754226-39-6

Basic information

• Product Name: 2-(3,4-Difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane
• Synonyms: 2-(3,4-Difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane
• CAS NO: 754226-39-6
• Molecular Formula: C₁₂H₁₅BF₂O₂
• Molecular Weight: 240.0541064
• Mol File: 754226-39-6.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(3,4-Difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-Difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(754226-39-6)
• EPA Substance Registry System: 2-(3,4-Difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(754226-39-6)

Safety Data

• Hazardous Substances Data: 754226-39-6(Hazardous Substances Data)

Usage

General Description

2-(3,4-Difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is a chemical compound with the molecular formula C13H16BF2O2. It is a boron-based compound that contains a dioxaborolane ring structure. 2-(3,4-Difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is commonly used in organic synthesis as a reagent for the direct arylation of heterocycles and as a precursor for the synthesis of various pharmaceuticals and agrochemicals. It is also used in the production of organic light-emitting diodes (OLEDs) and other advanced electronic materials. This chemical has potential applications in the fields of medicinal chemistry, materials science, and chemical research.

Upstream product

• 348-61-8 1-bromo-3,4-difluorobenzene 
• 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 
• 3863-11-4 3,4-difluoroaniline 
• 367-11-3 ortho-difluorobenzene 
• 367-23-7 1,2,4-trifluorobenzene 
• 455-86-7 3,4-Difluorobenzoic acid 
• 64248-58-4 1,2-difluoro-4-iodo-benzene 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 

Downstream Products

• 1469858-52-3 2-(3,4-difluorophenyl)-6-(4-methoxyphenyl)-4-(2-trimethylsilanylethoxymethyl)-4,7-dihydro-1-thia-4,5-diazacyclopenta[a]pentalene 

Relevant articles and documents

Palladium-Catalyzed Decarbonylative Borylation of Carboxylic Acids: Tuning Reaction Selectivity by Computation

Decarbonylative borylation of carboxylic acids is reported. Carbon electrophiles are generated directly after reagent-enabled decarbonylation of the in situ accessible sterically-hindered acyl derivative of a carboxylic acid under catalyst controlled conditions. The scope and the potential impact of this method are demonstrated in the selective borylation of a variety of aromatics (>50 examples). This strategy was used in the late-stage derivatization of pharmaceuticals and natural products. Computations reveal the mechanistic details of the unprecedented C?O bond activation of carboxylic acids. By circumventing the challenging decarboxylation, this strategy provides a general synthetic platform to access arylpalladium species for a wide array of bond formations from abundant carboxylic acids. The study shows a powerful combination of experiment and computation to predict decarbonylation selectivity.

Cobalt-Catalyzed C(sp2)-H borylation with an air-stable, readily prepared terpyridine cobalt(II) Bis(acetate) precatalyst

A bench-stable, 4-aryl-substituted terpyridine supported, high-spin cobalt(II) bis(acetate) complex, (ArTpy)Co- (OAc)2 (ArTpy = 4′-(4-N,N′-dimethylaminophenyl)-2,2′:6′,2″- Terpyridine), is active for the C(sp2)-H borylation of arenes and heteroarenes with B2Pin2 (Pin = pinacolato). Optimization of the catalytic borylation reaction revealed improved performance in the presence of LiOMe and turnover numbers of up to 100 have been observed using all air-stable components. EPR specstroscopy identified formation of inactive cobalt species, promoted by excess HBPin. A high-spin cobalt(II) bis[(diacetoxy)- pinacolatoborate-κ3O,O,O] compound has been isolated and characterized by X-ray diffraction and is the result of catalyst deactivation.

Chemoselective coupling of 1,1-bis[(pinacolato)boryl]alkanes for the transition-metal-frec borylation of aryl and vinyl halides: A combined experimental and theoretical investigation

A new transition-metal-frec borylation of aryl and vinyl halides using l,l-bis[(pinacolato)boryl]alkanes as boron sources is described. In this transformation one of the boron groups from 1,1-bis[(pinacolato)boryl]alkanes is selectively transferred to aryl and vinyl halides in the presence of sodium tert-butoxide as the only activator to form organoboronate esters. Under the developed borylation conditions, a broad range of organohalides are borylated with excellent chemo-selectivity and functional group compatibility, thus offering a rare example of a transition-metal-frec borylation protocol. Experimental and theoretical studies have becn performed to elucidate the reaction mechanism, revealing the unusual formation of Lewis acid/base adduct betwecn organohalides and α-borylcarbanion, generated in situ from the reaction of l,l-bis[(pinacolato)boryl]alkanes with an alkoxide base, to facilitate the borylation reactions.