7205-63-2

Usage

Functional groups

Nitro group (-NO2), Thioether group (-S)

Structure

Nitrobenzene derivative with a thioether group attached to the benzene ring

Reactivity

Potent electrophile in organic reactions due to the presence of the nitro group

Reagent

Used in organic synthesis and as a reagent in chemical reactions

Applications

Precursor in the production of various chemicals and pharmaceuticals

Importance

Significant chemical in the field of organic chemistry with various applications in industry and research

InChI:InChI=1/C9H11NO2S/c1-7(2)13-9-5-3-8(4-6-9)10(11)12/h3-7H,1-2H3

Upstream product

• 75-30-9 2-iodo-propane 
• 45797-13-5 4-nitrophenylthiolate 
• 20607-43-6 sodium isopropanethiolate 
• 100-00-5 4-chlorobenzonitrile 
• 1849-36-1 para-nitrobenzenethiol 
• 100-25-4 para-dinitrobenzene 
• 2137-92-0 4-nitrophenyl thiocyanate 
• 67-63-0 isopropyl alcohol 
• 13113-79-6 sodium 4-nitrobenzenethiolate 
• 75-33-2 2-propanethiol 
• 350-46-9 4-Fluoronitrobenzene 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 75-26-3 isopropyl bromide 

Downstream Products

• 7205-84-7 2-propyl 4-nitrophenyl sulfone 
• 7205-73-4 isopropyl 4-nitrophenyl sulfoxide 
• 70398-85-5 1,4-Bisbenzene 
• 25355-76-4 (4-Aminophenyl)-isopropyl-sulfon 
• 85002-65-9 1,2,3-Trimethoxy-5-[2-(4-nitro-phenoxy)-ethyl]-benzene 

Relevant academic research and scientific papers

Production of alkyl sulfide nitriphenyl

PROBLEM TO BE SOLVED: To provide a production method of nitrophenyl alkyl sulfide capable of efficiently obtaining the nitrophenyl alkyl sulfide of a high purity in good yield. SOLUTION: The production method of the nitrophenyl alkyl sulfide includes a process for mixing a rough product that contains specific nitrophenyl alkyl sulfide with an aliphatic hydrocarbon to extract the nitrophenyl alkyl sulfide to the aliphatic hydrocarbon. COPYRIGHT: (C)2013,JPO&INPIT

Copper-free sonogashira coupling reaction using a trans-spanning 1,2-Bis(2-thienylethynyl)benzene ligand

Novel copper-free Sonogashira coupling reaction of aryl halides with terminal acetylenes proceeded in the presence of 1,2-bis(2-thienylethynyl) benzene (1) as a trans-bidentatable ligand.

(R)-3-(N,N-DIMETHYLAMINO)PYRROLIDINE DERIVATIVES

(R)-3-(N,N-Dimethyiamino)pyrrolidine derivatives of formula (I), wherein the meaning for Cy1 is as disclosed in the description. These compounds are useful as JAK3 kinase inhibitors

A kinetic investigation, supported by theoretical calculations, of steric and ring strain effects on the oxidation of sulfides and sulfoxides by dimethyldioxirane in acetone

The oxidations of alkyl 4-nitrophenyl, and dialkyl, sulfides and sulfoxides by dimethyldioxirane in acetone occur by concerted mechanisms but the sulfides respond differently from the sulfoxides to variation in the alkyl group. The reactions of the sulfides are inhibited by the steric effects of alkyl groups and these predominate over their inductive effects. By contrast, the reactions of these limited sets of sulfoxides are insensitive to alkyl steric effects but there is an indication of steric acceleration when a broader set of sulfoxides is considered. This behaviour is rationalised in terms of the differences in dipolar charge and its solvation between the ground state and transition state for the two types of substrate. The oxidations of cyclic sulfides and sulfoxides also exhibit contrasting behaviour. The reactivity of the sulfides is insensitive to ring strain but is explicable in frontier orbital terms whereas that of the sulfoxides is partly dependent upon the change in ring strain between reactant and product on oxidation, a difference rationalised in terms of the relative positions of the transition states in the reaction coordinates of the two oxidations. The reactivity of 4-, 5- and 6-membered cyclic sulfoxides is also dependent on a ring-size related property of the transition state. Calculations at the B3-LYP/6-31G* level of density functional theory on both ground states and transition states, including simulation of solvation by acetone, strongly support the mechanistic conclusions reached in this and earlier work.

