73322-01-7

Basic information

• Product Name: 1-NITRO-4-(2-PYRIDYLTHIO)BENZENE
• Synonyms: 1-NITRO-4-(2-PYRIDYLTHIO)BENZENE
• CAS NO: 73322-01-7
• Molecular Formula: C₁₁H₈N₂O₂S
• Molecular Weight: 232.26
• Product Categories: Pyridines
• Mol File: 73322-01-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-NITRO-4-(2-PYRIDYLTHIO)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-NITRO-4-(2-PYRIDYLTHIO)BENZENE(73322-01-7)
• EPA Substance Registry System: 1-NITRO-4-(2-PYRIDYLTHIO)BENZENE(73322-01-7)

Safety Data

• Hazardous Substances Data: 73322-01-7(Hazardous Substances Data)

Usage

1-Nitro-4-(2-Pyridylthio)benzene Properties

A compound consisting of 11 carbon atoms, 8 hydrogen atoms, 2 nitrogen atoms, 2 oxygen atoms, and 1 sulfur atom.
2. Nitrobenzene derivative
A compound derived from nitrobenzene by modifying its structure, in this case, by attaching a pyridylthio group at the 4-position.
3. Pyridylthio group attachment at the 4-position
A pyridylthio group (a pyridine ring with a sulfur atom attached) is connected to the benzene ring at the 4th carbon position.
4. Organic synthesis utility
The compound is commonly used in organic synthesis, serving as a building block for the preparation of various organic compounds.
5. Potential applications in pharmaceutical and agrochemical industries
Due to its ability to form diverse chemical bonds and structural motifs, the compound has potential uses in the development of pharmaceutical and agrochemical products.
6. Reagent and precursor uses
The compound can be used as a reagent in chemical reactions and as a precursor for the synthesis of various functional materials.
7. Health and environmental hazards
1-Nitro-4-(2-Pyridylthio)benzene may pose health and environmental risks, so it should be handled with care and proper safety precautions.

Upstream product

• 2637-34-5 pyridine-2-thione 
• 100-00-5 4-chlorobenzonitrile 
• 13327-62-3 2-mercaptopyridine sodium salt 
• 107263-95-6 N-fluoropyridinium triflate 
• 1849-36-1 para-nitrobenzenethiol 
• 107264-09-5 1-fluoro-pyridinium tetrafluoroborate 
• 79236-86-5 2-mercaptopyridine potassium salt 
• 2637-34-5 2-Sulfanylpyridine 
• 350-46-9 4-Fluoronitrobenzene 
• 636-98-6 p-nitrobenzene iodide 
• 586-78-7 para-nitrophenyl bromide 
• 109-04-6 2-bromo-pyridine 
• 2937-05-5 4-nitrobenzenesulfonohydrazide 
• 197958-29-5 pyridin-2-ylboronic acid 

Downstream Products

• 70991-08-1 4-(pyridine-2-ylthio)-aniline 
• 69770-62-3 2-(4-nitrobenzenesulfonyl)-pyridine 
• 2127-03-9 2,2'-dipyridyldisulphide 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 91933-69-6 (4-nitro-phenyl)-[2]pyridyl disulfide 
• 497850-82-5 7-{4-[2-(butoxy)ethoxy]phenyl}-1-propyl-N-{4-[(2-pyridyl)sulfanyl]phenyl}-2,3-dihydro-1H-1-benzazepine-4-carboxamide 
• 147696-59-1 4-(pyridine-2-sulfonyl)-aniline 
• 1279130-14-1 4-nitrophenyl 2-pyridyl sulfoxide 

Relevant articles and documents

Dimsyl Anion Enables Visible-Light-Promoted Charge Transfer in Cross-Coupling Reactions of Aryl Halides

A methodology is reported for visible-light-promoted synthesis of unsymmetrical chalcogenides enabled by dimsyl anion in the absence of transition-metals or photoredox catalysts. The cross-coupling reaction between aryl halides and diaryl dichalcogenides proceeds with electron-rich, electron-poor, and heteroaromatic moieties. Mechanistic investigations using UV-Vis spectroscopy, time-dependent density functional theory (TD-DFT) calculations, and control reactions suggest that dimsyl anion forms an electron-donor-acceptor (EDA) complex capable of absorbing blue light, leading to a charge transfer responsible for generation of aryl radicals from aryl halides. This previously unreported mechanistic pathway may be applied to other light-induced transformations performed in DMSO in the presence of bases and aryl halides.

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.

