27826-42-2

Usage

Physical state

Pale yellow solid

Molecular weight

199.24 g/mol

Common uses

Organic synthesis, intermediate in production of pharmaceuticals, dyes, and agricultural chemicals, reagent in preparation of various organic compounds

Potential properties

Antibacterial, antifungal

Applications

Building block in materials science and nanotechnology

Handling precautions

Toxic and harmful if ingested or inhaled

Upstream product

• 45797-13-5 4-nitrophenylthiolate 
• 107-08-4 1-iodo-propane 
• 71-23-8 propan-1-ol 
• 2137-92-0 4-nitrophenyl thiocyanate 
• 107-03-9 1-thiopropane 
• 100-00-5 4-chlorobenzonitrile 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 106-94-5 propyl bromide 
• 636-98-6 p-nitrobenzene iodide 
• 21865-11-2 1-nitro-4-(propylsulfinyl)benzene 
• 350-46-9 4-Fluoronitrobenzene 
• 100-01-6 4-nitro-aniline 
• 629-19-6 Dipropyl disulfide 
• 1849-36-1 para-nitrobenzenethiol 

Downstream Products

• 22133-40-0 4-aminophenyl propyl sulphide 
• 189639-05-2 2-[(2-hydroxy-ethyl)-(4-propylsulfanyl-phenyl)-amino]-ethanol 
• 189639-08-5 bis(2-chloroethyl)(4-propylthiophenyl)amine 

Relevant academic research and scientific papers

The Dependence of Ionic Liquid Solvent Effects on the Nucleophilic Heteroatom in SNAr Reactions. Highlighting the Potential for Control of Selectivity

Nucleophilic aromatic substitution (SNAr) reactions of 1-fluoro-4-nitrobenzene using similar nitrogen and sulfur nucleophiles were studied through extensive kinetic analysis in mixtures containing ionic liquids. The interactions of the ionic li

Electrophilic Chlorine from Chlorosulfonium Salts: A Highly Chemoselective Reduction of Sulfoxides

Herein, we describe a selective late-stage deoxygenation of sulfoxides based on a novel application of chlorosulfonium salts and demonstrate a new process using these species generated in situ from sulfoxides as the source of electrophilic chlorine. The use of highly nucleophilic 1,3,5-trimethoxybenzene (TMB) as the reducing agent is described for the first time and applied in the deoxygenation of simple and functionalized sulfoxides. The method is easy to handle, economic, suitable for gram-scale operations, and readily applied for poly-functionalized molecules, as demonstrated with more than 45 examples, including commercial medicines and analogues. We also report the results of competition experiments that define the more reactive sulfoxide and we present a mechanistic proposal based on substrate and product observations.

Ascorbic Acid Promoted Metal-Free Synthesis of Aryl Sulfides with Anilines Nitrosated in Situ by tert -Butyl Nitrite

A mild, metal-free synthesis of aryl sulfides has been disclosed. Aryl diazonium ion was generated by the in situ nitrosation of aniline, and it was reduced by ascorbic acid (vitamin C) to form aryl radical, which underwent a thiolation with disulfide to yield aryl sulfide. The reaction proceeded smoothly without heating or irradiation. This strategy was also expanded to the synthesis of aryl selenides.

Enantioselective nitrene transfer to sulfides catalyzed by a chiral iron complex

Iron works: Enantioselective nitrene transfer to sulfide was accomplished by a chiral iron(III)/PyBOX catalyst (see scheme). Various sulfimides were thus obtained in high enantioselectivities and yields. Applications of this protocol to the syntheses of enantioenriched sulfoximines and an epoxide were also demonstrated. Copyright

Microwave efficient S-arylation of thiols with aryl iodides using supported metal nanoparticles

An efficient and green microwave-assisted heterogeneous S-arylation protocol, reported for the first time, provided excellent coupling conversions and selectivities in minutes of reaction using Fe (homocoupling) and Cu (cross-coupling) supported metal nanoparticles.

Sulfite-promoted one-pot synthesis of sulfides by reaction of aryl disulfides with alkyl halides

A sodium dithionite, sodium thiosulfate and rongalite promoted one-pot synthesis of aryl alkyl sulfides at room temperature has been developed. The reactions of a range of disulfides with alkyl halides proceeded smoothly in the presence of rongalite. Possible reaction pathways are discussed and the effects of these sulfites on disulfides are investigated. The important features of this protocol are metal-free, strong-base-free, and mild reaction conditions, operational simplicity, short reaction times and high yields of products. Georg Thieme Verlag Stuttgart.

One-pot synthesis of sulfides by reaction of disulfides with alkyl halides in the presence of sodium dithionite

Sodium dithionite-promoted synthesis of unsymmetrical diorganyl sulfides by a reaction of diaryl disulfides with alkyl halides at r.t. has been developed. The advantages offered by this method are operational simplicity, a faster reaction, neutral and mild reaction conditions, and moderate to good yields of products.

Selective trifluorination of alkyl aryl sulfides using IF5

In the reaction of IF5 with alkyl aryl sulfides in heptane under reflux conditions, the arylthio group migrated once and three fluorine atoms were selectively introduced on the alkyl chain. In order to find the reason why the reaction stopped at the trifluorination step, we examined the oxidation potentials of the starting material, a reaction intermediate, and the product, and the time course of the reactions. Graphical Abstract.

Synthesis and in vitro antifungal activity of 4-substituted phenylguanidinium salts

A series of 4-substituted phenylguanidinium derivatives was synthesized and its antimicrobial activity was evaluated in vitro against eight potentially pathogenic strains of fungi.

Relative Nucleophilicities of Aryldisulphide and Thiolate Ions in Dimethylacetamide Estimated from their Reaction Rates with Alkyl Halides

The relative rates of nucleophilic substitution (SN2) of alkyl halides by aromatic thiolates ArS- and aryldisulphide ions ArS2- have been studied in dimethylacetamide by UV-visible spectrophotometry for Ar = 4-nitrophenyl (1), 2-nitrophenyl (2), and 8-quinolyl (3).Rate constants are relative to the rate constants for benzenethiolate ions (4), studied as reference.With Ar = (1), the reaction rate for disulphide ions is ten times higher than that for monosulphide ions stabilized by the elevated delocalization of their charge.With Ar = (2) and (3), the reactivity of disulphide ions is higher than that of the corresponding thiolates.Our study is consistent with the uncomplicated introduction of a disulphide bond into various substrates from aryldisulphide ions stabilized in aprotic dipolar media.