Production Method 1

7499-73-2

90767-01-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Ethanol ,  Tetrahydrofuran ,  Water ;  rt → 80 °C; 8 h, 80 °C

Reference

Solution synthesis of N = 8 armchair graphene nanoribbons with high charge carrier mobility

Yao, Xuelin; Zhang, Heng; Kong, Fanmiao; Okuno, Masanari; Horton, Peter N.; et al, ChemRxiv, 2023, 1, 1-6

4-Bromo-2-nitronaphthalen-1-amine Raw materials

• Acetamide,N-(4-bromo-2-nitro-1-naphthalenyl)-

4-Bromo-2-nitronaphthalen-1-amine Preparation Products

• 4-Bromo-2-nitronaphthalen-1-amine (90767-01-4)

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  Partha Laskar,Christine Dufès Nanoscale Adv., 2021,3, 6007-6026
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Chemical Profile of 4-Bromo-2-nitronaphthalen-1-amine (CAS No. 90767-01-4)

4-Bromo-2-nitronaphthalen-1-amine, identified by its Chemical Abstracts Service (CAS) number 90767-01-4, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical and chemical research. This naphthalene derivative features both bromine and nitro substituents, which make it a versatile intermediate in the synthesis of more complex molecules. The unique structural attributes of this compound contribute to its utility in various chemical transformations, particularly in the development of novel therapeutic agents.

The molecular structure of 4-Bromo-2-nitronaphthalen-1-amine consists of a naphthalene core substituted at the 1-position with an amine group, at the 2-position with a nitro group, and at the 4-position with a bromine atom. This arrangement imparts distinct reactivity patterns, making it a valuable building block for medicinal chemists and synthetic organic chemists. The presence of both electron-withdrawing (nitro) and electron-donating (amine) groups allows for diverse functionalization strategies, enabling the construction of intricate molecular architectures.

In recent years, 4-Bromo-2-nitronaphthalen-1-amine has been explored as a precursor in the synthesis of biologically active compounds. Its incorporation into drug-like molecules has shown promise in several therapeutic areas, including oncology, inflammation, and central nervous system disorders. The bromine substituent, in particular, facilitates cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings, which are pivotal in constructing carbon-carbon and carbon-nitrogen bonds essential for drug design.

One of the most compelling applications of 4-Bromo-2-nitronaphthalen-1-amine is in the development of kinase inhibitors. Kinases are enzymes that play a crucial role in cell signaling pathways, and their dysregulation is often associated with diseases such as cancer. By leveraging the reactivity of this compound, researchers have synthesized novel inhibitors that target specific kinases with high selectivity. For instance, derivatives of 4-Bromo-2-nitronaphthalen-1-amine have been reported to exhibit inhibitory activity against tyrosine kinases, which are key players in tumor growth and metastasis.

Moreover, the nitro group in 4-Bromo-2-nitronaphthalen-1-amine can be reduced to an amine or hydroxyl group under appropriate conditions, providing further opportunities for structural diversification. This redox-active nature makes it particularly useful in generating compounds with different pharmacological profiles. Recent studies have demonstrated its use in designing molecules with anti-inflammatory properties by modulating cytokine production and inhibiting inflammatory pathways.

The pharmaceutical industry has also shown interest in 4-Bromo-2-nitronaphthalen-1-amine for its potential in central nervous system (CNS) drug development. Naphthalene derivatives have been explored for their ability to cross the blood-brain barrier, making them attractive candidates for treating neurological disorders. Researchers have utilized 4-Bromo-2-nitronaphthalen-1-amine as a scaffold to develop compounds that interact with neurotransmitter systems involved in mood regulation, pain perception, and cognitive function.

Synthetic methodologies involving 4-Bromo-2-nitronaphthalen-1-amine have been refined to achieve high yields and purity levels, ensuring its suitability for industrial-scale production. Advances in catalytic systems and green chemistry principles have further enhanced the efficiency of its synthesis, reducing waste and energy consumption. These improvements align with the growing emphasis on sustainable practices in pharmaceutical manufacturing.

From a research perspective, 4-Bromo-2-nitronaphthalen-1-amine continues to be a subject of investigation due to its broad applicability. Computational studies have been conducted to predict its interactions with biological targets, aiding in the rational design of new derivatives. High-throughput screening techniques have also been employed to identify lead compounds derived from this scaffold, streamlining the drug discovery process.

The versatility of 4-Bromo-2-nitronaphthalen-1-amine extends beyond pharmaceutical applications. It has found utility in materials science as well, particularly in the synthesis of organic semiconductors and luminescent materials. The ability to modify its structure allows researchers to fine-tune its electronic properties, making it suitable for optoelectronic devices such as organic light-emitting diodes (OLEDs) and photovoltaic cells.

In conclusion,4-Bromo - 2 - nitro naphthalen - 1 - amine (CAS No. 90767 - 01 - 4) is a multifaceted compound with significant potential across multiple domains of chemistry and biology. Its unique structural features enable diverse synthetic strategies, making it an invaluable intermediate for drug development and materials science. As research progresses, 4 - bromo - 2 - nitro naphthalen - 1 - amine will likely continue to play a pivotal role in advancing scientific understanding and technological innovation.

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