1451393-45-5

Basic information

• Product Name: 2-Bromo-4-chlorophenylboronic acid
• Synonyms: 2-Bromo-4-chlorophenylboronic acid
• CAS NO: 1451393-45-5
• Molecular Formula: C₆H₅BBrClO₂
• Molecular Weight: 235.2707
• Mol File: 1451393-45-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Bromo-4-chlorophenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4-chlorophenylboronic acid(1451393-45-5)
• EPA Substance Registry System: 2-Bromo-4-chlorophenylboronic acid(1451393-45-5)

Safety Data

• Hazardous Substances Data: 1451393-45-5(Hazardous Substances Data)

Usage

General Description

2-Bromo-4-chlorophenylboronic acid is a chemical compound with the molecular formula C6H5BClBrO2. It consists of a phenylboronic acid core that is substituted with a bromine atom at the 2-position and a chlorine atom at the 4-position. 2-Bromo-4-chlorophenylboronic acid is commonly used in organic synthesis as a building block for creating various aromatic boronic acids, which are essential intermediates in the production of pharmaceuticals, agrochemicals, and materials. It is also used in the development of catalysts and as a reagent in chemical research. Additionally, 2-Bromo-4-chlorophenylboronic acid is known for its ability to react with aryl chlorides and bromides in palladium-catalyzed coupling reactions, making it an important tool in cross-coupling chemistry.

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 articles and documents

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.

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.