• 1. Acenaphthenic hopanoids, a novel series of aromatised
  Teresita Carrillo-Hernández,Philippe Schaeffer,Pierre Albrecht Chem. Commun., 2001, 1976-1977
• 2. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
  Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?o Chem. Commun., 2015,51, 3993-3996
• 3. An approach to biodegradable star polymeric architectures using disulfide coupling?
  Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. Davis Chem. Commun., 2008, 6582-6584
• 4. An analyte-triggered artificial peroxidase system based on dimanganese complex for a versatile enzyme assay?
  Suji Lee,Min Su Han Chem. Commun., 2021,57, 9450-9453
• 5. An air-stable organometallic polymer containing titanafluorene moieties obtained by the Sonogashira–Hagihara cross-coupling polycondensation?
  Alvin Tanudjaja,Shinsuke Inagi,Fusao Kitamura,Toshikazu Takata,Ikuyoshi Tomita Dalton Trans., 2021,50, 3037-3043

Introduction to 2-Bromo-N-cyclopropyl-4-nitroaniline (CAS No: 1250973-55-7)

2-Bromo-N-cyclopropyl-4-nitroaniline is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound, identified by its Chemical Abstracts Service (CAS) number 1250973-55-7, represents a unique structural motif that combines a brominated aromatic ring with a cyclopropyl substituent and a nitro group. Such structural features make it a valuable intermediate in the synthesis of more complex molecules, particularly in the development of novel therapeutic agents.

The bromine atom at the para position relative to the nitro group in 2-Bromo-N-cyclopropyl-4-nitroaniline introduces reactivity that is highly useful in further functionalization. This reactivity can be exploited through various cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, which are pivotal in constructing biaryl frameworks found in many biologically active compounds. The presence of the nitro group further enhances its utility, as nitro compounds are well-documented for their role in drug discovery due to their ability to serve as precursors for amine derivatives through reduction.

Recent advancements in synthetic methodologies have highlighted the importance of N-cyclopropyl substituted aromatic compounds. The cyclopropyl group, being a small and rigid three-membered ring, can influence the electronic properties and steric environment of the aromatic system. This influence is particularly relevant in medicinal chemistry, where subtle modifications can lead to significant changes in pharmacokinetic and pharmacodynamic profiles. The combination of these structural elements in 2-Bromo-N-cyclopropyl-4-nitroaniline makes it an intriguing candidate for further exploration.

In the context of drug development, 2-Bromo-N-cyclopropyl-4-nitroaniline has been explored as a precursor for various bioactive molecules. For instance, its transformation into more complex scaffolds has been investigated for potential applications in oncology and anti-inflammatory therapies. The bromine atom allows for facile introduction of other functional groups, while the nitro group can be reduced to an amine, providing multiple pathways for derivatization. These attributes make it a versatile building block in synthetic chemistry.

The synthesis of 2-Bromo-N-cyclopropyl-4-nitroaniline typically involves multi-step processes that require careful optimization to ensure high yield and purity. Common synthetic routes include bromination of an appropriate precursor followed by nitration and subsequent introduction of the cyclopropyl moiety. Advances in catalytic systems and green chemistry principles have enabled more efficient and environmentally benign synthetic strategies, which are increasingly important in industrial-scale production.

From a computational chemistry perspective, the electronic properties of 2-Bromo-N-cyclopropyl-4-nitroaniline have been studied to understand its reactivity and potential interactions with biological targets. Density Functional Theory (DFT) calculations have revealed insights into how the bromine and nitro groups modulate the aromatic system's electron density distribution. These studies not only aid in rationalizing experimental observations but also guide the design of more effective derivatives.

The pharmaceutical industry has shown interest in 2-Bromo-N-cyclopropyl-4-nitroaniline due to its potential as an intermediate for kinase inhibitors and other enzyme-targeted drugs. Kinases play crucial roles in cellular signaling pathways, making them attractive therapeutic targets for diseases such as cancer and autoimmune disorders. By incorporating structural motifs similar to those found in known kinase inhibitors, researchers aim to develop novel compounds with improved efficacy and selectivity.

In addition to its applications in drug discovery, 2-Bromo-N-cyclopropyl-4-nitroaniline has found utility in materials science. Its ability to participate in cross-coupling reactions makes it valuable for constructing organic semiconductors and conductive polymers. These materials are essential components in electronic devices such as organic light-emitting diodes (OLEDs) and solar cells. The versatility of this compound underscores its importance beyond traditional pharmaceutical applications.

The safety profile of 2-Bromo-N-cyclopropyl-4-nitroaniline is another critical consideration during its handling and use. While it is not classified as a hazardous substance under standard regulatory guidelines, appropriate precautions must be taken to prevent exposure due to its potential irritant properties. Standard laboratory practices, including the use of personal protective equipment (PPE) such as gloves, goggles, and lab coats, are recommended when working with this compound.

Future research directions involving 2-Bromo-N-cyclopropyl-4-nitroaniline may focus on exploring new synthetic pathways that enhance its accessibility and scalability. Additionally, investigating its biological activity through high-throughput screening could uncover unexpected therapeutic potentials. Collaborative efforts between academic researchers and industry scientists will be crucial in translating these findings into tangible benefits for society.

• 24402-71-9(Benzenamine, 2,6-dibromo-N,N-dimethyl-4-nitro-)
• 64230-23-5(N,N-Dimethyl 2-bromo-4-nitroaniline)
• 6911-88-2(2-Bromo-N-methyl-4-nitroaniline)
• 108485-08-1(N-Ethyl 2-Bromo-4-nitroaniline)
• 1150271-18-3(N,N-Diethyl 2-Bromo-4-nitroaniline)
• 179898-71-6(Benzenamine, 2-bromo-N-(2-methyl-2-propenyl)-5-nitro-)
• 1157464-28-2(2-Bromo-4-nitro-N-propylaniline)
• 887351-39-5(N-Cyclopropyl 4-bromo-2-nitroaniline)
• 1396554-46-3(3-Bromo-N-cyclopropyl-2-nitrobenzenamine)
• 952664-76-5(2-Bromo-N-(tert-butyl)-4-nitroaniline)