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Benzene, 1-methyl-4-[(4-nitrophenyl)sulfonyl]-, also known as 4-Methylbenzenesulfonyl chloride or 4-Toluenesulfonyl chloride, is an organic compound with the chemical formula C8H9ClNO3S. It is a colorless to pale yellow crystalline solid that is soluble in organic solvents. Benzene, 1-methyl-4-[(4-nitrophenyl)sulfonyl]- is primarily used as a reagent in organic synthesis, particularly in the preparation of various sulfonamide derivatives and as a protecting group in peptide synthesis. It is also employed in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. Due to its reactivity and potential health hazards, it is important to handle this chemical with care, following proper safety protocols.

4094-37-5

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4094-37-5 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 4094-37-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,0,9 and 4 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 4094-37:
(6*4)+(5*0)+(4*9)+(3*4)+(2*3)+(1*7)=85
85 % 10 = 5
So 4094-37-5 is a valid CAS Registry Number.

4094-37-5Relevant academic research and scientific papers

Visible-light-driven electron donor-acceptor complex induced sulfonylation of diazonium salts with sulfinates

Cheng, Lan,Guo, Jianbo,Li, Yufei,Liang, Xin,Wang, Qingmin,Xia, Qing,Zhang, Pei,Zhang, Weihua

supporting information, p. 8865 - 8870 (2021/11/30)

This work reports an efficient sulfonylation reaction enabled by a visible-light-induced radical coupling reaction between phenyl/heterocyclic diazonium salts and sulfinates. Mechanistic experiments disclosed the formation of a versatile electron donor-acceptor (EDA) complex. This transformation is characterized by an easy operational procedure under mild conditions which avoids transition metals, ligands, catalysts, and oxidants.

Method for synthesizing sulfone compounds under photocatalysis condition

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Paragraph 0159-0163, (2021/03/31)

The invention belongs to the technical field of compound preparation, and particularly relates to a method for synthesizing sulfone compounds under a photocatalysis condition. Aromatic hydrazine and sulfinate are used as raw materials, and under the action of alkali and a solvent, a sulfone compound is generated through reaction under the condition of air or oxygen under the illumination of visible light. According to the method disclosed by the invention, aryl hydrazine is used as an arylation reagent, polyacid salt is used as a catalyst or an organic photosensitizer is used as a catalyst, and the sulfones compound can be efficiently synthesized by coupling with sulfinate under the condition of room temperature through visible light irradiation. The method has good substrate universalityand relatively mild reaction conditions, is not only a substitute for synthesizing sulfone compounds by coupling from simple substrates reported at present, but also broadens the new application of the polyacid salt in the field of photocatalysis.

Mo(VI) complex catalysed synthesis of sulfonees and their modification for anti-HIV activities

Madduluri, Vimal Kumar,Baig, Noorullah,Chander, Subhash,Murugesan, Sankaranarayanan,Sah, Ajay K.

, (2020/01/23)

An efficient method for the synthesis of sulfones has been developed using sugar derived cis-dioxo molybdenum(VI) complex as catalyst and urea hydrogen peroxide as oxygen source. Present method is highly specific for sulfide oxidation irrespective of presence of alkene and aldehyde groups in the same molecule. Synthesis of fifteen sulfones have been reported with 82–98% isolated yields and the catalyst has been reused five times without any loss in its activity. 2-(Phenylsulfonyl)aniline has been condensed with eight different aromatic aldehydes and the products are being explored for HIV-1 reverse transcriptase inhibition activities.

TosMIC and its derivatives as versatile sulfonylating agents for the synthesis of p-toluenesulfonylarenes from aryl halides and arylboronic acids

Ravi Kumar,Ramesh,Banik, Swarnayu,Subba Reddy

, (2020/11/02)

An efficient copper(II) catalyzed sulfonyation of aryl halides has been achieved using TosMIC (p-toluenesulfonylmethyl isocyanide) as a sulfonylating agent. This newly developed sulfonylation approach provides an easy access for the synthesis of diaryl sulfones from aryl bromides, iodides and boronic acids with TosMIC under neutral conditions. This method is useful for the sulfonylation of aryl boronic acids under similar conditions. This is the first report on the sulfonylation of aryl bromides, iodides and boronic acids using TosMIC.

