3058-47-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Nitrothioanisole is used as a synthetic intermediate for the production of various pharmaceuticals. Its unique chemical structure allows it to be a key component in the synthesis of drug molecules, contributing to the development of new medications and therapies.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Nitrothioanisole serves as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity and functional groups enable the creation of effective compounds that protect crops and enhance agricultural productivity.
Used in Organic Synthesis:
2-Nitrothioanisole is utilized as a reagent in organic synthesis, facilitating various chemical reactions and the formation of new compounds. Its presence can enhance the efficiency and selectivity of these reactions, leading to the production of desired products with improved yields.
Used in Dye Preparation:
As a precursor for the preparation of dyes, 2-Nitrothioanisole contributes to the coloration and staining processes in various industries, such as textiles, plastics, and printing inks. Its chemical properties allow for the development of dyes with specific characteristics, including color intensity and stability.
Used in Manufacturing Industry:
The versatile nature of 2-Nitrothioanisole makes it a valuable building block in the manufacturing industry. Its ability to participate in numerous chemical reactions and form a wide array of compounds positions it as a crucial component in the production of various industrial products.

InChI:InChI=1/C7H7NO2S/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5H,1H3

Upstream product

• 1155-00-6 bis(2-nitrophenyl)disulfide 
• 74-93-1 methylthiol 
• 88-73-3 2-Chloronitrobenzene 
• 67-68-5 dimethyl sulfoxide 
• 13118-30-4 dimethyl-(2-nitro-phenyl)-sulfonium ; methyl sulfate 
• 1493-27-2 ortho-nitrofluorobenzene 
• 5188-07-8 sodium thiomethoxide 
• 4875-10-9 o-nitrothiophenol 
• 74-88-4 methyl iodide 
• 75355-13-4 2-nitrophenyl sulphide anion 
• 67-56-1 methanol 
• 22024-99-3 2-nitrobenzenesulfenyl bromide 
• 594-27-4 tetramethylstannane 
• 7669-54-7 2-nitrobenzenesulfenyl chloride 

Downstream Products

• 856356-44-0 bis-(2-methylsulfanyl-phenyl)-diazene-N-oxide 
• 2987-53-3 2-(Methylthio)aniline 
• 15436-25-6 S-Methyl-S-<2-nitro-phenyl>-N-p-toluolsulfonyl-sulfilimin 
• 2976-34-3 1-(methylsulfonyl)-2-nitrobenzene 
• 224635-35-2 3-methylthio-4-[3-(2-methylphenyl)ureido]phenylacetic acid 
• 857770-01-5 N,N'-bis-(2-methylsulfanyl-phenyl)-hydrazine 
• 345635-46-3 4-bromo-1-methylsulfanyl-2-nitro-benzene 
• 132016-28-5 methyl-(2-nitro-phenyl)-sulfoxide 
• 107682-72-4 bis-(2-methylsulfanyl-phenyl)-diazene 
• 6278-86-0 N₂-(4-bromophenyl)-1,3-benzothiazol-2-amine 
• 1843-21-6 N-phenyl-2-benzothiazolamine 
• 24622-31-9 N-butylbenzo[d]thiazol-2-amine 
• 24255-48-9 N,N-diethylbenzo[d]thiazol-2-amine 
• 19983-29-0 2-(pyrrolidin-1-yl)benzo[d]thiazole 

Relevant academic research and scientific papers

Stabilisation of Nitrophenyl Disulphide Ions in Dimethylacetamide

2-Nitrophenyl and 4-nitrophenyl disulphide ions are stabilised in aprotic dipolar solvents and solutions of these ions are obtained in dimethylacetamide by nucleophilic attack of sulphur by the corresponding thiolates.

Copper-Catalyzed Methylthiolation of Aryl Iodides and Bromides with Dimethyl Disulfide in Water

An efficient route to aryl methyl sulfides through the copper-catalyzed coupling reaction of aryl iodides or bromides with dimethyl disulfide in water is described. Electron-donating and electron-withdrawing functional groups in the substrates were tolerated, and the corresponding products were obtained in moderate to good yields.

