36331-57-4

Usage

Uses

Used in Organic Synthesis:
Phenylmethanesulfonohydrazide is used as a reagent for the selective reduction of carbonyl compounds to their corresponding alcohols, which is crucial in the synthesis of various organic compounds.
Used in Epoxy Resin Industry:
In the epoxy resin industry, phenylmethanesulfonohydrazide is used as a curing agent, which is essential for the hardening and setting of epoxy resins, enhancing their performance in various applications.
Used in Polymer Industry:
As a stabilizer for polymers, phenylmethanesulfonohydrazide helps to prevent degradation and improve the longevity and stability of polymeric materials.
Used in Food Industry:
Phenylmethanesulfonohydrazide is used as an inhibitor to prevent the formation of nitrosamines in certain food products, contributing to food safety and quality.
Used in Pharmaceutical Industry:
Phenylmethanesulfonohydrazide is researched for its potential applications in pharmaceuticals, indicating its possible use in the development of new drugs and therapeutic agents.
Used in Cosmetics Industry:
Its potential in cosmetics suggests that phenylmethanesulfonohydrazide could be utilized in the formulation of cosmetic products, potentially enhancing their efficacy and performance.

InChI:InChI=1/C7H10N2O2S/c8-9-12(10,11)6-7-4-2-1-3-5-7/h1-5,9H,6,8H2

Upstream product

• 329-98-6 phenylmethylsulphonyl fluoride 
• 1939-99-7 benzenesulfonyl chloride 

Downstream Products

• 4403-73-0 benzylsulfinic acid 
• 20474-37-7 benzylsulfonyl azide 
• 17075-10-4 phenylmethanesulfonyl bromide 
• 92256-05-8 2-Benzylsulfonyl-1-benzyl-hydrazin 
• 124790-91-6 C₁₀H₁₆N₂O₄S₂ 
• 75968-30-8 glyoxylic acid benzylsulfonylhydrazone 
• 1244620-36-7 C₂₀H₁₈N₂O₂S 
• 633291-96-0 3-(benzylsulfanyl)-1H-indole 
• 831-91-4 Benzyl phenyl sulfide 
• 13286-32-3 thiophosphoric acid S-benzyl ester O,O'-diethyl ester 
• 1402459-58-8 ethyl (Z)-3-(benzylsulfonyl)acrylate 

Relevant academic research and scientific papers

Dual Roles of Rongalite: Reductive Coupling Reaction to Construct Thiosulfonates Using Sulfonyl Hydrazides

A tunable and practical transformation of structurally diverse sulfonyl hydrazides into thiosulfonates in the presence of Rongalite (NaHSO 2·CH 2O) was developed. Transition-metal-free conditions, operational simplicity, and readily available reagents are the striking features of this protocol. It is the first example for the synthesis of thiosulfonates using sulfonyl hydrazides with the assistance of reductant. Additionally, the mechanistic studies revealed that this transformation probably undergoes via a reducing-coupling pathway.

Palladium-Catalyzed Asymmetric Hydrosulfonylation of 1,3-Dienes with Sulfonyl Hydrazides

A highly enantio- and regioselective hydrosulfonylation of 1,3-dienes with sulfonyl hydrazides has been realized by using a palladium catalyst containing a monodentate chiral spiro phosphoramidite ligand. The reaction provided an efficient approach to synthetically useful chiral allylic sulfones. Mechanistic studies suggest that the reaction proceeds through the formation of an allyl hydrazine intermediate and subsequent rearrangement to the chiral allylic sulfone product. The transformation of the allyl hydrazine intermediate to the product is the enantioselectivity-determining step.

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.

