3996-30-3

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(m-Methylphenylthio)acetic acid is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Organic Chemistry:
In the field of organic chemistry, 2-(m-Methylphenylthio)acetic acid serves as a building block, facilitating the creation of complex organic molecules and contributing to advancements in chemical research and innovation.
Used in Drug Development and Discovery:
Due to its various biological and pharmacological activities, 2-(m-Methylphenylthio)acetic acid is used as a potential candidate in drug development and discovery, aiding in the creation of novel therapeutic agents.
It is important to handle and store 2-(m-Methylphenylthio)acetic acid with care, as it is a hazardous chemical that may cause skin and eye irritation, as well as respiratory and digestive tract problems if not handled properly.

InChI:InChI=1/C9H10O2S/c1-7-3-2-4-8(5-7)12-6-9(10)11/h2-5H,6H2,1H3,(H,10,11)

Upstream product

• 108-40-7 toluene-3-thiol 
• 79-11-8 chloroacetic acid 
• 124-38-9 carbon dioxide 
• 4886-77-5 3-methylthioanisole 
• 33733-73-2 3-bromo-1-(methylthio)benzene 

Downstream Products

• 16587-47-6 6-methylbenzo[b]thiophene 
• 91367-06-5 (4-chloro-3-methyl-phenylsulfanyl)-acetic acid 
• 90483-65-1 (4-bromo-3-methyl-phenylsulfanyl)-acetic acid 
• 3996-43-8 meta-methylphenylsulfinylacetic acid 
• 14738-26-2 ethyl 2-(m-tolylthio)acetate 
• 20333-41-9 bis(3-methylphenyl)disulfide 
• 17067-19-5 <4-Benzoyl-3-methyl-phenylmercapto>-essigsaeure 
• 92017-05-5 (4-Acetyl-3-methyl-phenylmercapto)-essigsaeure 
• 108-40-7 toluene-3-thiol 
• 2394-00-5 Bis-(m-tolylsulfonyl)-methan 
• 1388725-89-0 8-{[(3-methylphenyl)sulfanyl]methyl}caffeine 
• 18757-53-4 {AgC₉H₁₀O₂S}⁽¹⁺⁾ 
• 83445-73-2 [Cu₂(PAP)(m-tolylSCH₂COO)4] 
• 95125-16-9 Bis-(4-acetyl-3-methyl-phenyl)-disulfid 

Relevant academic research and scientific papers

Electrophilic and nucleophilic pathways in ligand oxide mediated reactions of phenylsulfinylacetic acids with oxo(salen)chromium(V) complexes

The mechanism of oxidative decarboxylation of phenylsulfinylacetic acids (PSAA) by oxo(salen)Cr(V)+ ion in the presence of ligand oxides has been studied spectrophotometrically in acetonitrile medium. Addition of ligand oxides (LO) causes a red shift in the λmax values of oxo(salen) complexes and an increase in absorbance with the concentration of LO along with a clear isobestic point. The reaction shows first-order dependence on oxo(salen)-chromium(V)+ ion and fractional-order dependence on PSAA and ligand oxide. Michaelis-Menten kinetics without kinetic saturation was observed for the reaction. The order of reactivity among the ligand oxides is picoline N-oxide > pyridine N-oxide > triphenylphosphine oxide. The low catalytic activity of TPPO was rationalized. Both electron-withdrawing and electron-donating substituents in the phenyl ring of PSAA facilitate the reaction rate. The Hammett plots are non-linear upward type with negative ρ value for electron-donating substituents, (ρ- = -0.740 to -4.10) and positive ρ value for electron-withdrawing substituents (ρ+ = +0.057 to +0.886). Non-linear Hammett plot is explained by two possible mechanistic scenarios, electrophilic and nucleophilic attack of oxo(salen)chromium(V)+-LO adduct on PSAA as the substituent in PSAA is changed from electron-donating to electron-withdrawing. The linearity in the log k vs. Eox plot confirms single-electron transfer (SET) mechanism for PSAAs with electron-donating substituents.

A paradigm shift in rate determining step from single electron transfer between phenylsulfinylacetic acids and iron(III) polypyridyl complexes to nucleophilic attack of water to the produced sulfoxide radical cation: a non-linear Hammett

Mechanism of oxidative decarboxylation of phenylsulfinylacetic acids (PSAAs) by iron(III) polypyridyl complexes in aqueous acetonitrile medium has been investigated spectrophotometrically. An initial intermediate formation between PSAA and [Fe(NN)3]3+ is confirmed from the observed Michaelis–Menten kinetics and fractional order dependence on PSAA. Significant rate retardation with concentration of [Fe(NN)3]3+ is rationalized on the basis of coordination of a water molecule at the carbon atom adjacent to the ring nitrogen of the metal polypyridyl complexes by nucleophilic attack at higher concentrations. Electron-withdrawing and electron-releasing substituents in PSAA facilitate the reaction and Hammett correlation gives an upward ‘V’ shaped curve. The apparent upward curvature is rationalized based on the change in the rate determining step from electron transfer to nucleophilic attack, by changing the substituents from electron-releasing to electron-withdrawing groups. Electron-releasing substituents in PSAA accelerate the electron transfer from PSAA to the complex and also stabilize the intermediate through resonance interaction leading to negative reaction constants (ρ). Conversely, electron-withdrawing groups, while retarding the electron transfer exert an accelerating effect on the nucleophilic attack of H2O which leading to low magnitude of ρ+ compared to high ρ? values of electron-releasing groups. Marcus theory is applied, and a fair agreement is seen with the experimental values. Copyright

Dynamics of cetyltrimethylammonium bromide-mediated reaction of phenylsulfinylacetic acid with Cr(VI): Treatment of pseudo-phase models

