5455-59-4

Basic information

• Product Name: 2-Nitrobenzenesulfonamide
• Synonyms: O-NITROBENZENESULFONAMIDE;O-NITROBENZENESULFONYLAMIDE;2-Nitrobenzenesulfonamide, 98+%;2-Nitrobenzenesulphonamide,98+%;2-NITROPHENYLSULFAMIDE;2-NITROBENZENESULFONYLAMINE;2-Nitrobenzolsulfonamid;2-Nitrobenzenesulfonamide,96%
• CAS NO: 5455-59-4
• Molecular Formula: C₆H₆N₂O₄S
• Molecular Weight: 202.19
• Product Categories: Intermediates of Dyes and Pigments;Organic Building Blocks;Sulfonamides/Sulfinamides;Sulfur Compounds
• Mol File: 5455-59-4.mol
• Article Data: 17

Chemical Properties

• Melting Point: 189-194 °C
• Boiling Point: 418.8 °C at 760 mmHg
• Flash Point: 207.1 °C
• Appearance: /solid
• Density: 1.505 (estimate)
• Vapor Pressure: 3.18E-07mmHg at 25°C
• Refractive Index: 1.6490 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO, Methanol (Slightly, Heated, Sonicated)
• PKA: 9.24±0.60(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 2214215
• CAS DataBase Reference: 2-Nitrobenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitrobenzenesulfonamide(5455-59-4)
• EPA Substance Registry System: 2-Nitrobenzenesulfonamide(5455-59-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-22-37/39
• WGK Germany: 3
• Hazardous Substances Data: 5455-59-4(Hazardous Substances Data)

Usage

Description

2-Nitrobenzenesulfonamide is a carbonic anhydrase inhibitor, characterized by its yellow to light brown crystalline powder appearance. It is a chemical compound with significant applications in various industries due to its unique properties.

Uses

Used in Pharmaceutical Industry:
2-Nitrobenzenesulfonamide is used as a pharmaceutical agent for its carbonic anhydrase inhibitory properties. It plays a crucial role in the treatment of conditions that involve the regulation of acid-base balance in the body, such as glaucoma, certain types of epilepsy, and altitude sickness. By inhibiting carbonic anhydrase, it helps in reducing intraocular pressure and preventing the overproduction of carbon dioxide, which can lead to these medical conditions.
Used in Chemical Research:
In the field of chemical research, 2-Nitrobenzenesulfonamide serves as an important compound for studying the mechanisms of carbonic anhydrase enzymes and their role in various biological processes. Its use in research contributes to the development of new drugs and therapies targeting carbonic anhydrase-related diseases.
Used in Environmental Applications:
2-Nitrobenzenesulfonamide can also be utilized in environmental applications, such as water treatment and pollution control. Its ability to inhibit carbonic anhydrase can be leveraged to control the growth of certain microorganisms and algae that contribute to water pollution. This application helps in maintaining the ecological balance and ensuring the availability of clean water resources.

InChI:InChI=1/C6H6N2O4S/c7-13(11,12)6-4-2-1-3-5(6)8(9)10/h1-4H,(H2,7,11,12)

Upstream product

• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 22057-44-9 1-(benzylsulfanyl)-2-nitrobenzene 
• 1155-00-6 bis(2-nitrophenyl)disulfide 
• 88-73-3 2-Chloronitrobenzene 
• 863033-39-0 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[1-(2-nitro-benzenesulfonyl)-6-oxo-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 62-53-3 aniline 

Downstream Products

• 91818-65-4 acetoacetyl-(2-nitro-benzenesulfonyl)-amine 
• 198572-71-3 N-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamide 
• 5454-97-7 2-nitro-N-phenylbenzenesulfonamide 
• 155564-92-4 Ni(C₁₅H₂₆N₆O₄S)Cl₂ 
• 1087136-86-4 C₂₉H₂₆N₂O₅S 
• 1099752-34-7 (-)-2-nitro-N-{(1S)-1-[(trityloxy)methyl]prop-2-enyl}benzenesulfonamide 
• 1087137-05-0 2-nitro-N-[(2E)-4-(trityloxy)but-2-enyl]benzenesulfonamide 
• 51144-95-7 1-((2-nitrophenyl)sulfonyl)-1H-pyrrole 
• 1206455-31-3 C₁₈H₁₆N₄O₄S 
• 1206455-33-5 C₁₈H₁₈N₆O₄S 
• 1206455-34-6 C₁₈H₁₄Br₂N₄O₄S 
• 1206455-32-4 dimethyl 6,6'-(2-nitrophenylsulfonylazanediyl)bis(methylene)dinicotinate 
• 1265139-79-4 N,N'-(6,6'-(2-nitrophenylsulfonylazanediyl)bis(methylene)bis(pyridine-6,2-diyl))bis(2,2-dimethylpropanamide) 
• 1206455-35-7 C₂₂H₂₂N₆O₆S 

Relevant articles and documents

Conformational properties of ortho-nitrobenzenesulfonamide in gas and crystalline phases. Intra- and intermolecular hydrogen bond

A combined gas-phase electron diffraction and quantum chemical (B3LYP/6-311+G, B3LYP/cc-pvtz, MP2/cc-pvtz) study of molecular structure of 2-nitrobenzenesulfonamide (2-NBSA) was carried out. Quantum chemical calculations showed that 2-NBSA has four confor

Rational Design, synthesis and biological evaluation of novel triazole derivatives as potent and selective PRMT5 inhibitors with antitumor activity

Protein arginine methyltransferase 5 (PRMT5) is responsible for the mono-methylation and symmetric dimethylation of arginine, and its expression level and methyl transferring activity have been demonstrated to have a close relationship with tumorigenesis, development and poor clinical outcomes of human cancers. Two PRMT5 small molecule inhibitors (GSK3326595 and JNJ-64619178) have been put forward into clinical trials. Here, we describe the design, synthesis and biological evaluation of a series of novel, potent and selective PRMT5 inhibitors with antiproliferative activity against Z-138 mantle cell lymphoma cell line. Among them, compound C_4 exhibited the highest potency with enzymatic and cellular level IC50 values of 0.72 and 2.6 μM, respectively, and displayed more than 270-fold selectivity toward PRMT5 over several other isoenzymes (PRMT1, PRMT4 and PRMT6). Besides, C_4 demonstrated obvious cell apoptotic effect while reduced the cellular symmetric arginine dimethylation levels of SmD3 protein. The potency, small size, and synthetic accessibility of this compound class provide promising hit scaffold for medicinal chemists to further explore this series of PRMT5 inhibitors.

Synthesis of (-)-Cytisine Using a 6- endo aza-Michael Addition

An asymmetric synthesis of (-)-cytisine has been achieved. The piperidine C-ring was formed using a stereodivergent intramolecular 6-endo aza-Michael addition. The B-ring was established by intramolecular pyridine N-alkylation. The absolute stereochemistry was established by an Evans acyl oxazolidinone enolate alkylation reaction that proceeded with an unexpected stereochemical outcome due to participation of the pyridine nitrogen lone pair.