Preparation method of o-aminothiophenol

The invention provides a preparation method of o-aminothiophenol. The preparation method comprises the following steps: putting o-chloronitrobenzene into sodium methyl mercaptide, and performing heating under the action of a catalyst to carry out a methyl vulcanization reaction so as to prepare o-nitrophenyl dimethyl sulfide; putting o-nitrophenyl thioether into a solvent, and carrying out hydrogenation reduction to prepare o-aminobenzene thioether; and demethylating the o-aminothiophenol under the action of hydrobromic acid to obtain the o-aminothiophenol. The preparation method of o-aminothiophenol has the advantages of high yield and high product purity.

N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids

Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.

Industrial production method of o-nitrobenzenesulfonyl chloride

The invention discloses an industrial production method of o-nitrobenzenesulfonyl chloride. The method comprises the following steps that o-nitrochlorobenzene and sodium methyl mercaptide are subjected to an etherification reaction, filtering is conducted, an obtained filter cake is subjected to recrystallization, and through centrifugation separation and drying, a dry product of o-nitrobenzene dimethyl sulfide is obtained; the dry product of o-nitrobenzene dimethyl sulfide is subjected to a chlorination reaction in batches to obtain a wet crude product, an appropriate amount of hydrochloric acid is added in a chlorination reaction system, the chlorination reaction is carried out in a hydrophilic organic acid solvent, and the mole ratio of the o-nitrobenzene dimethyl sulfide to water during the chlorination reaction is 1:(5-15); a finished product of o-nitrobenzenesulfonyl chloride is obtained through refining and drying. Through HPLC detection, the content of the o-nitrobenzenesulfonyl chloride synthesized by means of the method is 98-98.5%; the yield is 0.72-0.75, the acquisition rate is 0.97 or above, the turbidity (ppm) is 1.5-2, and the melting point is 66-67 DEG C. By adopting the hydrophilic organic acid solvent, the problems about large-scale production discharging, yield and quality are solved, and meanwhile the purposes of mixed application and post-treatment separation of large-scale production water-soluble solvents are achieved.

Metal-free S-methylation of diaryl disulfides with di-tert-butyl peroxide

An efficient approach for S-methylation of diaryl disulfides with di-tert-butyl peroxide under metal-free and neutral conditions was established. The present protocol shows good functional group tolerance to afford aryl methyl sulfides in moderate to good

2-Nitrobenzenesulfonyl chloride and synthetic method and application thereof

The invention discloses 2-nitrobenzenesulfonyl chloride and a synthetic method and application thereof; the synthetic method comprises the steps of (a) subjecting 2-nitrochlorobenzene and sodium thiomethoxide to etherification, filtering, recrystallizing the obtained filter cake, centrifugally separating, and drying to obtain dried 2-nitrophenyl sulfur ether; (b) chlorinating the dried 2-nitrophenyl sulfur ether to obtain a wet crude product; refining, and drying to obtain the finished 2-nitrobenzenesulfonyl chloride. By modifying the prior art, it is possible to eliminate the intermediate product, disulfides, with the turbidity of the product fully controlled to 2 and below, and the requirement of liquid crystal materials for the turbidity is met; compared with the prior art, the 2-nitrobenzenesulfonyl chloride and the synthetic method and application thereof have the advantages that the process cost is low and the more applications of 2-nitrobenzenesulfonyl chloride are available in the field of liquid crystal materials and other fields.

Copper-catalyzed decarboxylative methylthiolation of aromatic carboxylate salts with DMSO

A novel copper-catalyzed decarboxylative methylthiolation of arenecarboxylate salts has been realized using DMSO as the methylthiolation source. Various potassium aryl carboxylates underwent decarboxylative methylthiolation under air to furnish the corresponding aryl methyl thioethers in moderate to excellent yields. The reaction tolerated a wide variety of functional groups. Notably, the synthesis of ethylthioethers was also successfully achieved directly from diethyl sulfoxide under similar reaction conditions.

