92323-58-5

Upstream product

• 629-27-6 1-Iodooctane 
• 13113-79-6 sodium 4-nitrobenzenethiolate 
• 16156-52-8 n-octyl methanesulfonate 
• 3028-88-4 trioctyl phosphite 
• 2137-92-0 4-nitrophenyl thiocyanate 
• 111-88-6 Octanethiol 
• 100-00-5 4-chlorobenzonitrile 
• 111-87-5 octanol 
• 1849-36-1 para-nitrobenzenethiol 
• 586-78-7 para-nitrophenyl bromide 
• 111-83-1 1-bromo-octane 
• 636-98-6 p-nitrobenzene iodide 

Downstream Products

• 92324-60-2 1-nitro-4-(octylsulfonyl)benzene 
• 59960-76-8 4-(octylthio)benzenamine 

Relevant academic research and scientific papers

One-Pot Copper-Catalysed Thioetherification of Aryl Halides Using Alcohols and Lawesson's Reagent in Diglyme

A new protocol for the thioetherification of structurally varied alcohols with aryl halides using Lawesson's reagent, catalysed by copper(I) iodide, and using diglyme as a safe solvent was developed. Using this method, the reactions of aryl halides proceeded efficiently, and the desired sulfides were obtained in high to excellent yields. The method uses alcohols as starting materials, which is a significant advantage over methods that start from thiols. Alcohols are widely commercially available in a much greater structural diversity than thiols, and they are also nontoxic and not foul-smelling. A reaction mechanism was proposed. A copper-catalysed method for the thioetherification of alcohols with aryl halides using Lawesson's reagent was developed.

Synthesis and characterization of magnetic copper ferrite nanoparticles and their catalytic performance in one-pot odorless carbon-sulfur bond formation reactions

In this article, we have introduced catalytic application of copper ferrite nanoparticles (CuFe2O4) for one-pot odorless production of aryl alkyl thioethers using thiourea and alkyl bromides in wet polyethylene glycol as a green solvent. The catalyst was also successfully applied for one-pot synthesis of symmetrical diaryl trithiocarbonates via the reaction of sodium sulfide, carbon disulfide and aryl iodides under heterogeneous reaction condition. Magnetic copper ferrite nanoparticles were synthesized using iron (III) chloride and copper (II) chloride, and characterized using XRD, FT-IR, AAS, and TEM analysis. The catalyst was recycled using simple magnetic separation and reused for the five consecutive runs in the reaction of iodobenzene, thiourea and benzyl bromide without appreciable loss of activity.

A highly efficient palladium-catalyzed one-pot synthesis of unsymmetrical aryl alkyl thioethers under mild conditions in water

A palladium-catalyzed, one-pot synthesis of unsymmetrical aryl alkyl thioethers involving aryl halides (aryl bromides and chlorides), thiourea and alkyl bromides has been realized under mild conditions (room temperature to 50 °C) in water with polyoxyethanyl α-tocopheryl sebacate (PTS) as amphiphile. The PTS/water could be recycled in up to eight runs without an obvious change in its activity. Copyright

Efficient nickel/N-heterocyclic carbene catalyzed C-S cross-coupling

The cross-coupling reaction of aryl halides with aliphatic and aromatic thiols catalyzed by readily available Ni(OAc)2 with N-heterocyclic carbene (NHC) is reported. Ni(OAc)2/NHC catalyst showed good activities toward various aryl halides in C-S coupling reaction, even with aryl chlorides. Reactions occurred in excellent yields, broad scope, and high tolerance of functional groups.

Efficient nickel/N-heterocyclic carbene catalyzed C-S cross-coupling

The cross-coupling reaction of aryl halides with aliphatic and aromatic thiols catalyzed by readily available Ni(OAc)2 with N-heterocyclic carbene (NHC) is reported. Ni(OAc)2/NHC catalyst showed good activities toward various aryl halides in C-S coupling reaction, even with aryl chlorides. Reactions occurred in excellent yields, broad scope, and high tolerance of functional groups.

Facile preparation of aryl sulfides using palladium catalysis under mild conditions

A convenient method for C-S cross-coupling of aryl bromides with various thiols has been developed that involves the use of a 1,1′- bis(diphenylphosphino)ferrocene (DPPF)-ligated palladium complex with N,N-diisopropylethylamine (DIPEA) as the base. This coupling is tolerant of a wide range of functional groups, including hydroxy, amino, cyano, nitro, formyl, and carboxyl groups. Georg Thieme Verlag Stuttgart - New York.

One-pot synthesis of amine-substituted aryl sulfides and benzo[ b ]thiophene derivatives

A series of amine-substituted aryl sulfides have been synthesized from nitroaryl halides via a simple one-pot procedure involving metal-free C-S cross-coupling and in situ nitro group reduction. Various nitroaryl halides were reacted with thiols in recyclable poly(ethylene glycol) to afford the amine-substituted aryl sulfides in high yield. Additionally, the cross-coupling reactions of nitro- and aldehyde-substituted aryl halides with benzyl thiols under the same reaction conditions were demonstrated to afford benzothiazole and phenylbenzo[b]thiophene derivatives.

One-pot thioetherification of aryl halides using thiourea and alkyl bromides catalyzed by copper(I) iodide free from foul-smelling thiols in wet polyethylene glycol (PEG 200)

In this article, we have developed a new protocol for the thioarylation of structurally diverse alkyl bromides such as benzyl, cinnamyl, n-octyl, cyclohexyl, cyclopentyl, and tert-butyl bromides with aryl iodides, bromides and an activated chloride using thiourea catalyzed by copper(I) iodide in wet polyethylene glycol (PEG 200) as an eco-friendly medium in the presence of potassium carbonate at 80 and 100°C under an inert atmosphere. The process is free from foul-smelling thiols which makes this method more practical for the thioetherification of aryl halides. Another important feature of this method is the variety of alkyl bromides which are commercially available for the in situ generation of thiolate ions with respect to the existing protocols in which the less commercially available thiols are directly used for the preparation of arylthio ethers.

Design, synthesis and recognition properties of urea-type anion receptors in low polar media

The binding efficiency of simple receptors bearing two NH hydrogen-bond donor groups, of general formula PhCH2NH-Y-NHPh (Y = C=N-Ts, SO 2, CS, CO), towards selected anion guests has been evaluated in chloroform solution in order to assess the effect of the nature of different binding sites incorporated into the receptor scaffold. Experimental results together with molecular mechanics and quantum chemical calculations have revealed that the nature of the spacer Y induces important electronic effects and conformational changes that lead to different degrees of preorganisation of the NH binding groups. In addition, the synthesis and binding properties of new lipophilic urea-based receptors, having electron-withdrawing alkylsulfonyl substituents (SO2C8H17) and characterised by enhanced NH hydrogen-bond donor ability, is reported. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

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.