1451393-45-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-4-chlorophenylboronic acid is used as a key intermediate for the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Bromo-4-chlorophenylboronic acid is utilized as a building block for the synthesis of agrochemicals, contributing to the development of more effective and environmentally friendly pesticides and herbicides.
Used in Materials Science:
2-Bromo-4-chlorophenylboronic acid is employed as a precursor in the synthesis of advanced materials, such as polymers and composites, with tailored properties for various applications in materials science.
Used in Catalyst Development:
2-Bromo-4-chlorophenylboronic acid is used as a component in the development of catalysts, which are essential for accelerating chemical reactions in various industrial processes, including the production of fine chemicals and pharmaceuticals.
Used in Chemical Research:
2-Bromo-4-chlorophenylboronic acid serves as a reagent in chemical research, enabling scientists to explore new reaction pathways and develop innovative synthetic methods.
Used in Cross-Coupling Chemistry:
2-Bromo-4-chlorophenylboronic acid is an important tool in palladium-catalyzed cross-coupling reactions, allowing for the formation of carbon-carbon and carbon-heteroatom bonds. This capability is crucial for the synthesis of complex organic molecules and the construction of molecular frameworks in various chemical and pharmaceutical applications.

Upstream product

• 31928-44-6 2-bromo-4-chloroiodobenzene 
• 5419-55-6 Triisopropyl borate 
• 121-43-7 Trimethyl borate 
• 150-46-9 triethyl borate 

Downstream Products

• 1256781-67-5 2-(2-bromo-4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 2523-44-6 2-chloro-9H-fluorene 

Relevant academic research and scientific papers

Modular Synthesis of Pentagonal and Hexagonal Ring-Fused NBN-Phenalenes Leading to an Excited-State Aromatization-Induced Structural Planarization Molecular Library

Although polycyclic aromatic hydrocarbons (PAHs) with a nitrogen-boron-nitrogen (NBN) moiety have recently attracted tremendous interest due to their intriguing electronic and optoelectronic properties, all of the NBN-fused π-systems reported to date are called NBN-dibenzophenalenes and were synthesized by electrophilic aromatic substitution. The synthesis of NBN-phenalenes remains challenging, and transition-metal catalysis has never been utilized to construct NBN-embedded π-scaffolds. Herein, a palladium-catalyzed cyclization/bicyclization strategy was developed for the synthesis of diverse pentagonal and hexagonal ring-fused NBN-phenalenes and half-NBN-phenalenes. All of the NBN-embedded π-scaffolds presented in our paper are fluorescent in both solution and the solid state. Further investigations showed that the five-membered NBN rings exhibit the properties of traditional luminogens, while those with a six-membered NBN ring generally undergo photoinduced structural planarization (PISP) and exhibit different colors and quantum yields of fluorescence with different concentrations in solution. Time-resolved spectroscopy and TD-DFT calculations revealed that excited-state aromatization is the driving force for PISP in hexagonal ring-fused NBN-πsystems, leading to the formation of excimers. Notably, the scope of PISP compounds is still quite limited, and PISP has never been observed in NBN-πsystems before. These hexagonal ring-fused NBN-πsystems constitute a novel PISP molecular library and appear to be a new class of aggregation-induced excimer emission (AIEE) materials. Finally, the AIEE behavior of these six-membered NBN rings was applied to the detection of nitro explosives, achieving excellent sensitivity. In general, this work provides a new viewpoint for synthesizing NBN-fused π-systems and understanding the excited-state motion of luminogens.

Synthesis of Biphenylenes and Their Higher Homologues by Cyclization of Aryne Derivatives

This investigation demonstrates that a series of biphenylenes can be easily prepared from their corresponding halobiphenyls by the cyclization of in situ generated 2′,3′-didehydro-2-lithiobiphenyls at low temperature. Two remarkable advantages of this synthetic method include 1) the lack of any need for transition-metal catalysts or reagents in the cyclization, and 2) the ability to obtain C1-functionalized products by treating the reaction intermediate 1-lithiobiphenylene with an electrophilic reagent. π-Extended derivatives, such as benzobiphenylenes, dibenzobiphenylene, linear/angular [3]phenylenes, and biphenyleno[2,3-b]biphenylenes, were synthesized similarly using suitable biaryls or teraryls.

Cyclic Diaryl λ3-Bromanes as Original Aryne Precursors

Despite the widespread application of hypervalent iodines, the corresponding λ3-bromanes are less explored. Herein we report a general, safe, and high-yielding strategy to access cyclic diaryl λ3-bromanes. These unique compounds feature reactivity that is appealing and complementary to that of λ3-iodanes, generating arynes under mild reaction conditions and in the presence of a weak base. Accordingly, formal meta-selective transition-metal-free C–O and C–N couplings may be achieved. Mechanistic studies unambiguously support the aryne generation mechanism.

Use of 2-bromophenylboronic esters as benzyne precursors in the Pd-catalyzed synthesis of triphenylenes

ortho-Substituted aryl boronates are introduced as aryne precursors for transition-metal-catalyzed transformations. On treatment with tBuOK and Pd(0), metal-bound aryne intermediates are formed that undergo effective trimerization to form useful triphenylene compounds. For meta-substituted arynes, the 3:1 product ratio in favor of non-C3 symmetric material is indicative of a benzyne mechanism.