701-57-5

Usage

Uses

Used in Chemical Synthesis:
4-Nitrothioanisole is used as a chemical intermediate for the synthesis of 4-nitrothioanisole sulfoxide and methyl 4-nitrophenyl sulfoxide. These compounds have potential applications in various chemical and pharmaceutical industries.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 2575, 1983 DOI: 10.1016/S0040-4039(00)81985-1

InChI:InChI=1/C7H7NO2S/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3

Upstream product

• 67-56-1 methanol 
• 463-56-9 thiocyanic acid 
• 13118-32-6 p-nitrophenyldimethylsulphonium methylsulphate 
• 74-93-1 methylthiol 
• 100-00-5 4-chlorobenzonitrile 
• 2137-92-0 4-nitrophenyl thiocyanate 
• 66-27-3 Methyl methanesulfonate 
• 45797-13-5 4-nitrophenylthiolate 
• 676-88-0 dimethyl(methylthio)sulfonium tetrafluoroborate 
• 13113-79-6 sodium 4-nitrobenzenethiolate 
• 33613-52-4 dimethylphenyl sulfonium tetrafluoroborate 
• 73198-19-3 <(9-Oxobenzonorbornen-exo-2-yl)methyl>methyl(p-nitrophenyl)sulfonium tetrafluoroborate 
• 624-92-0 Dimethyldisulphide 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 940-12-5 p-nitrophenyl methyl sulfoxide 
• 2976-30-9 1-methanesulfonyl-4-nitrobenzene 
• 7205-88-1 1-[(chloromethyl)sulfanyl]-4-nitrobenzene 
• 713-66-6 4-nitrophenyl trichloromethylsulfide 
• 21229-92-5 4-methylthiophenylhydroxylamine 
• 861569-50-8 N,N'-bis-(4-methylsulfanyl-phenyl)-hydrazine 
• 104-96-1 4-methylsulfanylaniline 
• 13118-32-6 p-nitrophenyldimethylsulphonium methylsulphate 
• 72301-70-3 α-<2-Nitro-5-(methylthio)phenyl>acetonitrile 
• 89303-16-2 2-Benzenesulfonylmethyl-4-methylsulfanyl-1-nitro-benzene 
• 80723-54-2 C₉H₁₁O₃S^(1-)*C₇H₉N₂O₂S⁽¹⁺⁾ 
• 940-12-5 (S)-methyl 4-nitrophenyl sulfoxide 
• 940-12-5 (R)-methyl 4-nitrophenyl sulfoxide 
• 93222-06-1 methyl p-nitrophenyl sulfoxide 

Relevant academic research and scientific papers

A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction

In this work, we have explored how the confinement of the protic ionic liquid (IL) ethylammonium nitrate (EAN) inside toluene/benzyl-n-hexadecyldimethylammonium chloride (BHDC) reverse micelles (RMs) affects the Cl- nucleophilicity on the bimolecular nucleophilic substitution (SN2) reaction between this anion and dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate. To the best of our knowledge this is the first report where toluene/BHDC RMs use EAN as a polar component and it is used as a nanoreactor for carrying out kinetic experiments. Dynamic light scattering results reveal the formation of RMs containing the protic IL. The kinetic results show that upon confinement, EAN becomes a suitable solvent for the SN2 reaction while in homogeneous media it is a bad option. Entrapped in BHDC RMs, due to the strong hydrogen bond interactions, EAN behaves as an aprotic-like IL which cannot deactivate the nucleophilic power of Cl- and yet increases the substrate solubility. These facts show the versatility of this kind of organized system to alter the polar solvent entrapped and its influence on the reaction rate when it is used as a nanoreactor.

Evidence for the importance of polarizability in biomimetic catalysis involving cyclophane receptors

Cyclophanes 1-6 catalyze the nucleophilic dealkylation of a simple sulfonium compound by potassium iodide. The cation-π interaction is important in substrate binding, but the primarily electrostatic nature of this effect does not explain all observations concerning catalysis. As a series of substituents are placed on the cyclophane framework, a systematic variation in catalyst effectiveness is seen, such that more polarizable substituents produce more potent catalysts. This provides support for the notion that transition states are especially polarizable, and catalysis can be enhanced by maximizing London dispersion forces. The reactions studied here are very similar to the broad class of biological methylations mediated by S-adenosylmethionine, and the biological catalysts may use forces similar to those described here.

