Production Method 1

96-73-1

Reaction Conditions

1.1 Reagents: Chlorosulfonic acid ;  16 h, rt → 120 °C

Reference

Preparation of N-hydroxyamides omega-substituted with tricyclic groups as histone deacetylase inhibitors, their preparation and use in pharmaceutical formulations

, World Intellectual Property Organization, , ,

Production Method 2

96-73-1

Reaction Conditions

Reference

Preparation of sulfonic acids by sulfonation of hydrocarbons with sulfur trioxide

, Japan, , ,

Production Method 3

96-73-1

Reaction Conditions

Reference

Preparation of 2-chloro-5-nitro- and 4-chloro-3-nitrobenzenesulfonyl chloride

, European Patent Organization, , ,

Production Method 4

96-73-1

Reaction Conditions

1.1 Reagents: Sulfur trioxide ;  50 °C; 6 h, 110 - 115 °C
1.2 Reagents: Sodium chloride Solvents: Water ;  115 °C → 50 °C

Reference

Technological improvements for synthesizing 4,4'-diaminodiphenylamine-2-sulfonic acid

Hu, Zhangyun, Ranliao Gongye, 2002, 39(4), 32-34

Production Method 5

96-73-1

Reaction Conditions

1.1 Reagents: Fuming sulfuric acid ;  0 °C → 110 °C; overnight, 110 °C; 110 °C → rt
1.2 Reagents: Sodium chloride Solvents: Water ;  5 °C

Reference

Development of benzenesulfonamide derivatives as potent glutathione transferase omega-1 inhibitors

Xie, Yiyue; Tummala, Padmaja ; Oakley, Aaron J.; Deora, Girdhar Singh ; Nakano, Yuji; et al, Journal of Medicinal Chemistry, 2020, 63(6), 2894-2914

Production Method 6

96-73-1

Reaction Conditions

1.1 Reagents: Fuming sulfuric acid ;  6 h, 110 - 115 °C; cooled
1.2 Reagents: Sodium chloride Solvents: Water ;  0.5 h, 5 - 10 °C

Reference

Synthesis and evaluation of novel monosubstituted sulfonylurea derivatives as antituberculosis agents

Pan, Li; Jiang, Ying; Liu, Zhen; Liu, Xing-Hai; Liu, Zhuo; et al, European Journal of Medicinal Chemistry, 2012, 50, 18-26

Production Method 7

96-73-1

Reaction Conditions

1.1 Reagents: Chlorosulfonic acid ;  18 h, rt → 120 °C

Reference

Thromboxane receptor antagonists

, World Intellectual Property Organization, , ,

Production Method 8

96-73-1

Reaction Conditions

1.1 Reagents: Chlorosulfonic acid ;  18 h, 120 °C

Reference

Preparation of substituted phenylsulfonylurea compounds as thromboxane receptor binding agents useful for treating proliferative disorders and viral infections

, World Intellectual Property Organization, , ,

Production Method 9

96-73-1

Reaction Conditions

1.1 Reagents: Sulfur trioxide ,  Ammonium sulfate
1.2 Reagents: Water

Reference

Sulfonation of 2-chloronitrobenzene, 4-chloronitrobenzene, and 2-methylnitrobenzene

, Federal Republic of Germany, , ,

Production Method 10

96-73-1

Reaction Conditions

Reference

Sulfonation of substituted nitrobenzenes

, France, , ,

Production Method 11

96-73-1

Reaction Conditions

Reference

4-Morpholinoaniline-3-sulfonamides

, Japan, , ,

2-Chloro-5-nitrobenzenesulfonic acid Preparation Products

• 2-Chloro-5-nitrobenzenesulfonic acid (96-73-1)

• 1. Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study?
  Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander Orlov Catal. Sci. Technol., 2015,5, 2059-2064
• 2. Fate of nitrogen-15 in the subsequent growing season of greenhouse tomato plants (Lycopersicon esculentum Mill) as influenced by alternate partial root-zone irrigation
  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400
• 3. Excess electrons in lithium–ethylamine solutions—density, electrical conductivity and EPR studies
  Phys. Chem. Chem. Phys., 1999,1, 3561-3565
• 4. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 5. Fe3O4 nanoclusters highly dispersed on a porous graphene support as an additive for improving the hydrogen storage properties of LiBH4?
  Guang Xu,Wei Zhang,Ying Zhang,Xiaoxia Zhao,Ping Wen,Di Ma RSC Adv., 2018,8, 19353-19361