The influence of cetyltrimethylammonium bromide, CTAB, on the oxidative decarboxylation of phenylsulfinylacetic acid, PSAA, and several meta- and para-substituted PSAAs by Cr(VI) was investigated in 95 % H2O-5 % CH3CN medium. The rate profile displayed a peculiar trend with an initial rate increase at low CTAB followed by sharp rate inhibition at higher CTAB concentrations. The initial rate acceleration could be explained by strong binding of SO42- on the positively charged micellar surface. The specific partitioning of PSAA in the micellar phase by hydrophobic interaction and the oxidizing species HCrO3+ in aqueous phase by electrostatic repulsion accounted for the rate retardation at higher CTAB concentrations. The Hammett plot with different substituted PSAAs showed excellent correlation affording negative ? value, which supports the proposed mechanism involving the intermediate formation of sulfonium cation. The obtained ? value in CTAB medium was found to be slightly lower than that in aqueous medium. Quantitative analysis of the rate data for the inhibition shown by CTAB was performed using the Menger-Portnoy and the Piszkiewicz pseudo-phase models. The binding constant for PSAA with micelles was evaluated from the Piszkiewicz cooperative model.

Spectral and mechanistic investigation of Oxidative Decarboxylation of Phenylsulfinylacetic Acid by Cr(VI)

The oxidative decarboxylation of phenylsulfinylacetic acid (PSAA) by Cr(VI) in 20% acetonitrile - 80% water (v/v) medium follows overall second order kinetics, first order each with respect to [PSAA] and [Cr(VI)] at constant [H+] and ionic strength. The reaction is acid catalysed, the order with respect to [H+] is unity and the active oxidizing species is found to be HCrO3+. The reaction mechanism involves the rate determining nucleophilic attack of sulfur atom of PSAA on chromium of HCrO3+ forming a sulfonium ion intermediate. The intermediate then undergoes a,β-cleavage leading to the liberation of CO2. The product of the reaction is found to be methyl phenyl sulfone. The operation of substituent effect shows that PSAA containing electron-releasing groups in the meta- and para-positions accelerate the reaction rate while electron withdrawing groups retard the rate. An excellent correlation is found to exist between log k2 and Hammett s constants with a negative value of reaction constant. The p value decreases with increase in temperature evidencing the high reactivity and low selectivity in the case of substituted PSAAs.

Metallation reactions. Part 35: A change of the regiochemistry in the metallation of (alkylthio)arenes

The metallation reaction of bromo(alkylthio)benzenes is described. The results show the complementarity of these reactions with the metal-hydrogen exchange reaction. In fact, monometallation of bromo(methylthio)benzenes afforded products substituted in para or meta or ortho to the thioethereal function while bimetallation led to αS,para, αS,meta and αS,ortho disubstituted products. Analogously, the monometallation of 4-bromo-(isopropylthio)benzene afforded para-monosubstituted and ortho,para-disubstituted products.

KINETICS AND MECHANISM OF OXIDATION OF (ARYLTHIO)ACETIC ACIDS BY PYRIDINIUM HYDROBROMIDE PERBROMIDE

Oxidation of several monosubstituted (phenylthio)acetic acids (PTAA) by pyridinium hydrobromide perbromide (PHPB) was studied in aqueous acetic acid.The reaction is first order with respect to PHPB.Michaelis-Menten type kinetics are observed with respect to (arylthio)acetic acid.The effect of solvent composition indicates that the transition state is more polar than the reactants.The formation constants of the intermediate substrate-PHPB complexes and the rates of their decomposition were determined at different temperatures.The rates of oxidation of para and meta-substituted (phenylthio)acetic acids were correlated with Hammett's substituent constants.The ρ value is -1.60 at 35 deg c.The rates of oxidation of ortho substituted compounds are correlated with Charton's triparametric equation.A mechanism involving the decomposition of the intermediate complex in the slow rate-determining step affording a sulphonium ion which hydrolyses in a subsequent fast step to the sulphoxide is proposed.

Photoredox reactions of polypyridyl chromium (III) complexes with arylthioacetic acids in acetonitrile and aqueous media

The reductive quenching reactions of ,Cr(NN)33+ (NN = 2,2'-bipyridyl, 4,4'-dimethyl-2,2'-bipyridyl and 1,10-phenanthroline) with arylthioacetic acids in acetonitrile and arylthioacetate ions in aqueous media have been studied. The substantial difference in k(q) values between the acetonitrile and aqueous media is traced to the difference in the origin of electron for the reduction of Cr(III) complexes i.e., sulphur in acetonitrile and carboxylate ion in aqueous medium.

METALATION REACTIONS. XIV. REGIOSPECIFIC PREPARATION OF POLYSUBSTITUTED BENZENES VIA MONO- OR DI-LITHIATION REACTIONS OF AROMATIC THIOETHERS

The preparation of polyfunctionalized aromatic thioethers either by one-step dilithiation or by two successive one-flask monometalation reactions is described.By acting on 1 two equal or different electrophiles one on the thiomethyl group and one in the ortho-position with respect to it are introduced; by acting on 11 and on 35 the substitution involves the thiomethyl carbon atom and that in the ortho-position with respect to the alkoxy group.In the case of the homologeous isopropylthio (23) the substitution involves the two aryl carbon atoms in the ortho-position to both functions.In the case of the p-disubstituted isomers (49, 59) analogous behaviour to ortho isomers in one-step metalation reaction is observed, while the two hydrogen atoms in the ortho-positions to the methoxy group are substituted when two successive monometalations are employed.The metalation of 40 results low selective.The behaviour of 79 and 93 is analogous to 1, while 72, 88 and 96 undergo only one-step monometalation reactions.