N-bromosuccinimide/HCl mediated reduction of sulfoxides to sulfides

An efficient reduction of sulfoxides to sulfides mediated by N-bromosuccinimide (NBS)/HCl system has been developed. This protocol shows good functional group compatibility as well as broad substrates scope with operational simplicity.

Synthesis of Aryl Methyl Sulfides from Arysulfonyl Chlorides with Dimethyl Carbonate as the Solvent and C1 Source

A new procedure for the synthesis of aryl methyl sulfides from dimethyl carbonate (DMC) and arylsulfonyl chlorides has been achieved. In this strategy, DMC plays a dual role as both, C1 building block and green solvent. Arylsulfonyl chlorides served as the sulfur precursors, and a variety of aryl methyl sulfides were obtained in moderate to excellent yields with good functional group tolerance. Additionally, alkylsulfonyl chloride and dibenzyl carbonate are proven to be suitable substrates as well.

Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer

A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.

t-BuOK-promoted methylthiolation of aryl fluorides with dimethyldisulfide under transition-metal-free and mild conditions

In the presence of potassium tert-butoxide (t-BuOK), the cross-coupling reaction between aryl fluorides and dimethyldisulfide was developed. A series of aryl methyl sulfides were obtained in moderate to good yields under transition-metal-free and mild conditions.

Copper-Catalyzed Methylthiolation of Aryl Iodides and Bromides with Dimethyl Disulfide in Water

An efficient route to aryl methyl sulfides through the copper-catalyzed coupling reaction of aryl iodides or bromides with dimethyl disulfide in water is described. Electron-donating and electron-withdrawing functional groups in the substrates were tolerated, and the corresponding products were obtained in moderate to good yields.

A Manganese N-Heterocyclic Carbene Catalyst for Reduction of Sulfoxides with Silanes

The first reduction of sulfoxides catalysed by a well-defined manganese complex is described. A variety of sulfoxides are reduced to the corresponding sulfides in high yields using phenylsilane, diphenylsilane, and the economically feasible 1,1,3,3-tetramethyldisiloxane (TMDS) as reducing agents in the presence of a Mn-NHC complex. The reaction is performed under air and without the need of any additive. The involvement of radicals in the catalytic reaction is probed by spin-trap experiments.

Enhancement of Benzothiazoles as Pteridine Reductase-1 Inhibitors for the Treatment of Trypanosomatidic Infections

2-Amino-benzo[d]thiazole was identified as a new scaffold for the development of improved pteridine reductase-1 (PTR1) inhibitors and anti-trypanosomatidic agents. Molecular docking and crystallography guided the design and synthesis of 42 new benzothiazoles. The compounds were assessed for Trypanosoma brucei and Leishmania major PTR1 inhibition and in vitro activity against T. brucei and amastigote Leishmania infantum. We identified several 2-amino-benzo[d]thiazoles with improved enzymatic activity (TbPTR1 IC50 = 0.35 μM; LmPTR1 IC50 = 1.9 μM) and low μM antiparasitic activity against T. brucei. The ten most active compounds against TbPTR1 were able to potentiate the antiparasitic activity of methotrexate when evaluated in combination against T. brucei, with a potentiating index between 1.2 and 2.7. The compound library was profiled for early ADME toxicity, and 2-amino-N-benzylbenzo[d]thiazole-6-carboxamide (4c) was finally identified as a novel potent, safe, and selective anti-trypanocydal agent (EC50 = 7.0 μM). Formulation of 4c with hydroxypropyl-β-cyclodextrin yielded good oral bioavailability, encouraging progression to in vivo studies.

Transition-Metal-Free Aryl-Heteroatom Bond Formation via C-S Bond Cleavage

Aryl-heteroatom bonds (C-Het) are almost ubiquitously present in chemical molecules. However, methods for diverse C-Het bond formations from a simple substrate are limited. Herein, we report a convenient and efficient C-S bond transformation of aryl sulfoniums to various C-Het bonds (C-O, C-S, C-Sn, C-Si, C-Se) in the absence of any transition-metal catalyst. These reactions proceeded in mild conditions with a wide substrate scope.