Thiazolopyrimidine modulators of TRPV1

Certain TRPV1-modulating thiazolopyrimidine compounds are described. The compounds may be used in pharmaceutical compositions and methods for treating disease states, disorders, and conditions mediated by TRPV1 activity, such as pain, arthritis, itch, cough, asthma, or inflammatory bowel disease.

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.

CsF-Celite, an efficient solid state reagent for the syntheses of thioesters and thioethers

Coupling reactions of a number of aliphatic, aromatic, and heterocyclic compounds bearing an acidic hydrogen atom attached to sulfur, with alkyl, acyl, benzyl, or benzoyl halides in acetonitrile with cesium fluoride-Celite are described. This procedure is convenient, efficient, and practical for the preparation of thioethers and thioesters. Springer-Verlag 2005.

An alternative approach towards the syntheses of thioethers and thioesters using CsF-Celite in acetonitrile

It has been found that syntheses of thioethers and thioesters of aliphatic, aromatic and heterocyclic compounds, bearing thiol groups, can be accomplished with alkyl, acyl, benzyl or benzoyl halides in acetonitrile and cesium fluoride-Celite. In this manner, compounds like ethanethiol, 1-pentanethiol, thiophenol, 4-methoxythiophenol, 4-nitrothiophenol, and 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, and 2-mercapto-2-thiazoline can be successfully alkylated, acylated, benzylated or benzoylated. This procedure is convenient, efficient and practical for the preparation of thioethers and thioesters.

Photooxidation of alkyl 4-nitrophenyl sulfides and sulfoxides. Observation of oxidative C-S bond cleavage and rearrangement reactions

Alkyl 4-nitrophenyl sulfides and sulfoxides undergo a self-photoinduced, singlet oxygen oxidation to produce a variety of products, including sulfonates and carbonyl compounds formed by the oxidative cleavage of the C-S bond of the sulfides and sulfoxides. Structural rearrangements are observed in the resulting carbonyl compounds formed in the oxidative cleavage of the C-S bond in the tert-amyl and 2-phenylethyl sulfides. An overall mechanism is proposed which involves the formation of peroxysulfoxides and peroxysulfones which undergo heterolytic C-S bond cleavage to form ion pairs which recombine to form persulfenates or persulfinates which then undergo photo- and/or thermallyinduced homolytic O-O bond cleavage to form alkoxy and sulfinyl or sulfonyl radicals. The alkoxy radicals undergo β-scission, disproportionation, or recombination with the sulfonyl radical to form the observed products. These C-S oxidative cleavage reactions have only been rarely observed in the earlier studies on the singlet oxygen oxidation studies of dialkyl sulfides, and are attributed, in part, to the presence of the 4-nitro group on the aromatic ring which greatly affects the susceptibility of the sulfur atom of the sulfides and sulfoxides toward nucleophilic attack, and on the reactivity of the peroxysulfoxides and peroxysulfones toward heterolytic cleavage of the O-S bond.

Influence of Ion Pairing, Steric Effects, and Other Specific Interactions on the Reactivity of Thioanions with Chloronitrobenzenes. Nucleophilic Aromatic Substitution vs Reduction

The reactions in 2-propanol of the isomeric chloronitrobenzenes with thiolate nucleophiles, RS- (R=Me, i-Pr, t-Bu, Ph), have been studied to test for the ability of these representative thioanions of inducing chloride displacement and/or nitro reduction. m-Chloronitrobenzene gives a complex mixture of products, all still retaining the chlorine substituent, via redox processes involving nitro reduction and ring alkylthiolation.In contrast, the ortho and para isomers undergo substitution of chloride according to the addition/elimination SNAr mechanism also when O2 is removed from the reaction environment.Notably, treatment of o- and p-chloronitrobenzene with the oxanion 2-propoxide in oxygen-free i-PrOH results, instead, in nitro reduction.Kinetic and product studies indicate that i-PrS- is more reactive than i-PrO- in both redox and SNAr reactions, the difference in reactivity being, however, considerably greater in the latter process.The MeS- > i-PrS- > PhS- > t-BuS- reactivity order observed in the SNAr reactions is opposite, as far as the aliphatic thiolates are concerned, to the order of basicity.Notably, reactivity drops with increasing bulkiness of the attacking nucleophile.However, kinetic results obtained under conditions of ion paired and of "free" anions and the effects of ion pairing on the kortho/kpara ratios suggest that steric effects in the transition states are scarcely dependent on the bulkiness of the substituent R in the nucleophile RS- and that nucleophilic reactivity is largely determined by the extent of charge concentration on the attacking atom, which, in turn, affects the strength of ion-pairing interactions.