356570-53-1

Basic information

• Product Name: 2-(2,5-Dimethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
• Synonyms: 2-(2,5-Dimethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
• CAS NO: 356570-53-1
• Molecular Formula: C₁₄H₂₁BO₂
• Molecular Weight: 232.12634
• Mol File: 356570-53-1.mol
• Article Data: 28

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2,5-Dimethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,5-Dimethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane(356570-53-1)
• EPA Substance Registry System: 2-(2,5-Dimethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane(356570-53-1)

Safety Data

• Hazardous Substances Data: 356570-53-1(Hazardous Substances Data)

Usage

General Description

2-(2,5-Dimethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane is a chemical compound that belongs to the class of boron-containing compounds. It is commonly used in organic synthesis as a reagent for the borylation of organic substrates. 2-(2,5-Dimethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane is known for its stability and ease of handling, making it a popular choice for various chemical reactions. It is also used in the production of pharmaceuticals and agrochemicals, as well as in the development of new materials and fine chemicals. Additionally, this compound has potential applications in the field of organic electronics and optoelectronics due to its unique properties.

Upstream product

• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 553-94-6 4-bromo-m-xylene 
• 95-72-7 2-chloro-1,4-dimethyl-benzene 
• 73183-34-3 bis(pinacol)diborane 
• 95-87-4 2,5-Dimethylphenol 
• 25240-59-9 pinacolboronic acid 
• 79644-40-9 2,5-dimethylphenyl trifluoromethanesulfonate 
• 106-42-3 para-xylene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 95-78-3 2,5-Dimethylaniline 

Downstream Products

• 420834-68-0 2-[1,4-bis(bromomethyl)]phenyl-9,9-dihexylfluorene 
• 420834-67-9 2-(2,5-dimethyl-phenyl)-9,9-dihexyl-9H-fluorene 
• 955935-14-5 2-{4-[2,5-bis(bromomethyl)phenyl]phenyl}-5-[3-(3,7-dimethyloctyloxy)phenyl]-1,3,4-oxadiazole 
• 955935-13-4 2-[3-(3,7-dimethyloctyloxy)phenyl]-5-[4-(2,5-dimethylphenyl)phenyl]-1,3,4-oxadiazole 
• 872599-88-7 2-(4-(2,3,4,5-tetraphenylphenyl)phenyl)-1,4-di(bromomethyl)benzene 
• 872599-87-6 2-(4-(2,3,4,5-tetraphenylphenyl)phenyl)-1,4-dimethylbenzene 
• 553-94-6 4-bromo-m-xylene 
• 420834-66-8 2-(2,5-dimethyl-phenyl)-9H-fluorene 

Relevant articles and documents

Mono-Phosphine Metal-Organic Framework-Supported Cobalt Catalyst for Efficient Borylation Reactions

We report a metal-organic framework (MOF) supported monoligated phosphine-cobalt complex, which is an active heterogeneous catalyst for aromatic C?H borylation and alkene hydroboration. The mono(phosphine)-Co catalyst (MOF?P?Co) was prepared by metalation of a porous triarylphosphine-functionalized MOF (MOF?P) with CoCl2 followed by activation with NaEt3BH. The MOF catalyst has a broad substrate scope with excellent functional group tolerance to afford arene- and alkyl-boronate esters in excellent yields and selectivity. MOF?P?Co gave a turnover number (TON) of 30,000 and could be recycled and reused at least 13 times in arene C?H borylation. Importantly, the attempt to prepare the homogeneous control (Ph3P?Co) using triphenylphosphine was unsuccessful due to the facile disproportionation reactions or intermolecular ligand exchanges in the solution. In contrast, the site isolation of the active mono(phosphine)-Co species within the MOF affords the robust and coordinatively unsaturated metal complexes, allowing to explore their catalytic properties and the reaction mechanism.

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.

Iridium-Catalyzed sp3 C-H Borylation in Hydrocarbon Solvent Enabled by 2,2′-Dipyridylarylmethane Ligands

Iridium-catalyzed alkane C-H borylation has long suffered from poor atom economy, resulting from both the inclusion of only 1 equiv of boron from the diboron reagent and a requirement for neat substrate. An appropriately substituted dipyridylarylmethane ligand was found to give highly active alkane borylation catalysts that facilitate C-H borylation with improved efficiency. This system provides for complete consumption of the diboron reagent, producing 2 molar equivalents of product at low catalyst loadings. The superior efficacy of this system also enables borylation of unactivated alkanes in hydrocarbon solvent with a reduced excess of substrate and improved functional group compatibility. The effectiveness of this ligand is displayed across a selection of functional groups, both under traditional borylation conditions in neat substrate and under atypical conditions in cyclohexane solvent. The utility of this catalytic system is exemplified by the borylation of substrates containing polar functionality, which are unreactive toward C-H borylation under neat conditions.