6655-77-2

Usage

Uses

Used in Organic Synthesis:
2-Nitrobenzenesulfonyl hydrazine is used as a reagent in organic synthesis for its ability to act as a powerful nucleophile, facilitating the conversion of ketones and aldehydes into hydrazones. This conversion is crucial for the synthesis of complex organic molecules and contributes to the advancement of chemical research and development.
Used in Pharmaceutical and Agrochemical Synthesis:
As a precursor in the synthesis of pharmaceuticals and agrochemicals, 2-Nitrobenzenesulfonyl hydrazine plays a significant role in the production of various medicinal compounds and agricultural products. Its involvement in these syntheses underscores its utility in creating substances that can have a broad impact on health and agriculture.
Safety Considerations:

InChI:InChI=1/C6H7N3O4S/c7-8-14(12,13)6-3-1-2-5(4-6)9(10)11/h1-4,8H,7H2

Upstream product

• 121-51-7 3-nitrobenzenesulphonyl chloride 

Downstream Products

• 6655-56-7 3-nitro-benzenesulfonic acid-(4-methoxy-benzylidenehydrazide) 
• 120167-62-6 3-nitro-benzenesulfonic acid salicylidenehydrazide 
• 6717-26-6 3-nitro-benzenesulfonic acid-(1-phenyl-ethylidenehydrazide) 
• 6647-84-3 3-nitro-N'-((3-nitrophenyl)sulfonyl)benzenesulfonohydrazide 
• 1554261-72-1 C₁₆H₁₇NO₃S 
• 1613246-83-5 (E)-N'-(1,3-diphenylbut-3-en-1-ylidene)-3-nitrobenzenesulfonohydrazide 
• 1613247-12-3 (R)-5-(iodomethyl)-1-((3-nitrophenyl)sulfonyl)-3,5-diphenyl-4,5-dihydro-1H-pyrazole 
• 1613247-67-8 5-(iodomethyl)-1-((3-nitrophenyl)sulfonyl)-3,5-diphenyl-4,5-dihydro-1H-pyrazole 
• 1338595-38-2 naphthalen-2-yl(3-nitrophenyl)sulfane 
• 121-89-1 3-Nitroacetophenone 

Relevant academic research and scientific papers

Electrochemical characterization of para- and meta-nitro substituents in aqueous media of new antichagasic pharmaceutical leaders

The electrochemical reduction mechanism of two isomers of position drug leaders against Chagas disease, p-nitrosulfonylhydrazine derivative (p-NSF), and m-nitrosulfonylhydrazine derivative (m-NSF), was investigated in aqueous media and in the absence of oxygen using voltammetric techniques. The main reduction process was attributed to the reduction of the nitro group (Epc (p-NSF) = ?0.58 V and Epc (m-NSF) = ?0.62 V), generating nitroso derivative in intermediate and higher values of pH and hydroxylamine in lower values of pH. Another reduction process in a less negative potential value was only observed for p-NSF and attributed to the generation of the nitro radical anion. The difference in the reduction potentials between both compounds and the presence of another reduction process for p-NSF was associated with the position of the nitro group, due to the distinct stabilization of the reduction intermediates by the aromatic ring. A catalytic response for the reduction process of the nitro anion radical was observed for p-NSF in the presence of oxygen, given that its magnitude of current increased when increasing the oxygen availability. Also, for m-NSF, this reduction process could be detected, even though it was not observed in the voltammograms in the absence of oxygen. This further confirmed the generation of the nitro radical anion, since it reacts with molecular oxygen and regenerates the initial nitro compound. The interaction with cysteine was also evaluated, which favored the reduction process towards the generation of the nitroso derivative due to adduct formation, destabilizing the reduction process regarding the nitro radical anion. Therefore, electrochemical experiments can evaluate how different isomers of position and other coupled functional groups affect the reduction of the nitro group and, consequently aid in the design of new classes of antichagasic pharmaceuticals, with improved stability of reactive intermediates that are often correlated with the degree of injury towards the parasite.