Palladium-catalyzed heteroaryl thioethers synthesis overcoming palladium dithiolate resting states inertness: Practical road to sulfones and NH-sulfoximines

We provide efficient synthetic access to heteroaryl sulfones in two-steps using a simple palladium–1,1′-bis[(diphenyl)phosphanyl]ferrocene catalyst to form in high yields variously functionalized heteroaromatic thioethers. Pyridinyl-containing substrates can be subsequently selectively oxidized into sulfones and NH-sulfoximines by using very mild oxidation conditions with a high functional group tolerance. In the palladium-catalyzed C–S coupling of heteroaromatic thiols, reactivity limitation is attached with electron-deficient thiols. We show that this limitation can be resolved by the successful use of 2-bromoheteroarenes in the C–S coupling. We established herein that this choice of heteroaryl electrophilic reagent in palladium-catalyzed C–S bond formation allows overcoming palladium dithiolate out-of-cycle resting state inertness. This was illustrated in the stoichiometric reactivity study of the palladium dithiolate formed from 4-trifluoromethylbenzen-1-thiol –isolated and characterized by multinuclear NMR and XRD– with both 2-chloropyridine and 2-bromopyridine.

Transition metal-free, chemoselective arylation of thioamides yielding aryl thioimidates or N-aryl thioamides

Reactions of secondary thioamides with diaryliodonium salts under basic, transition metal-free conditions resulted in chemoselective S-arylation to provide aryl thioimidates in good to excellent yields. Equimolar amounts of thioamide, base and diaryliodonium salt were sufficient to obtain a diverse selection of products within short reaction times. Reactions with thiolactams delivered N-arylated thioamides in good yield at room temperature.

Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: An electrophile-nucleophile dual activation by [Omim]Br for the reaction

A facile aromatic nucleophilic substitution (SNAr) reaction in recyclable [Omim]Br under relatively mild conditions has been described. An electrophile-nucleophile dual activation by [Omim]Br is also discovered based on control experiments, 1H NMR and IR spectroscopies. This chemistry provides an efficient and metal-free approach for the generation of Caryl-X (XS, N, O) bonds, many of which are significant synthetic intermediates or drugs, making this methodology attractive to both synthetic and medicinal chemistry.

Nickel-catalyzed C-S bond formation: Synthesis of aryl sulfides from arylsulfonyl hydrazides and boronic acids

A practical nickel-catalysed approach has been developed for the C-S bond formation through the cross-coupling of arylsulfonyl hydrazides and aryl boronic acids. The report employs arylsulfonyl hydrazide as an aryl thiol equivalent and offers a mild and eco-safe synthesis of unsymmetrical thioethers in good to excellent yields in air. The scope and versatility of the method has been successfully demonstrated with 22 examples.

Synthesis of heteroaryl containing sulfides via enaminone ligand assisted, copper-catalyzed C-S coupling reactions of heteroaryl thiols and aryl halides

The C-S cross coupling reactions between electron deficient heteroaryl thiols and aryl halides have been smoothly performed to provide various heteroaryl containing sulfides in the presence of copper catalyst and enaminone ligand. the Partner Organisations 2014.

Convenient MW-assisted synthesis of unsymmetrical sulfides using sulfonyl hydrazides as aryl thiol surrogate

An efficient synthesis of unsymmetrical sulfides has been achieved via the cross-coupling reaction of aryl/het-aryl/benzyl halides with stable and easily workable sulfonyl hydrazides as thiol substitutes by means of [DBU][HOAc] and CuI under microwave irr

KF/clinoptilolite: An efficient promoter for the synthesis of thioethers

Potassium fluoride impregnated on natural zeolite as a new solid base system effectively catalyzes the coupling of thiophenols with electron-deficient fluoro-, chloro- and bromo-arenes in DMSO. This versatile and efficient solid base has been demonstrated to afford the corresponding desired products in good to excellent yields. This procedure provides a convenient, efficient and practical method for the preparation of diaryl thioethers.

The [Cu]-catalyzed SNAR reactions: Direct amination of electron deficient aryl halides with sodium azide and the synthesis of arylthioethers under Cu(II) - Ascorbate redox system

A one pot [Cu]-promoted SNAr reaction of electron-deficient halobenzenes with sodium azide and the reduction of the intermediate aryl azides under the same Cu(II)-ascorbate redox conditions leading to anilines has been documented. Control experiments revealed that both ascorbate and proline play important role in the reaction path way. Further, the use of this catalytic Cu(II)-ascorbate redox system has been explored for the synthesis of arylthioethers.