation and One-Pot Two-Step Homocoupling of Aryl Chlorides and Bromides under Solvent-Free Conditions

Solvent-free protocols for Miyaura borylation and the one-pot, two-step homocoupling of aryl halides are reported for the first time. Bis(dibenzylideneacetone)palladium(0) [Pd(dba)2] is an optimal source of palladium for Miyaura borylation, while for one-pot two-step homocoupling palladium(II) acetate [Pd(OAc)2] gives highest yields. Aryl bromides are coupled most efficiently using the DPEphos ligand. Chlorides are coupled using XPhos. The developed protocols are robust, versatile and easily reproducible on a large scale.