4171-83-9

Usage

Uses

Used in Pharmaceutical Research:
2-Nitrophenyl Phenyl Sulfide is used as a research compound for the development of non-nucleoside reverse transcriptase inhibitors (NNRTIs) of HIV-1. These inhibitors play a crucial role in the treatment of HIV/AIDS by targeting the reverse transcriptase enzyme, which is essential for the replication of the virus. The study of 2-Nitrophenyl Phenyl Sulfide helps researchers understand the structure-activity relationship and design more effective NNRTIs to combat HIV-1.
Used in Chemical Synthesis:
2-Nitrophenyl Phenyl Sulfide can also be used as an intermediate in the synthesis of various organic compounds and pharmaceuticals. Its unique structure allows for further chemical modifications, making it a valuable building block for the development of new drugs and other chemical products.
Used in Analytical Chemistry:
In analytical chemistry, 2-Nitrophenyl Phenyl Sulfide can be employed as a reagent or a reference compound for the development and optimization of analytical methods. Its distinct spectral properties and reactivity can be utilized for the detection, quantification, and separation of various compounds in complex samples.

Synthesis Reference(s)

Synthetic Communications, 16, p. 1335, 1986 DOI: 10.1080/00397918608056380

InChI:InChI=1/C12H9NO2S/c14-13(15)11-8-4-5-9-12(11)16-10-6-2-1-3-7-10/h1-9H

Upstream product

• 64-17-5 ethanol 
• 577-19-5 2-nitrophenyl bromide 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 88-73-3 2-Chloronitrobenzene 
• 52599-08-3 o-Nitrobenzoldiazophenylsulfid 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 31515-43-2 1-nitro-2-(phenylsulfonyl)benzene 
• 54615-61-1 S-(2-nitrophenyl)-S-phenylsulfilimine 
• 609-73-4 o-nitroiodobenzene 
• 1493-27-2 ortho-nitrofluorobenzene 
• 3111-52-2 potassium thiophenolate 
• 882-33-7 diphenyldisulfane 
• 4875-10-9 o-nitrothiophenol 

Downstream Products

• 1637-16-7 10-ethyl-phenothiazine 
• 88958-92-3 4-(1-Benzenesulfonyl-3-methyl-but-2-enyl)-1-nitro-2-phenylsulfanyl-benzene 
• 6764-13-2 2-aminodiphenyl sulfide hydrochloride 
• 90158-92-2 N,N'-Bis-(2-phenylsulfanyl-phenyl)-diazene N-oxide 
• 141691-24-9 2-Phenylthiophenylhydroxylamine 
• 108-98-5 thiophenol 
• 88-74-4 2-nitro-aniline 
• 88-75-5 2-hydroxynitrobenzene 
• 14665-52-2 2,2'-dinitrodiphenyl sulfone 
• 34418-84-3 1-nitro-2-((3-nitrophenyl)sulfonyl)benzene 
• 57864-63-8 1-nitro-2-((4-nitrophenyl)sulfonyl)benzene 
• 18739-95-2 1-nitro-2-(phenylsulfinyl)benzene 
• 21387-93-9 4-nitrophenyl 2-nitrophenyl sulfide 
• 232604-74-9 4-Oxo-8-phenylsulfanyl-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis of N-allyl and N-acyl-2-vinylindoline

Heating a mixture of (2R*,3R*)- and (2R*,3S*)-2- [(1S*)-1-iodoethyl]-3,5-dimethyl-1-[(2-nitrophenyl) sulfonyl]indolines with N-isopropylpiperidine in xylene resulted in (2S*,3R*)-3,5- dimethyl-1-[(2-nitrophenyl) sulfonyl]-2-vinylindoline. The latter reacted with thiophenol to afford (2S*,3R*)-3,5-dimethyl-2-vinylindoline, whose reaction with allyl halides or acetyl bromide gave rise to N-allyl-, N-propenyl-, or N-acetyl derivatives. Nitration of 1-acetyl-3,5-dimethyl-2- vinylindoline yielded ortho-nitro derivative.

