2297-01-0

Basic information

• Product Name: methyl 2-sulfonamido-4-nitrobenzoate
• Synonyms: methyl 2-sulfonamido-4-nitrobenzoate
• CAS NO: 2297-01-0
• Molecular Weight: 260.227
• Mol File: 2297-01-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 2-sulfonamido-4-nitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-sulfonamido-4-nitrobenzoate(2297-01-0)
• EPA Substance Registry System: methyl 2-sulfonamido-4-nitrobenzoate(2297-01-0)

Safety Data

• Hazardous Substances Data: 2297-01-0(Hazardous Substances Data)

Usage

Description

Methyl 2-sulfonamido-4-nitrobenzoate, also known as Methyl 4-nitroanthranilate, is a chemical compound belonging to the sulfonamide class. It features a molecular formula of C8H8N2O6S and is characterized by the presence of a sulfonamide group, a nitro group, and a methyl ester group attached to a benzene ring. methyl 2-sulfonamido-4-nitrobenzoate is primarily utilized as a building block in the synthesis of pharmaceuticals and agrochemicals, and has been investigated for its potential antimicrobial and anti-inflammatory properties.

Uses

Used in Pharmaceutical Industry:
Methyl 2-sulfonamido-4-nitrobenzoate serves as a key building block in the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a versatile component in the development of new drugs with potential applications in treating a range of diseases.
Used in Agrochemical Industry:
In the agrochemical sector, methyl 2-sulfonamido-4-nitrobenzoate is employed as a precursor in the production of agrochemicals. Its incorporation into these products can contribute to the development of more effective and targeted pest control solutions.
Used in Antimicrobial Applications:
Methyl 2-sulfonamido-4-nitrobenzoate has been studied for its antimicrobial properties, making it a potential candidate for use in applications aimed at combating microbial infections. Its ability to inhibit the growth of certain microorganisms could be harnessed in the development of new antimicrobial agents.
Used in Anti-inflammatory Applications:
methyl 2-sulfonamido-4-nitrobenzoate's anti-inflammatory potential has also been explored, suggesting that it could be utilized in the development of treatments for inflammatory conditions. Its capacity to reduce inflammation may be beneficial in managing a variety of health issues related to excessive inflammation.

Upstream product

• 67-56-1 methanol 
• 22952-24-5 6-nitrosaccharin 
• 99-55-8 2-methyl-5-nitroaniline 
• 121-02-8 2-methyl-5-nitrobenzene-1-sulfonyl chloride 
• 6269-91-6 4-nitrotoluene-2-sulfonamide 
• 22952-26-7 2-carboxy-5-nitrobenzenesulfonic acid 
• 90110-01-3 2-chlorosulfonyl-4-nitro-benzoyl chloride 
• 154712-47-7 2-methoxycarbonyl-5-nitrobenzenesulfonyl chloride 

Downstream Products

• 2297-06-5 methyl 4-amino2-(aminosulfonyl)-benzoate 
• 89795-77-7 2-sulfonamido-4-nitrobenzoic acid 

Relevant articles and documents

Synthesis of saccharin-glycoconjugates targeting carbonic anhydrase using a one-pot cyclization/deprotection strategy

Carbonic anhydrase IX (CA IX) has been identified as a biomarker and drug target for several malignant tumors due to its role in cancer cell growth and proliferation. Simple cyclic sulfonamides, like saccharin (SAC), have shown up to a 60-fold selectivity towards CA IX over other ubiquitous CA isoforms, with greater selectivity obtained applying the “tail-approach” to derivatize SAC with a methylene triazole linker that connected to a “tail” beta glucoside. These modifications of SAC led to an increased selectivity of more than 1000-fold towards CA IX, whereas clinically available CA inhibitors show little to no isoform selectivity. As part of our interest in the development of new CA inhibitors, we found the existing synthetic protocol, which relies on a N-tert-butyl saccharin intermediate, to be problematic in the final deprotection steps. We therefore describe an alternative approach to the synthesis of these compounds featuring a gentle “one pot” deprotection/cyclization as the final synthetic step, and report new galactosyl and glucosyl conjugates with low to mid nM inhibition of CA IX.

Research on Controllable Degradation of Novel Sulfonylurea Herbicides in Acidic and Alkaline Soils

The degradation issue of sulfonylurea (SU) has become one of the biggest challenges that hamper the development and application of this class of herbicides, especially in the alkaline soils of northern China. On the basis of the previous discovery that some substituents on the fifth position of the benzene ring in Chlorsulfuron could hasten its degradation rate, apparently in acidic soil, this work on Metsulfuron-methyl showed more convincing results. Two novel compounds (I-1 and I-2) were designed and synthesized, and they still retained potent herbicidal activity in tests against both dicotyledons and monocotyledons. The half-lives of degradation (DT50) assay revealed that I-1 showed an accelerated degradation rate in acidic soil (pH 5.59). Moreover, we delighted to find that the degradation rate of I-1 was 9-10-fold faster than that of Metsulfuron-methyl and Chlorsulfuron when in alkaline soil (pH 8.46), which has more practical value. This research suggests that a modified structure that has potent herbicidal activity as well as accelerated degradation rate could be realized and this approach may provide a way to improve the residue problem of SUs in farmlands with alkaline soil.