325142-93-6

Usage

Uses

Used in Organic Synthesis:
2-(3,5-DIMETHYLPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE is used as a precursor for the preparation of various other organic compounds in the field of organic synthesis. Its stability and ability to participate in a variety of chemical reactions make it a versatile building block for synthesizing complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(3,5-DIMETHYLPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE is used as a key intermediate in the synthesis of pharmaceutical compounds. Its unique structure and properties contribute to the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
2-(3,5-DIMETHYLPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE is also used as a valuable tool in chemical research for studying reaction mechanisms, exploring new synthetic routes, and developing innovative methodologies in organic chemistry. Its unique structure and properties provide insights into the reactivity and selectivity of various chemical transformations.

InChI:InChI=1/C14H21BO2/c1-10-7-11(2)9-12(8-10)15-16-13(3,4)14(5,6)17-15/h7-9H,1-6H3

Upstream product

• 108-38-3 m-xylene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 745783-95-3 tert-butyldimethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 745783-97-5 triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 1075719-92-4 n-Bu₃SiB(pinacolate) 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 172975-69-8 3,5-dimethylphenyl boronic acid 
• 22445-41-6 3,5-dimethylphenyl iodide 
• 3742-75-4 3-phenylpropyl 4-methylbenzenesulfonate 
• 556-96-7 5-bromo-1,3-xylene 
• 1204393-81-6 C₁₄H₁₃BO₂ 
• 352-70-5 m-Fluorotoluene 
• 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

• 75934-26-8 N-(3,5-dimethylphenyl)-2-aminoacetaldehyde diethylacetal 
• 172975-69-8 3,5-dimethylphenyl boronic acid 
• 5369-25-5 bis-(3,5-dimethylphenyl)-amine 
• 51786-49-3 N-(3,5-dimethylphenyl)aniline 
• 556-96-7 5-bromo-1,3-xylene 
• 556-97-8 1-chloro-3,5-dimethylbenzene 
• 935552-89-9 3',5'-dimethyl-[1,1'-biphenyl]-4-carbonitrile 
• 25570-02-9 3,3',5,5'-tetramethyl-1,1'-biphenyl 
• 51839-12-4 3',5'-dimethyl-[1,1'-biphenyl]-2-amine 
• 1256781-60-8 2-(2-bromo-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1256781-70-0 2-(2-iodo-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1256781-74-4 2-(2-chloro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1228020-97-0 3-(3,5-dimethylphenyl)cyclohexanone 

Relevant academic research and scientific papers

Palladium-catalyzed ortho-C-H arylation of acetophenone oxime ethers with aryl pinacol boronic esters

We report an efficient palladium-catalyzed ortho-C-H arylation of acetophenone oxime ethers with aryl pinacol boronic esters, leading to the synthesis of biaryl derivatives in good yields. Sequential process of iridiumcatalyzed C-H borylation and palladiu

Merging Iridium-Catalyzed C-H Borylations with Palladium-Catalyzed Cross-Couplings Using Triorganoindium Reagents

A versatile and efficient method to prepare borylated arenes furnished with alkyl, alkenyl, alkynyl, aryl, and heteroaryl functional groups is developed by merging Ir-catalyzed C-H borylations (CHB) with a chemoselective palladium-catalyzed cross-coupling of triorganoindium reagents (Sarandeses-Sestelo coupling) with aryl halides bearing a boronic ester substituent. Using triorganoindium cross-coupling reactions to introduce unsaturated moieties enables the synthesis of borylated arenes that would be difficult to access through the direct application of the CHB methodology. The sequential double catalyzed procedure can be also performed in one vessel.

Cu-mediated: vs. Cu-free selective borylation of aryl alkyl sulfones

A Cu-catalysed borylation of aryl alkyl sulfones was developed for the high yield synthesis of versatile arylboronic esters using a readily prepared NHC-Cu catalyst. In addition, the selective cleavage of either alkyl(C)-sulfonyl or aryl(C)-sulfonyl bonds

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

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.

Photochemical and electrochemical C-N borylation of arylhydrazines

The C-N borylation of arylhydrazine hydrochlorides with bis(pinacolato)diboron was achieved under photochemical and electrochemical conditions, respectively. This novel and scalable transformation provides two efficient and mild transition-metal-free synt

Base-Free Pd-Catalyzed C?Cl Borylation of Fluorinated Aryl Chlorides

Catalytic C?X borylation of aryl halides containing two ortho-fluorines has been found to be challenging, as most previous methods require stoichiometric amounts of base and the polyfluorinated aryl boronates suffer from protodeboronation, which is accele

Engaging Ag(0) single atoms in silver(I) salts-mediated C-B and C-S coupling under visible light irradiation

Silver(I) salts were found active in the borylation and sulfenylation of aryl iodides under visible light irradiation. The optimized borylation protocol using AgF did not need any additive, operated under very mild conditions, and well tolerated a broad scope of substrates and boron sources. Formation of Ag(0) single atoms (AgSAs) during the borylation reactions was examined using high-angle annular dark field aberration-corrected scanning transmission electron microscope (HAADF AC-STEM) and electron paramagnetic resonance (EPR). The activities of the silver(I) salts were affected by the anions and could be associated with their abilities in formation of AgSAs during the reactions. Kinetic studies showed that the deiodination rate was linearly correlated with the loading of AgSAs, and hence AgSAs were the true catalytic centers for the 1e?-reduction of the C-I moieties. The oxidation state of AgSAs kept 0 in both the resting and the working states. A “work-in-tandem” mechanism involving AgSAs as the catalytic centers and AgNPs as the light absorber to achieve the borylation of aryl iodides under visible light irradiation is proposed. The current approach not only provides an alternative system for borylation and sulfenylation of aryl iodides, but also reveals a new activity of silver(I) salts involving AgSAs under visible light irradiation.

Preparation method of aryl borate catalyzed by cesium neovalerate

The preparation method comprises the following steps: dissolving a compound of formula (I) and a diboron compound in an organic solvent, then adding an organic solvent dissolved with cesium neovalerate, palladium acetate and triphenylphosphine, and carrying out reaction to obtain aryl boronic acid ester. In the formula (I) R1. R2, R3, R4 and R5 are each independently selected from H, C. 1 - C10 Alkyl group, C2 - C10 Alkenyl, C2 - C10 Alkynyl group, C1 - C10 Alkoxy, hydroxy, hydroxy-substituted C1 - C10 Alkyl, phenyl, C1 - C10 Alkylamino. X Is selected from F, Cl, Br, i. The preparation method has the advantages of low production cost, high product yield, high purity, simple operation and suitability for industrial mass production.

Design, Synthesis and Biological Evaluation of Boron-Containing Macrocyclic Polyamine Dimers and Their Zinc(II) Complexes for Boron Neutron Capture Therapy

Boron neutron capture therapy (BNCT) is considered to have potential for cancer therapy based on the nuclear reaction between boron (10B) atoms and thermal neutrons, yielding 4He2+ (α) and 7Li3+ ions.