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

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

Downstream Products

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

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.

Single-Site Cobalt-Catalyst Ligated with Pyridylimine-Functionalized Metal-Organic Frameworks for Arene and Benzylic Borylation

We report a highly active single-site heterogeneous cobalt-catalyst based on a porous and robust pyridylimine-functionalized metal-organic frameworks (pyrim-MOF) for chemoselective borylation of arene and benzylic C-H bonds. The pyrim-MOF having UiO-68 topology, constructed from zirconium-cluster secondary building units and pyridylimine-functionalized dicarboxylate bridging linkers, was metalated with CoCl2 followed by treatment of NaEt3BH to give the cobalt-functionalized MOF-catalyst (pyrim-MOF-Co). Pyrim-MOF-Co has a broad substrate scope, allowing the C-H borylation of halogen-, alkoxy-, alkyl-substituted arenes as well as heterocyclic ring systems using B2pin2 or HBpin (pin = pinacolate) as the borylating agent to afford the corresponding arene- or alkyl-boronate esters in good yields. Pyrim-MOF-Co gave a turnover number (TON) of up to 2500 and could be recycled and reused at least 9 times. Pyrim-MOF-Co was also significantly more robust and active than its homogeneous control, highlighting the beneficial effect of active-site isolation within the MOF framework that prevents intermolecular decomposition. The experimental and computational studies suggested (pyrim?-)CoI(THF) as the active catalytic species within the MOF, which undergoes a mechanistic pathway of oxidative addition, turnover limiting σ-bond metathesis, followed by reductive elimination to afford the boronate ester.