Synthesis, structural properties, enzyme inhibition and molecular docking studies of (Z)-N'-(1-allyl-2-oxoindolin-3-ylidene) methanesulfono-hydrazide and (Z)-N'-(1-allyl-2-oxoindolin-3-ylidene)-3-nitrobenzenesulfono-hydrazide

Isatin and its derivatives exhibit broad range of biological and pharmacological applications. Keeping in view the importance of isatin and its derivatives, herein we report two isatin based new sulfono-hydrazides 4 & 5, synthesized in high yields and characterized by spectroscopic techniques. Their structures are confirmed unequivocally using X-ray diffraction crystallography, which revealed the presence of P21/c (4) and P21/n (5) space groups and unit cells stabilized through noncovalent interactions. Further details about geometric and electronic properties of compounds 4 and 5 are obtained by quantum mechanical approach based on density functional theory (DFT). These compounds are also evaluated for in vitro urease enzyme inhibition potential against Bacillus pasteurii. Both compounds inhibited the urease activity in μM concentration, however, compound 4 with IC50 value of 15.26 ± 0.16 μM proved to be more potent than the standard thiourea having IC50 value of 21.25 ± 0.15 μM. The higher inhibition activity of compound 4 might be associated with its stronger interaction as observed by in silico molecular docking studies using MOE, which showed that compound 4 interacts more closely to the binding site of enzyme (4UBP) via Ni2+ ions coordination as compared to its counterpart.

TBAB-catalyzed 1,6-conjugate sulfonylation of paraquinone methides: A highly efficient approach to unsymmetrical gem-diarylmethyl sulfones in water ?

A highly efficient sulfonylation of para-quinone methides with sulfonyl hydrazines in water has been developed on the basis of the mode involving a tetrabutyl ammonium bromide (TBAB)-promoted sulfa-1,6-conjugated addition pathway. This reaction provides a green and sustainable method to synthesize various unsymmetrical diarylmethyl sulfones, showing good functional group tolerance, scalability, and regioselectivity. Further transformation of the resulting diarylmethyl sulfones provides an efficient route to some functionalized molecules.

Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides

Sulfonylated N-unsubstituted enamines were synthesized through a chain of chemical and electrochemical transformations via sulfonylation of vinyl azides. The disclosing of the N-unsubstituted enamines synthesis was based on a unique property of the azido group, which is its ability to eliminate the N2 molecule. Furthermore, a formal paradox is observed: A double bond reacts and a double bond is retained. Electrosynthesis proceeded in an undivided cell equipped with a graphite anode and a stainless steel cathode; NH4I was used as a supporting electrolyte.

Aromatic heterocyclic derivatives and application thereof to drugs

The invention discloses aromatic heterocyclic derivatives and an application thereof to drugs, and particularly relates to a kind of novel aromatic heterocyclic derivatives and pharmaceutical composition containing the compounds. The invention further rel

TBN-mediated regio- and stereoselective sulfonylation & oximation (oximosulfonylation) of alkynes with sulfonyl hydrazines in EtOH/H2O

An alkyne difunctionalization cascade reaction was developed to generate α-sulfonylethanone oximes under metal-free conditions. The reaction features environmentally benign EtOH/H2O as a solvent, a broad substrate scope and easily scaled up for gram-scale synthesis. The reaction mechanism was illustrated with UPLC, GC-MS and UPLC-tof/MS.

Copper-catalyzed: S -methylation of sulfonyl hydrazides with TBHP for the synthesis of methyl sulfones in water

A copper-catalyzed S-methylation of sulfonyl hydrazides with TBHP was efficiently developed, providing a variety of methyl sulfones with good to excellent yields. The reaction can be carried out in water smoothly without any ligand or additive under mild conditions and this catalyst-in-water can be recycled several times.

Base-mediated tandem sulfonylation and oximation of alkenes in water

A base-mediated bifunctionalization of alkenes for the synthesis of α-sulfonylethanone oximes was developed in water under metal-free conditions. This reaction features a wide substrate scope and facile starting materials to afford the desired products in high yields.

Catalyst-free thiolation of indoles with sulfonyl hydrazides for the synthesis of 3-sulfenylindoles in water

A catalyst-free thiolation of indoles with sulfonyl hydrazides was efficiently developed in water under mild conditions without any ligand or additive. The reaction provided a variety of 3-sulfenylindoles with good to excellent yields and the only by-products were nitrogen and water.

SAMDI Mass Spectrometry-Enabled High-Throughput Optimization of a Traceless Petasis Reaction

Development of the self-assembled monolayer/MALDI mass spectrometry (SAMDI) platform to enable a high-throughput optimization of a traceless Petasis reaction is described. More than 1800 unique reactions were conducted simultaneously on an array of self-assembled monolayers of alkanethiolates on gold to arrive at optimized conditions, which were then successfully transferred to the solution phase. The utility of this reaction was validated by the efficient synthesis of a variety of di- and trisubstituted allenes.