Introduction to 2-Chloro-5-nitrobenzenesulfonic acid (CAS No. 96-73-1)

2-Chloro-5-nitrobenzenesulfonic acid, with the chemical formula C?H?ClNO?S, is a significant compound in the field of organic chemistry and pharmaceutical research. This compound, identified by its CAS number 96-73-1, has garnered considerable attention due to its versatile applications in synthesis and its role as an intermediate in the development of various pharmaceuticals and agrochemicals. The presence of both chloro and nitro substituents on the benzene ring imparts unique reactivity, making it a valuable building block for further chemical transformations.

The structural features of 2-Chloro-5-nitrobenzenesulfonic acid contribute to its utility in multiple domains. The sulfonic acid group (-SO?H) enhances its solubility in polar solvents, facilitating its use in aqueous-based reactions and processes. This property is particularly advantageous in pharmaceutical synthesis, where solubility can influence drug bioavailability and formulation. Additionally, the chloro and nitro groups introduce electrophilic centers, enabling nucleophilic substitution reactions that are pivotal in constructing more complex molecular architectures.

In recent years, research has highlighted the role of 2-Chloro-5-nitrobenzenesulfonic acid in the development of novel therapeutic agents. Its derivatives have been explored as potential intermediates in the synthesis of antimicrobial and anti-inflammatory compounds. For instance, studies have demonstrated its utility in generating sulfonamide derivatives, which are known for their biological activity. The nitro group can be reduced to an amine, providing a pathway to introduce amine functionalities that are crucial for drug design.

The pharmaceutical industry has also leveraged 2-Chloro-5-nitrobenzenesulfonic acid for the synthesis of kinase inhibitors. Kinases are enzymes involved in numerous cellular processes, and their inhibition is a key strategy in cancer therapy. Researchers have utilized the compound’s reactive sites to develop molecules that can selectively inhibit specific kinases, thereby reducing side effects and improving therapeutic outcomes. The chloro group serves as a handle for further functionalization, allowing chemists to fine-tune the properties of these inhibitors.

Beyond pharmaceuticals, 2-Chloro-5-nitrobenzenesulfonic acid finds applications in materials science and polymer chemistry. Its ability to participate in sulfonation reactions makes it useful for modifying polymer backbones, enhancing properties such as thermal stability and water resistance. These modifications are particularly relevant in the development of advanced materials for industrial applications.

The synthesis of 2-Chloro-5-nitrobenzenesulfonic acid typically involves nitration and chlorination of benzene derivatives followed by sulfonation. Advances in synthetic methodologies have improved the efficiency and scalability of these processes, making the compound more accessible for research and industrial use. Modern techniques, such as catalytic sulfonation and green chemistry approaches, have been employed to minimize waste and reduce environmental impact.

In academic research, 2-Chloro-5-nitrobenzenesulfonic acid has been used as a model compound to study reaction mechanisms and develop new catalytic systems. Its well-defined structure allows researchers to probe electronic effects and steric influences on reaction outcomes. Such studies contribute to a deeper understanding of organic chemistry principles and inform the design of more efficient synthetic routes.

The future prospects for 2-Chloro-5-nitrobenzenesulfonic acid are promising, with ongoing research exploring its potential in drug discovery and material science. Innovations in computational chemistry are enabling virtual screening of its derivatives for novel bioactivities, accelerating the identification of lead compounds. Additionally, sustainable chemistry initiatives aim to optimize its synthesis using renewable resources and energy-efficient methods.

In conclusion, 2-Chloro-5-nitrobenzenesulfonic acid (CAS No. 96-73-1) is a multifaceted compound with significant applications across multiple scientific disciplines. Its structural features make it a valuable intermediate for pharmaceuticals, agrochemicals, and advanced materials. As research continues to uncover new uses and refine synthetic methodologies, this compound is poised to remain a cornerstone of chemical innovation.

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