2-Sulfoximidoyl acetic acids from multicomponent petasis reactions and their use as building blocks in syntheses of sulfoximine benzodiazepine analogues

Upon application of a multicomponent Petasis reaction, a broad range of NH-sulfoximines and boronic acids react with glyoxalic acid to afford the corresponding 2-substituted acetic acids with N-bound sulfoximidoyl groups. The protocol features excellent y

Synthesis of thioethers, arenes and arylated benzoxazoles by transformation of the C(aryl)-C bond of aryl alcohols

Transformation of aryl alcohols into high-value functionalized aromatic compounds by selective cleavage and functionalization of the C(aryl)-C(OH) bond is of crucial importance, but very challenging by far. Herein, for the first time, we report a novel and versatile strategy for activation and functionalization of C(aryl)-C(OH) bonds by the cooperation of oxygenation and decarboxylative functionalization. A diverse range of aryl alcohol substrates were employed as arylation reagents via the cleavage of C(aryl)-C(OH) bonds and effectively converted into corresponding thioether, arene, and arylated benzoxazole products in excellent yields, in a Cu based catalytic system using O2 as the oxidant. This study offers a new way for aryl alcohol conversion and potentially offers a new opportunity to produce high-value functionalized aromatics from renewable feedstocks such as lignin which features abundant C(aryl)-C(OH) bonds in its linkages.

Intermediacy of Copper(I) under Oxidative Conditions in the Aerobic Copper-Catalyzed Decarboxylative Thiolation of Benzoic Acids

An experimental mechanistic study of the aerobic copper-catalyzed decarboxylative thiolation of benzoic acids with arenethiols is reported. For the model reaction, the findings support the corresponding disulfide (PhSSPh) of the arenethiol (PhSH) as the active thiolating source under reaction conditions. Synthesis and reactivity studies along with kinetic measurements support the chemical and kinetic competence of catalytically active well-defined Cu complexes: (phen)CuI(O2CC6H4-o-NO2) (2), [(phen)CuI(μ-SC6H5)]2 (3), (phen)CuI(C6H4-o-NO2) (4), and (phen)CuII(O2CC6H4-o-NO2)2 (5) (phen = 1,10-phenanthroline). The presence of an induction period in the stoichiometric reaction of the copper(II) complex (phen)CuII(O2CC6H4-o-NO2)2 (5) with PhSSPh and the absence of an induction period in the analogous stoichiometric reaction of the copper(I) complex (phen)CuI(O2CC6H4-o-NO2) (2) suggest that a copper(I) carboxylate is a more likely intermediate than a copper(II) carboxylate. The observation of in situ reduction of CuII to CuI further supports CuI as the primary active catalytic species, and spectroscopic studies also indicate the catalyst resting state to be a CuI species. The catalytic reaction exhibits a first-order dependence on [CuI] and [2-nitrobenzoic acid] and a zero-order dependence on [PhSSPh] and p(O2), suggestive of turnover-limiting decarboxylation of a copper(I) carboxylate. Oxygen was found to promote the essential oxidative cleavage of the copper(I) thiolate intermediate [(phen)CuI(μ-SC6H5)]2 (3) to regenerate a catalytically active [(phen)CuII] (Cuox) species with concomitant formation of PhSSPh. On the basis of these findings, a reaction pathway is proposed for the C-S coupling reaction that includes the key CuI-based intermediates (phen)CuI(O2CC6H4-o-NO2) (2) and (phen)CuI(C6H4-o-NO2) (4). The pathway accounts for the role of O2 in generating the active thiolating source, PhSSPh, as well as enabling catalytic turnover of in situ generated [(phen)CuI(μ-SC6H5)]2 (3).

An Iodide-Mediated Transition-Metal-Free Strategy towards Unsymmetrical Diaryl Sulfides via Arylhydrazines and Thiols

A mild, scalable iodine-mediated oxidative cross-coupling reaction of arylhydrazines and thiols for construction of thioethers (sulfides) in the absence of any transition metals or photocatalysts is disclosed. A variety of unsymmetrical diaryl sulfides with broad substrate scope both on thiols and hydrazines were synthesized in high yields in water at room temperature. Furthermore, to demonstrate the utility of the protocol, the above C-S bond formation was applied in the synthesis of the key structure of vortioxetine as an antidepressant drug. The gram-scale outcome also added to the potential utility of this protocol.