CuCl2-promoted decomposition of sulfonyl hydrazides for the synthesis of thiosulfonates

Sulfonyl hydrazides recently received much attention as reagents for the introduction of sulfur-containing functional groups into organic compounds, because both sulfonyl and sulfenyl sources could be generated by the oxidation and decomposition of the sulfonyl hydrazides, respectively. However, the transformations of sulfonyl hydrazides into thiosulfonates, which could be produced by the reaction between sulfonyl and sulfenyl sources, have been less investigated. In this manuscript, we describe CuCl2-promoted selective synthesis of thiosulfonates from sulfonyl hydrazides. A variety of thiosulfonates were produced in moderate to good yields. The mechanism involving radical intermediates such as sulfonyl radical and thiyl radical was proposed on the basis of the previously reported references and mechanistic investigations. In addition, quantum chemical simulations revealed that Cu-promoted decomposition of sulfonyl hydrazides is thermodynamically viable in the developed conditions.

An Alternative Metal-Free Aerobic Oxidative Cross-Dehydrogenative Coupling of Sulfonyl Hydrazides with Secondary Phosphine Oxides

An alternative metal-free, efficient and practical approach for the preparation of phosphinothioates is established via the aerobic oxidative cross-dehydrogenative coupling (CDC) of sulfonyl hydrazides with secondary phosphine oxides catalyzed by tetrabutylammonium iodide (TBAI) in the presence of atmospheric oxygen. The strategy provides an array of diverse phosphinothioates in good to excellent yields. Furthermore, two representative bioactive molecules are synthesized on up to gram scale by utilizing this method.

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.

Synthesis of 3,4-Dihydrobenzo[f]phthalazines via Iodine/tert-Butyl Hydroperoxide-Mediated Annulation Cascade of Yne-Allenones

An iodine (I2)/tert-butyl hydroperoxide (TBHP)-mediated annulation cascade between yne-allenones and sulfonyl hydrazides has been established, in which a wide set of dihydrobenzo[f]phthalazines were synthesized through one-pot, two-step strategy under metal-free conditions. The synthetic utility of these transformations leads to subsequent C?C and C?N bond-forming reactions to effectively build up functional aza-heterocycle with potential significance. (Figure presented.).

Structure-Guided Synthesis and Mechanistic Studies Reveal Sweetspots on Naphthyl Salicyl Hydrazone Scaffold as Non-Nucleosidic Competitive, Reversible Inhibitors of Human Ribonucleotide Reductase

Ribonucleotide reductase (RR), an established cancer target, is usually inhibited by antimetabolites, which display multiple cross-reactive effects. Recently, we discovered a naphthyl salicyl acyl hydrazone-based inhibitor (NSAH or E-3a) of human RR (hRR) binding at the catalytic site (C-site) and inhibiting hRR reversibly. We herein report the synthesis and biochemical characterization of 25 distinct analogs. We designed each analog through docking to the C-site of hRR based on our 2.7 ? X-ray crystal structure (PDB ID: 5TUS). Broad tolerance to minor structural variations preserving inhibitory potency is observed. E-3f (82% yield) displayed an in vitro IC50 of 5.3 ± 1.8 μM against hRR, making it the most potent in this series. Kinetic assays reveal that E-3a, E-3c, E-3t, and E-3w bind and inhibit hRR through a reversible and competitive mode. Target selectivity toward the R1 subunit of hRR is established, providing a novel way of inhibition of this crucial enzyme.

Diversity-Orientated Stereoselective Synthesis through Pd-Catalyzed Switchable Decarboxylative C?N/C?S Bond Formation in Allylic Surrogates

Switchable catalytic transformation of reactants can be a powerful approach towards diversity-orientated synthesis from easily available molecular synthons. Herein, an endogenous ligand-controlled, Pd-catalyzed allylic substitution allowing for either selective C?N or C?S bond formation using vinylethylene carbonates (VECs) and N-sulfonylhydrazones as coupling partners has been developed. This versatile methodology provides a facile, divergent route for the highly chemo- and stereoselective synthesis of functional allylic sulfones or sulfonohydrazides. The newly developed protocol features wide substrate scope (nearly 80 examples), broad functional group tolerance, and potential for the late-stage functionalization of bioactive compounds. The isolation and crystallographic analysis of a catalytically competent π-allyl Pd complex suggests that the pathway leading to the allylic products proceeds through a different manifold as previously proposed for the functionalization of VECs with nucleophiles.

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.