401797-00-0

Basic information

• Product Name: 3,4-Dimethylphenylboronic acid pinacol ester
• Synonyms: 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3,4-Dimethylphenylboronic acid pinacol ester;3,4-DiMethylbenzeneboronic acid pinacol ester;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-o-xylene
• CAS NO: 401797-00-0
• Molecular Formula: C14H21BO2
• Molecular Weight: 250.14162
• Mol File: 401797-00-0.mol
• Article Data: 43

Chemical Properties

• Boiling Point: 325.4 °C at 760 mmHg
• Flash Point: 150.6 °C
• Appearance: /
• Density: 0.97 g/cm³
• Storage Temp.: Room temperature.
• CAS DataBase Reference: 3,4-Dimethylphenylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dimethylphenylboronic acid pinacol ester(401797-00-0)
• EPA Substance Registry System: 3,4-Dimethylphenylboronic acid pinacol ester(401797-00-0)

Safety Data

• Hazardous Substances Data: 401797-00-0(Hazardous Substances Data)

Usage

General Description

3,4-Dimethylphenylboronic acid pinacol ester is a chemical compound that is commonly used as a reagent in organic synthesis. It is a boronic ester, which means it contains a boron atom bonded to an organic group and an alcohol group. 3,4-Dimethylphenylboronic acid pinacol ester is often used in Suzuki-Miyaura cross-coupling reactions, which are important in the synthesis of pharmaceuticals, agrochemicals, and materials science. The pinacol ester moiety in this compound refers to the presence of a pinacol group, which is a type of bridging group consisting of two hydroxyl groups bonded to the same carbon atom. 3,4-Dimethylphenylboronic acid pinacol ester is a valuable building block in organic chemistry due to its ability to participate in a variety of important reactions.

Upstream product

• 95-47-6 o-xylene 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 95-65-8 3,4-Dimethylphenol 
• 1314020-40-0 1-methylsulfonyloxy-3,4-dimethylbenzene 
• 931-88-4 1,2-cyclooctene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 16557-41-8 3,4-(CH₃)2C₆H₃BCl₂ 
• 95-64-7 4-amino-o-xylene 
• 615-60-1 4-chloro-1,2-dimethylbenzene 
• 583-71-1 4-bromo-o-xylene 
• 55499-43-9 3,4-dimethyl phenylboronic acid 
• 770-03-6 N,N,3,4-tetramethylaniline 
• 60481-51-8 3,4-dimethylphenylhydrazine hydrochloride 

Relevant articles and documents

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

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.

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.