Nano copper catalyzed synthesis of symmetrical/unsymmetrical sulfones from aryl/alkyl halides and p-toluenesulfonylmethylisocyanide: TosMIC as a tosyl source

Phanindrudu, Mandalaparthi,Jaya, Pogula,Likhar, Pravin R.,Tiwari, Dharmendra Kumar

, (2020/05/18)

A magnetically induced nano copper-catalyzed efficient and mild route for the synthesis of diaryl and alkyl/aryl sulfones from aryl/alkyl halides and tosylmethyl isocyanide (TosMIC) has been developed. A variety of aryl and alkyl sulfones have been obtained in very good to excellent yields. Sulfones containing molecules have medicinal relevance as they are known to possess various activities such as antifungal, anti-HIV, antitumor, and anticancer. Herein, a magnetically induced nano copper-catalyzed efficient and mild route for the synthesis of biaryl and alkyl/aryl sulfones from aryl/alkyl halides and tosylmethyl isocyanide (TosMIC) has been developed. A variety of aryl and alkyl sulfones have been obtained in very good to excellent yields. In this newly developed protocol TosMIC acts as sulfonyl source. The catalyst can magnetically be recovered and recycled five times without significant loss in activity.

Organic photoredox catalysis enabled cross-coupling of arenediazonium and sulfinate salts: Synthesis of (un)symmetrical diaryl/alkyl aryl sulfones

Chawla, Ruchi,Yadav, Lal Dhar S.

supporting information, p. 4761 - 4766 (2019/05/24)

We disclose herein the first transition-metal-and external oxidant/reductant-free visible-light-mediated synthesis of (un)symmetrical diaryl/alkyl aryl sulfones from arenediazonium tetrafluoroborates and sodium sulfinates using eosin Y as an organic photoredox catalyst. The utilization of visible light as an inexpensive and ecosustainable energy source, operational simplicity, ambient temperature and clean reaction in aqueous acetonitrile are the salient features of the developed protocol. The desired sulfones were also synthesized via a one-pot, two-step process directly from anilines and sulfinate salts in good to excellent yields.

A Convenient Synthesis of Sulfones via Light Promoted Coupling of Sodium Sulfinates and Aryl Halides

Chen, Lei,Liang, Jie,Chen, Zhen-yu,Chen, Jie,Yan, Ming,Zhang, Xue-jing

, p. 956 - 960 (2019/01/25)

A convenient and e?cient synthesis of sulfones from sulfinates and aryl halides was developed. The reaction occurred under UV irradiation without transition metal catalyst or photocatalyst. A radical pathway via single-electron transfer (SET) of electron donor-acceptor (EDA) complex was proposed based on UV-vis spectroscopy, radical inhibiting and trapping experiments. (Figure presented.).

A practical synthesis of aryl sulfones via cross-coupling of sulfonyl hydrazides with aryltriazenes using copper/ionic liquid combination

Pandey, Anand Kumar,Kumar, Saurabh,Singh, Rahul,Singh, Krishna Nand

supporting information, p. 6704 - 6709 (2018/10/15)

A new and efficient approach adopting copper-catalyzed cross-coupling of sulfonyl hydrazides with aryltriazenes has been developed to synthesize aryl sulfones using Br?nsted acidic ionic liquid as promoter under ambient conditions. The process employs stable and easy to handle reacting partners, and is endowed with broad substrate scope.

Copper catalyzed synthesis of unsymmetrical diaryl sulfones from an arenediazonium salt and sodium p-toluenesulfinate

Gund, Sitaram Haribhau,Shelkar, Radheshyam Suresh,Nagarkar, Jayashree Milind

, p. 62926 - 62930 (2015/08/06)

Aryl sulfones have been for the first time synthesized by the reaction of sodium p-toluenesulfinate and arenediazonium salts using a CuI catalyzed homogeneous system. The developed protocol is a simple and efficient new route for the synthesis of diaryl sulfones with excellent product yields. The mild reaction conditions tolerate a range of functional groups. The best results were obtained with CuI, N,N′-dimethylethylenediamine, TBAI and K2CO3 in dimethyl sulfoxide at 100°C under an inert atmosphere.

First palladium-catalyzed denitrated coupling of nitroarenes with sulfinates

Tian, Heng,Cao, Aijuan,Qiao, Lijun,Yu, Ajuan,Chang, Junbiao,Wu, Yangjie

supporting information, p. 9107 - 9112 (2015/03/05)

The first example of palladium-catalyzed protocol for the denitrated coupling of nitroarenes with sulfinates was developed, achieving aryl and heterocyclic sulfones in moderate to excellent yields. The cyclopalladated ferrocenylimine (I) exhibited highly catalytic activity for this transformation with low catalyst loading (0.75 mol %). The efficiency of this reaction was demonstrated by compatibility with a wide range of groups. Thus, the method represents a simple and facile procedure to access aryl and heterocyclic sulfones.

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