Metal-free radical thiolations mediated by very weak bases

Aromatic thioethers and analogous heavier chalcogenides were prepared by reaction of arene-diazonium salts with disulfides in the presence of the cheap and weak base NaOAc. The mild and practical reaction conditions (equimolar reagents, DMSO, r.t., 8 h) tolerate various functional groups (e.g. Br, Cl, NO2, CO2R, OH, SCF3, furans). Mechanistic studies indicate the operation of a radical aromatic substitution mechanism via aryl, acetyloxyl, thiyl, and dimsyl radicals.

Rh-POP pincer Xantphos complexes for C-S and C-H activation. Implications for carbothiolation catalysis

The neutral Rh(I)-Xantphos complex [Rh(κ3-P,O,P-Xantphos)Cl]n, 4, and cationic Rh(III) [Rh(κ3-P,O,P-Xantphos)(H)2][BArF4], 2a, and [Rh(κ3-P,O,P-Xantphos-3,5-C6H3(CF3)2)(H)2][BArF4], 2b, are described [ArF = 3,5-(CF3)2C6H3; Xantphos = 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Xantphos-3,5-C6H3(CF3)2 = 9,9-dimethylxanthene-4,5-bis(bis(3,5-bis(trifluoromethyl)phenyl)phosphine]. A solid-state structure of 2b isolated from C6H5Cl solution shows a κ1-chlorobenzene adduct, [Rh(κ3-P,O,P-Xantphos-3,5-C6H3(CF3)2)(H)2(κ1-ClC6H5)][BArF4], 3. Addition of H2 to 4 affords, crystallographically characterized, [Rh(κ3-P,O,P-Xantphos)(H)2Cl], 5. Addition of diphenyl acetylene to 2a results in the formation of the C-H activated metallacyclopentadiene [Rh(κ3-P,O,P-Xantphos)(ClCH2Cl)(σ,σ-(C6H4)C(H)=CPh)][BArF4], 7, a rare example of a crystallographically characterized Rh-dichloromethane complex, alongside the Rh(I) complex mer-[Rh(κ3-P,O,P-Xantphos)(η2-PhCCPh)][BArF4], 6. Halide abstraction from [Rh(κ3-P,O,P-Xantphos)Cl]n in the presence of diphenylacetylene affords 6 as the only product, which in the solid state shows that the alkyne binds perpendicular to the κ3-POP Xantphos ligand plane. This complex acts as a latent source of the [Rh(κ3-P,O,P-Xantphos)]+ fragment and facilitates ortho-directed C-S activation in a number of 2-arylsulfides to give mer-[Rh(κ3-P,O,P-Xantphos)(σ,κ1-Ar)(SMe)][BArF4] (Ar = C6H4COMe, 8; C6H4(CO)OMe, 9; C6H4NO2, 10; C6H4CNCH2CH2O, 11; C6H4C5H4N, 12). Similar C-S bond cleavage is observed with allyl sulfide, to give fac-[Rh(κ3-P,O,P-Xantphos)( η3-C3H5)(SPh)][BArF4], 13. These products of C-S activation have been crystallographically characterized. For 8 in situ monitoring of the reaction by NMR spectroscopy reveals the initial formation of fac-κ3-8, which then proceeds to isomerize to the mer-isomer. With the para-ketone aryl sulfide, 4-SMeC 6H4COMe, C-H activation ortho to the ketone occurs to give mer-[Rh(κ3-P,O,P-Xantphos)(σ,κ1-4-(COMe)C6H3SMe)(H)][BArF4], 14. The temporal evolution of carbothiolation catalysis using mer-κ3-8, and phenyl acetylene and 2-(methylthio)acetophenone substrates shows initial fast catalysis and then a considerably slower evolution of the product. We suggest that the initially formed fac-isomer of the C-S activation product is considerably more active than the mer-isomer (i.e., mer-8), the latter of which is formed rapidly by isomerization, and this accounts for the observed difference in rates. A likely mechanism is proposed based upon these data.