1092060-77-9

Basic information

• Product Name: 2-(4-methylphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane
• Synonyms: 2-(4-methylphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane
• CAS NO: 1092060-77-9
• Molecular Weight: 218.104
• Mol File: 1092060-77-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 311.9±21.0 °C(Predicted)
• Density: 0.98±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2-(4-methylphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-methylphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane(1092060-77-9)
• EPA Substance Registry System: 2-(4-methylphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane(1092060-77-9)

Safety Data

• Hazardous Substances Data: 1092060-77-9(Hazardous Substances Data)

Usage

Boronic ester

A class of chemical compounds 2-(4-methylphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane is a boronic ester, which is a type of chemical compound containing a boron-oxygen bond.

Organic synthesis reagent

Used in cross-coupling reactions This compound is commonly used in organic synthesis as a reagent for cross-coupling reactions, which are chemical reactions that facilitate the formation of carbon-carbon bonds.

Production of various organic compounds

Capable of generating a wide variety of organic molecules The cross-coupling reactions involving 2-(4-methylphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane can produce a diverse range of organic compounds.

Unique structure

Characterized by its boron-oxygen bond The presence of a boron-oxygen bond in the structure of 2-(4-methylphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane contributes to its unique properties and applications.

Important intermediate

In the preparation of pharmaceuticals, agricultural chemicals, and materials science Due to its unique structure and reactivity, 2-(4-methylphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane serves as a crucial intermediate in the synthesis of various products in different fields.

Building block for complex organic molecules

Valuable for synthesizing complex organic compounds This compound is a useful building block in the synthesis of complex organic molecules, which can be further utilized in various applications.

Widely used in advanced materials and pharmaceuticals production

Contributes to the creation of advanced materials and pharmaceuticals 2-(4-methylphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane is an essential component in the production of advanced materials and pharmaceuticals due to its unique properties and applications.

Upstream product

• 230299-21-5 4,4,4',4',6,6'-hexamethyl-2,2'-bi(1,3,2-dioxaborinane)bis(hexyleneglycolato)diboron 
• 106-43-4 para-chlorotoluene 
• 107-41-5 2-methyl-2,4-pentanediol 
• 5720-05-8 4-methylphenylboronic acid 
• 106-45-6 para-thiocresol 
• 623-13-2 4-methylphenyl methylsulfide 
• 10199-14-1 4,4,6-trimethyl-1,3,2-dioxaborinane 
• 29540-83-8 p-tolyl triflate 
• 624-31-7 4-tolyl iodide 
• 106-38-7 para-bromotoluene 

Downstream Products

• 644-08-6 4-Methylbiphenyl 
• 53040-92-9 4-(4-tolyl)anisole 
• 3717-68-8 1-methyl-4-(1-phenylethyl)benzene 
• 55707-02-3 1-chloro-3-(p-tolyl)-3-phenylpropane 

Relevant articles and documents

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.

Palladium-Catalyzed ipso-Borylation of Aryl Sulfides with Diborons

A catalytic Miyaura-type ipso-borylation of aryl sulfides with diboron reagents has been achieved, providing arylboronate esters of synthetic use. The key conditions to transform inherently reluctant C-S bonds into C-B bonds include a palladium-NHC (N-heterocyclic carbene) precatalyst, bis(pinacolato)diboron, and lithium hexamethyldisilazide. This protocol is applicable to a reasonable range of aryl alkyl sulfides. Twofold borylation was observed in the reaction of diphenyl sulfide.

Improved preparation of 4,6,6-trimethyl-1,3,2-dioxaborinane and its use in a simple [PdCl2(TPP)2]-catalyzed borylation of aryl bromides and iodides

We describe a convenient preparation of 4,6,6-trimethyl-1,3,2-dioxaborinane (MethylPentaneDiolBorane, MPBH) and demonstrate that it is an excellent reagent for the [PdCl2(PPh3)2]-catalyzed borylation of aryl bromides and iodides. The corresponding boronic esters undergo rapid Suzuki coupling reactions in the presence of cesium fluoride. Thus, MPBH is an excellent alternative to pinacolborane for Pd-catalyzed borylation and cross-coupling reactions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.