Production Method 1

619-24-9

118535-52-7

17420-30-3

6393-40-4

87331-46-2

Reaction Conditions

1.1 Reagents: tert-Butanol Solvents: Dimethylformamide
1.2 Solvents: Water

Reference

Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen: Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides

Makosza, Mieczyslaw; et al, Journal of Organic Chemistry, 1998, 63(15), 4878-4888

Production Method 2

17162-41-3

619-24-9

17420-30-3

6393-40-4

87331-46-2

Reaction Conditions

1.1 Reagents: tert-Butanol Solvents: Dimethylformamide
1.2 Solvents: Water

Reference

Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen: Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides

Makosza, Mieczyslaw; et al, Journal of Organic Chemistry, 1998, 63(15), 4878-4888

2-amino-5-nitro-benzonitrile Raw materials

• Benzenesulfenamide, 2,4,6-trichloro-
• 3-Nitrobenzonitrile
• Pyrrolidine, 1-[(aminothio)thioxomethyl]-

2-amino-5-nitro-benzonitrile Preparation Products

• 4-Amino-3-nitrobenzonitrile (6393-40-4)
• 2-amino-5-nitro-benzonitrile (17420-30-3)
• 2-amino-3-nitrobenzonitrile (87331-46-2)

• 1. Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation
  Matthew J. Gaunt,Jinquan Yu,Jonathan B. Spencer Chem. Commun., 2001, 1844-1845
• 2. Excellent mechanical performance and enhanced dielectric properties of OBC/SiO2 elastomeric nanocomposites: effect of dispersion of the SiO2 nanoparticles?
  Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei Yang RSC Adv., 2017,7, 46297-46305
• 3. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203
• 4. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
  Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139
• 5. Emerging enantiomeric resolution materials with homochiral nano-fabrications
  Ji-Ping Wei Nanoscale, 2015,7, 11815-11832

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Nitrobenzenes
• Solvents and Organic Chemicals Organic Compounds cyanides/Cyanides

Recent Advances in the Study of 2-Amino-5-nitro-benzonitrile (CAS: 17420-30-3) and Its Applications in Chemical Biology and Pharmaceutical Research

2-Amino-5-nitro-benzonitrile (CAS: 17420-30-3) is a nitro-substituted aromatic compound that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound serves as a key intermediate in the synthesis of various bioactive molecules, including heterocyclic compounds with potential therapeutic properties. Recent studies have explored its utility in drug discovery, particularly in the development of kinase inhibitors, antimicrobial agents, and fluorescent probes for biological imaging.

One of the most notable advancements in the study of 2-amino-5-nitro-benzonitrile is its role in the synthesis of novel kinase inhibitors. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibit potent inhibitory activity against cyclin-dependent kinases (CDKs), which are critical targets in cancer therapy. The researchers utilized structure-activity relationship (SAR) analysis to optimize the compound's scaffold, resulting in derivatives with improved selectivity and pharmacokinetic properties. These findings highlight the potential of 2-amino-5-nitro-benzonitrile as a versatile building block for anticancer drug development.

In addition to its applications in kinase inhibition, 2-amino-5-nitro-benzonitrile has been investigated for its antimicrobial properties. A recent study in Bioorganic & Medicinal Chemistry Letters reported the synthesis of a series of nitrobenzene derivatives, including 2-amino-5-nitro-benzonitrile, and evaluated their efficacy against multidrug-resistant bacterial strains. The results indicated that certain derivatives exhibited broad-spectrum antibacterial activity, with minimal cytotoxicity toward mammalian cells. This suggests that further optimization of these compounds could lead to the development of new antibiotics to address the growing threat of antimicrobial resistance.

Another exciting application of 2-amino-5-nitro-benzonitrile is in the field of fluorescent probes for biological imaging. Researchers have exploited the nitro group's electron-withdrawing properties to design probes with enhanced photostability and sensitivity. A 2022 study in Chemical Communications described the development of a nitrobenzene-based fluorescent probe for detecting reactive oxygen species (ROS) in live cells. The probe, derived from 2-amino-5-nitro-benzonitrile, demonstrated high selectivity for ROS and enabled real-time monitoring of oxidative stress in cellular models of neurodegenerative diseases. This innovation opens new avenues for studying oxidative stress-related pathologies and screening potential therapeutics.

Despite these promising developments, challenges remain in the practical application of 2-amino-5-nitro-benzonitrile and its derivatives. For instance, the nitro group's potential toxicity and metabolic instability necessitate careful optimization of the compound's pharmacokinetic profile. Recent efforts have focused on prodrug strategies and structural modifications to mitigate these issues. A 2023 review in Expert Opinion on Drug Discovery summarized these approaches and emphasized the importance of balancing efficacy and safety in the design of nitrobenzene-based therapeutics.

In conclusion, 2-amino-5-nitro-benzonitrile (CAS: 17420-30-3) continues to be a valuable scaffold in chemical biology and pharmaceutical research. Its diverse applications—from kinase inhibitors and antimicrobial agents to fluorescent probes—underscore its versatility and potential for innovation. Future research should focus on addressing the compound's limitations while exploring new therapeutic and diagnostic applications. As the field advances, 2-amino-5-nitro-benzonitrile is poised to play an increasingly important role in the development of next-generation pharmaceuticals and biomedical tools.

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