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Bis(2-nitrophenyl) sulfide is an organic compound that consists of two 2-nitrophenyl groups connected by a sulfur atom. It is a key intermediate in the synthesis of various chemical compounds and has unique chemical properties due to the presence of the sulfur atom and nitro groups.

22100-66-9

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22100-66-9 Usage

Uses

Used in Green Synthetic Preparation:
Bis(2-nitrophenyl) sulfide is used as a key intermediate in the green synthetic preparation of diaryl thioethers. This process involves a metal-free DBU-based ionic liquid-catalyzed coupling reaction of aryl halides with carbon disulfide, which is an environmentally friendly and efficient method for the synthesis of diaryl thioethers.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, bis(2-nitrophenyl) sulfide is used as a building block for the synthesis of various pharmaceutical compounds. Its unique chemical properties make it a valuable component in the development of new drugs and therapeutic agents.
Used in Chemical Research:
Bis(2-nitrophenyl) sulfide is also used in chemical research as a model compound to study the reactivity and properties of sulfur-containing organic compounds. This helps researchers to better understand the behavior of sulfur in various chemical reactions and develop new synthetic methods and applications.

Check Digit Verification of cas no

The CAS Registry Mumber 22100-66-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,1,0 and 0 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 22100-66:
(7*2)+(6*2)+(5*1)+(4*0)+(3*0)+(2*6)+(1*6)=49
49 % 10 = 9
So 22100-66-9 is a valid CAS Registry Number.

22100-66-9Relevant academic research and scientific papers

Ni-guanidine@MCM-41 NPs: a new catalyst for the synthesis of 4,4?-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ols) and symmetric di-aryl sulfides

Filian, Hossein,Ghorbani-Choghamarani, Arash,Tahanpesar, Elham

, p. 2673 - 2681 (2019/07/17)

In this work, the surface of mesoporous MCM-41 was modified with guanidine, and then, Nickel particles have become immobilized on its surface (Ni-guanidine@MCM-41NPs). This heterogeneous catalyst has been identified by various techniques including: low-angle X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma, thermal gravimetric analysis and N2 adsorption–desorption measurement isotherms, and its catalytic application was studied in the synthesis of 4,4?-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ol) derivatives and symmetric di-aryl sulfides. The prepared organometallic complex could be isolated, post-reaction, by simple filtration for several consecutive cycles without a notable change in its catalytic activity.

Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides

Li, Xing,Du, Jia,Zhang, Yongli,Chang, Honghong,Gao, Wenchao,Wei, Wenlong

, p. 3048 - 3055 (2019/03/21)

A highly chemoselective, efficient and nano-Pd catalyzed protocol for the rapid construction of sulfoxides and sulfones via the oxidation of symmetrical and unsymmetrical sulfides using H2O2 as an oxidant has been developed, respectively. The ready availability of starting materials, easy recovery and reutilization of the catalyst, wide substrate scope, and high yields make this protocol an attractive alternative. The process also involves the metal-free and microwave-promoted synthesis of symmetrical diarylsulfides, and FeCl3-mediated preparation of symmetrical diaryldisulfides through the reaction of arenediazonium tetrafluoroborates with Na2S·9H2O as a sulfur source. In addition, unsymmetrical sulfides were generated via the K2CO3-mediated reaction of arenediazonium tetrafluoroborates with symmetrical disulfides.

A novel heterogeneous nanocatalyst: 2-Methoxy-1-phenylethanone functionalized MCM-41 supported Cu(II) complex for C-S coupling of aryl halides with thiourea

Hajipour, Abdol R.,Fakhari, Farzaneh,Nabi Bidhendi, Gholamreza

, (2018/02/06)

An environmentally friendly copper-based catalyst supported on 2-Methoxy-1-phenylethanone functionalized MCM-41 was prepared and characterized by FT-IR, FE-SEM, TEM, XRD, EDX, BET and ICP techniques. The catalyst was applied for the C?S cross-coupling reaction of aryl halides with thiourea. Corresponding products were produced in good yields in aerobic conditions. The catalyst could be recovered and recycled for several times.

Histidine-functionalized chitosan-Cu(II) complex: A novel and green heterogeneous nanocatalyst for two and three component C-S coupling reactions

Hajipour, Abdol Reza,Hosseini, Seyed Mostafa,Jajarmi, Saeideh

, p. 7447 - 7452 (2017/08/01)

Using a fixing Cu2+ NP reaction on histidine modified chitosan, a novel applicable matrix was successfully prepared and investigated as a heterogeneous nanocatalyst for preparing diaryl sulfides and aryl benzyl thioethers. The Cu(ii)-his@CS nanocatalyst was characterized by FT-IR, CHN, XRD, FE-SEM, TEM, EDX, ICP-AES and TG analysis. This novel copper nanocatalyst was used for two and three component C-S coupling reactions of different aryl halides. The nanocatalyst showed high catalytic activity and reusability in both reactions.