Homoleptic and heteroleptic Zn(ii) selone catalysts for thioetherification of aryl halides without scrubbing oxygen

Five new mononuclear tetra-coordinated zinc(ii) selones, [Zn(L1)2Cl2] (1), [Zn(L1)2Br2] (2), [{Zn(L2)4}{BF4}2] (3), [{Zn(L2)4}{ClO4}2] (4), and [Zn(L2)2Br2] (5), have been isolated from a one-pot reaction between the corresponding zinc(ii) salt and selone ligand, 1-methyl 3-naphthylmethylimidazoline-2-selone (L1) or 1-isopropyl 3-methylimidazoline-2-selone (L2). All these complexes were characterized by CHN analysis, FT-IR, NMR studies, and single-crystal X-ray crystallography techniques. The Zn(ii) center in 1-5 exhibits a distorted tetrahedral geometry. Besides, 1-5 were employed as catalysts in the thioetherification of aryl halides. The first zinc(ii) catalyst-mediated thioetherification of aryl halides without scrubbing oxygen was demonstrated. Catalysts 1-5 are highly active towards the cross-coupling reaction between aryl halides and thiophenols. The catalytic ability of 1-5 was explored in THF, toluene, and CH3CN solvents with different bases such as K2CO3, Cs2CO3, and NaOtBu. Interestingly, the zinc(ii) center attached to two selone ligands is much more catalytically active than that attached to four selone ligands.

Highly active mesoionic chalcogenone zinc(II) derivatives for C-S cross-coupling reactions

The first mesoionic heavier chalcogenones, L1-L3 [L1 = 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-selone; L2 = 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-thione; L3 = 1-(benzyl)-2-3(methyl)-4-phenyltriazolin-5-selone], were isolated and characterised. Density functional theory was used to obtain insights into the σ donor and π accepting nature of mesoionic chalcogenones. Using these new ligands, a series of the first zinc(ii) mesoionic chalcogenone complexes were isolated. Three mono nuclear zinc(ii) chalcogenone complexes, [(L1)Zn(Cl)2(HOMe)] (1), [(L2)Zn(Cl)2(HOMe)] (3) and [(L2)Zn(Br)2(HOMe)] (4), and two dinuclear zinc complexes, [(L1)Zn(Br)(μ2-Br)]2 (2) and [(L3)Zn(Br)(μ2-Br)]2 (5), containing mesoionic thione and selone ligands were synthesized and characterised. These new complexes 1-5 represent the first structurally characterized mesoionic chalcogenone supported metal derivatives. Furthermore, all zinc complexes were characterized by thermogravimetric analysis and UV-vis spectroscopy. The solid-state structures of all zinc complexes were determined by single-crystal X-ray diffraction. The catalytic activities of the zinc(ii) complexes in thioetherification reactions were investigated without scrubbing of oxygen. The scope of the catalytic reactions was explored with a wide range of thiophenols and aryl halides. The diaryl thioethers were obtained in very good yield under mild conditions. The present protocol furnishes a synthetic route for the C-S cross-coupling of thiophenols and aryl halides without scrubbing oxygen and moisture.

Cerium catalyst promoted C-S cross-coupling: Synthesis of thioethers, dapsone and RN-18 precursors

In this work, we present a novel, efficient and green methodology for the synthesis of thioethers by the C-S cross-coupling reaction with the assistance of [Ce(l-Pro)2]2Ox as a heterogeneous catalyst in good to excellent yields. A scale-up of the protocol was explored using an unpublished methodology for the synthesis of a dapsone-precursor, which proved to be very effective over a short time. The catalyst [Ce(l-Pro)2]2Ox was recovered and it was shown to be effective for five more reaction cycles.

Anionic Bismuth(III) chloride cluster with diselenide countercations: Application in C-S cross coupling reactions

The first weakly coordinating anion (WCA) with reactive p-block cation (rPBC) type of [(Bi4Cl16)4-{(LSeSeL)2+}2], L = 1,3-bis(2-benzhydryl-4,6-dimethylphenyl)-1H-imidazole-2(3H), ion pair is reported. The tetranuclear anionic bismuth(III) cluster shows a new type of ladder structure with two different types of Bi(III) coordination modes. In the solid state structure, the tetranuclear bismuth(III) cluster is sandwiched by two diselenide cations through hydrogen bonding interactions. Besides, this ion pair has been efficaciously employed as catalyst in C-S cross-coupling reactions under optimized reaction condition. This ion pair depicted a wide range of substrate scope with different thiols and aryl halides.

Visible-light-promoted organic dye-catalyzed sulfidation and phosphorylation of arylhydrazines toward aromatic sulfides and diarylphosphoryl hydrazides

Visible-light-promoted sulfidation and phosphorylation of arylhydrazines for the synthesis of aromatic sulfides and diarylphosphoryl hydrazides were developed using the organic dyes rose bengal and Na2-eosin Y as photocatalysts, respectively. This strategy offers an efficient and mild transition-metal-free synthetic protocol for the formation of C-S and N-P bonds from arylhydrazines.