• 1. Design, synthesis and evaluation of novel tetrahydrothieno[3,2-c]pyridine derivatives as potent smoothened antagonists
  Xiaofeng Chen,Chiyu Sun,Jingzhou Zhang,Huaiwei Ding,Hongrui Song Med. Chem. Commun. 2016 7 960

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoyl derivatives
• Solvents and Organic Chemicals Organic Compounds Aldehyde/Ketone

5-Bromo-2-chlorobenzaldehyde (CAS No. 189628-37-3): A Versatile Building Block in Organic Synthesis

5-Bromo-2-chlorobenzaldehyde (CAS 189628-37-3) is a highly valuable aromatic aldehyde compound that serves as a crucial intermediate in pharmaceutical and agrochemical synthesis. This brominated chlorobenzaldehyde derivative features both bromo and chloro substituents on the benzene ring, making it particularly reactive for various coupling reactions and functional group transformations.

The molecular structure of 5-bromo-2-chloro benzaldehyde contains two distinct halogen atoms at the 5- and 2-positions respectively, with an aldehyde group at position 1. This unique arrangement enables the compound to participate in multiple reaction pathways, including Suzuki-Miyaura cross-coupling, nucleophilic aromatic substitution, and reductive amination. Recent studies highlight its growing importance in developing new drug candidates and advanced materials.

In pharmaceutical applications, 5-bromo-2-chlorobenzaldehyde CAS 189628-37-3 has been utilized as a key precursor for synthesizing various biologically active molecules. Researchers have employed this compound in the development of potential kinase inhibitors, antimicrobial agents, and central nervous system therapeutics. The presence of both bromine and chlorine atoms allows for selective modification of the aromatic ring, enabling medicinal chemists to create diverse molecular architectures.

The material science field has also benefited from 5-bromo-2-chlorobenzaldehyde applications. Its incorporation into organic electronic materials and liquid crystal compounds has shown promising results in improving device performance. The compound's ability to form stable conjugated systems makes it valuable for developing OLED materials and photovoltaic components, aligning with current research trends in sustainable energy solutions.

From a synthetic chemistry perspective, 5-bromo-2-chloro benzaldehyde offers several advantages. The bromine atom serves as an excellent leaving group for metal-catalyzed cross-coupling reactions, while the chlorine atom provides additional stability to the molecular structure. The aldehyde functionality enables straightforward conversion to various other functional groups, including alcohols, acids, and imines, making it a versatile synthetic building block.

Recent market analysis indicates growing demand for 5-bromo-2-chlorobenzaldehyde CAS 189628-37-3, particularly from the pharmaceutical and specialty chemicals sectors. Manufacturers are focusing on developing more efficient synthesis routes to meet the increasing requirements from research institutions and industrial laboratories. The compound's stability under standard storage conditions and well-characterized properties contribute to its popularity among synthetic chemists.

Quality control aspects of 5-bromo-2-chlorobenzaldehyde production have gained attention, with analytical methods such as HPLC, GC-MS, and NMR spectroscopy being routinely employed to ensure high purity standards. The compound typically appears as a white to pale yellow crystalline solid with characteristic aromatic and aldehyde properties. Proper handling and storage recommendations include protection from moisture and light to maintain stability.

Environmental considerations regarding brominated chlorobenzaldehyde derivatives have led to increased research into greener synthetic approaches. Recent advancements include catalytic methods that minimize waste generation and improve atom economy in the production of 5-bromo-2-chloro benzaldehyde. These developments align with the pharmaceutical industry's growing emphasis on sustainable chemistry practices.

Future research directions for 5-bromo-2-chlorobenzaldehyde CAS 189628-37-3 may explore its potential in emerging fields such as bioconjugation chemistry and targeted drug delivery systems. The compound's structural features make it suitable for creating molecular probes and diagnostic agents, opening new possibilities in biomedical applications. Continued investigation of its reactivity patterns will likely reveal additional synthetic utilities.

For researchers working with 5-bromo-2-chlorobenzaldehyde, proper characterization techniques are essential. Fourier-transform infrared spectroscopy (FTIR) can confirm the presence of the aldehyde carbonyl group, while ¹H and ¹³C NMR provide detailed structural information about the aromatic system and substituent positions. Mass spectrometry serves as a valuable tool for purity assessment and structural confirmation.

The commercial availability of 5-bromo-2-chlorobenzaldehyde CAS 189628-37-3 from multiple chemical suppliers has facilitated its widespread use in academic and industrial settings. Current market trends show stable pricing for this intermediate, with packaging options ranging from gram-scale quantities for research purposes to kilogram amounts for process development. Suppliers typically provide comprehensive technical data sheets and certificates of analysis.

In conclusion, 5-bromo-2-chlorobenzaldehyde represents an important chemical building block with diverse applications across multiple scientific disciplines. Its unique combination of bromine and chlorine substituents, along with the reactive aldehyde group, makes it particularly valuable for synthetic chemistry applications. As research continues to uncover new uses for this compound, its significance in medicinal chemistry and materials science is expected to grow further.

• 1114808-98-8(6-Bromo-2-chloro-3-methylbenzaldehyde)
• 1114809-00-5(2-Bromo-6-chloro-3-methylbenzaldehyde)
• 1349716-93-3(4-Bromo-2,5-dichlorobenzaldehyde)
• 188813-05-0(3-Bromo-5-chlorobenzaldehyde)
• 64622-16-8(2-Bromo-6-chlorobenzaldehyde)
• 158435-41-7(4-Bromo-2-chlorobenzaldehyde)
• 105884-19-3(1-(5-bromo-2-chlorophenyl)ethan-1-one)
• 21900-52-7(5-bromo-2-chlorobenzoyl chloride)
• 1197050-28-4(3-Bromo-2-chlorobenzaldehyde)
• 86265-88-5(3-Bromo-4-chlorobenzaldehyde)