Metal-free catalytic synthesis of diaryl thioethers under mild conditions

Cao, Xian-Ting,Zhang, Peng-Fei,Zheng, Hui

supporting information, p. 6762 - 6767 (2016/08/10)

A novel method to synthesize diaryl thioethers from aryl halides and carbon disulfide catalyzed by the 1,8-diazabicyclo[5,4,0]undec-7-enium acetate [DBUH][OAc] ionic liquid (IL) under solvent-free conditions has been developed. This metal-free catalytic system displayed high efficiency for coupling aryl halides with CS2 to deliver thioethers. Compared to the conventional methods, no metal catalyst was needed, instead of which the DBU-based ILs played the catalyst and solvent roles simultaneously. Some reactions were carried out under mild conditions (55 °C, 0.5 h), giving moderate to high yields. Moreover, compared with the rare reports, the reaction of the aryl chlorides and fluorides with CS2 could smoothly react in this catalytic system. The products were easily separated from the ILs which could be reused at least three times. The present method provides an efficient and environment-friendly catalytic approach to synthesize diaryl thioethers.

Microwave-assisted, metal- and solvent-free synthesis of diaryl thioethers from aryl halides and carbon disulfide in the presence of [DBUH]+[OAc]-

Zhou, Yongsheng

, p. 305 - 307 (2016/07/06)

A microwave-assisted direct coupling between aryl halides and carbon disulfide in ionic liquid [DBUH]+[OAc]- (DBU = 1,8-diazabicyclo-[5.4.0] undec-7-ene) has been developed. The reactions are very efficient, affording the corresponding diaryl thioethers in moderate to high yields. Aryl chlorides could also be reacted with carbon disulfide using this protocol. Moreover, [DBUH]+[OAc]- could be easily recovered and reused for several runs.

Unprecedented iminobenzosemiquinone and iminobenzoquinone coordinated mononuclear Cu(ii) complex formation under air

Mondal, Manas Kumar,Biswas, Abul Kalam,Ganguly, Bishwajit,Mukherjee, Chandan

, p. 9375 - 9381 (2015/06/16)

Two non-innocent 2-anilino-4,6-di-tert-butylphenol units were connected through an -ortho bridging S atom and provided the ligand H4LS(AP/AP). The ligand reacted with CuCl2·2H2O in the presence of Et3

Highly efficient and magnetically separable nano-CuFe2O4 catalyzed S-arylation of thiourea by aryl/heteroaryl halides

Hajipour, Abdol R.,Karimzadeh, Morteza,Azizi, Ghobad

, p. 1382 - 1386 (2015/02/19)

The non-toxic and magnetically separable nano-CuFe2O4 catalyzed synthesis of symmetrical aryl sulfides by the reaction of thiourea with a wide variety of aryl halides, including aryl chlorides has been reported. Excellent yields of products have been obtained under ligand-free conditions and without the use of any expensive catalyst, such as palladium.

Synthesis of diaryl thioethers from aryl halides and potassium thiocyanate

Hajipour, Abdol R.,Pourkaveh, Raheleh,Karimi, Hirbod

, p. 879 - 883 (2015/02/05)

An efficient palladium catalyst was synthesized using nicotine, benzyl chloride and palladium chloride. The structure of this catalyst was characterized and it was then used for the synthesis of diaryl sufides. A variety of diaryl thioethers were synthesized under relatively mild reaction conditions. This protocol avoids foul-smelling thiols via cross-coupling of aryl halides with potassium thiocyanate and all substrates give the corresponding products in good to excellent yields in the presence of low amounts of the catalyst.

A simple and green synthesis of diaryl sulfides catalyzed by an MCM-41-immobilized copper(I) complex in neat water

Cai, Mingzhong,Xiao, Ruian,Yan, Tao,Zhao, Hong

, p. 55 - 60 (2013/10/22)

The heterogeneous carbon-sulfur bond formation reaction of aryl iodides with potassium thiocyanate was achieved in neat water at 130 C by using 5 mol% MCM-41-immobilized bidentate nitrogen/CuCl complex [MCM-41-2N-CuCl] as catalyst and Cs2CO3 as base, yielding a variety of diaryl sulfides in moderate to high yields. This heterogeneous copper catalyst can be easily prepared by a simple two-step procedure from commercially available and cheap reagents and recovered by a simple filtration and reused for 10 cycles without loss of catalytic activity.

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