2943-42-2

Basic information

• Product Name: p-Toluenethiosulfonic acid S-p-tolyl ester
• Synonyms: 4-Methylbenzenesulfonothioic acid S-(4-methylphenyl) ester;p-Toluenesulfonothioic acid S-p-tolyl ester;p-Toluenethiosulfonic acid S-p-tolyl ester;p-Tolyl(p-tolylsulfonyl) sulfide;NSC 86030;p-Tolyl p-toluenethiolsulfonate;p-Tolyl p-toluenethiosulfonate;S-p-Tolyl p-toluenethiolsulfonate
• CAS NO: 2943-42-2
• Molecular Formula: C₁₄H₁₄O₂S₂
• Molecular Weight: 278.3898
• Mol File: 2943-42-2.mol

Chemical Properties

• Melting Point: 75-77℃
• Boiling Point: 432.5°Cat760mmHg
• Flash Point: 215.4°C
• Appearance: /
• Density: 1.28
• Vapor Pressure: 2.78E-07mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: p-Toluenethiosulfonic acid S-p-tolyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: p-Toluenethiosulfonic acid S-p-tolyl ester(2943-42-2)
• EPA Substance Registry System: p-Toluenethiosulfonic acid S-p-tolyl ester(2943-42-2)

Safety Data

• Hazardous Substances Data: 2943-42-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
p-Toluenethiosulfonic acid S-p-tolyl ester is used as a reagent in organic synthesis for the formation of carbon-sulfur bonds. Its ability to create these bonds makes it a crucial component in the synthesis of various sulfur-containing compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, p-Toluenethiosulfonic acid S-p-tolyl ester is utilized in the production of various drugs. Its unique chemical properties contribute to the development of new and innovative pharmaceutical compounds.
Used in Agrochemical Production:
p-Toluenethiosulfonic acid S-p-tolyl ester also finds applications in the agrochemical industry. It is used in the synthesis of various agrochemicals, such as pesticides and herbicides, due to its ability to form carbon-sulfur bonds and create diverse sulfur-containing compounds.

InChI:InChI=1/C14H14O2S2/c1-11-3-7-13(8-4-11)17-18(15,16)14-9-5-12(2)6-10-14/h3-10H,1-2H3

Upstream product

• 110-86-1 pyridine 
• 106-45-6 para-thiocresol 
• 98-59-9 p-toluenesulfonyl chloride 
• 71-43-2 benzene 
• 933-00-6 p-methylbenzenesulfenyl chloride 
• 536-57-2 p-toluene sulfinic acid 
• 59-88-1 phenylhydrazine hydrochloride 
• 103-19-5 di(p-tolyl) disulfide 
• 14933-92-7 p-toluenesulfenanilide 
• 3541-14-8 phenyl toluene-4-thiosulfonate 
• 109042-83-3 toluene-4-sulfinic acid-anhydride 
• 100-65-2 N-Phenylhydroxylamine 
• 64-17-5 ethanol 
• 17356-08-0 thiourea 

Downstream Products

• 623-13-2 4-methylphenyl methylsulfide 
• 103-19-5 di(p-tolyl) disulfide 
• 620-94-0 di-(p-tolyl)sulfane 
• 104-15-4 toluene-4-sulfonic acid 
• 536-57-2 p-toluene sulfinic acid 
• 10381-70-1 benzyl 4-methylphenyl sulfoxide 
• 111296-37-8 N-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-N-(4-hydroxy-1-methyl-2-p-tolyldisulfanyl-but-1-en-t-yl)-formamide 
• 3699-01-2 4-tolyl phenyl sulfide 
• 135-58-0 Mesulfen 
• 10409-07-1 bis(4-methylphenyl)disulfone 
• 3996-29-0 2-[(4-methylphenyl)thio]acetic acid 
• 5395-20-0 1-methyl-4-(benzylsulfonyl)benzene 
• 736977-06-3 4-chloro-1-nitro-2-tosylbenzene 
• 899-02-5 (2,4-dinitro-phenyl)-p-tolyl sulfone 

Relevant articles and documents

(Thio)etherification of Quinoxalinones under Visible-Light Photoredox Catalysis

An efficient visible-light-induced (thio)etherification of quinoxalin-2(1H)-ones with divergent aliphatic alcohols and thiols (primary, secondary, and tertiary) at room temperature in air has been developed. This protocol was highlighted by its mild conditions, readily available starting materials, operational simplicity, and wide functional group tolerance. (Figure presented.).

Oxidation of bis-sulfinyl carbanions as the pivot of ionic/radical tandem reactions

[1,4]-additions of various nucleophiles such as lithiated carbamates, alkoxides or ester enolates onto enantiopure alkylidene bis-sulfoxides proceed with high diastereoselectivity. The oxidation of the resulting carbanions with iron(III) salts induces the

Facile Conversion of Thiosulfinic S-Ester to Sulfinic Ester

Thiosulfinic S-esters are readily converted to the corresponding sulfinic esters in good yields by treating in alcohols with a catalytic amount of I2, Br2, or HCl in the presence of H2O2, replacing sulfenyl groups by alcohols.The mechanism of this reaction is also discussed.

Second monoclinic polymorph of S-(4-tolyl) 4-toluenethiosulfonate at 150 and 293 K

The structure of S-(4-tolyl) 4-toluenethiosulfonate is described at 150 and 293 K. The compound does not contain intermolecular C-H···O hydrogen bonds. Compared to another polymorph, the compound's crystal structure have effective acceptors in the form of

Vibrational and NMR spectroscopic studies of a thiolsulphonate produced from the non-catalytic hydrogenation of polybutadiene

Mass spectrometry, 1H NMR, 13C NMR, 2D NMR, FT-IR and Raman spectroscopy have been used to established the structure of a thiosulphonate by-product in the non-catalytic hydrogenation process for polybutadiene, which makes use of p-toluene sulphonylhydrazi

Reaction of primary thioamides with p-toluenesulfinic acid

The conversion of thioamides to the corresponding 1,2,4-thiadiazoles occurs upon heating primary thioamides with formaldehyde and p-toluenesulfinic acid in water instead of the formation of N-(tosylmethyl)thioamides. 1997 Plenum Publishing Corporation.

Oxidation of Symmetric Disulfides with Hydrogen Peroxide Catalyzed by Methyltrioxorhenium(VII)

Organic disulfides with both alkyl and aryl substituents are oxidized by hydrogen peroxide when CH3ReO3 (MTO) is used as a catalyst. The first step of the reaction is complete usually in about an hour, at which point the thiosulfinate, RS(O)SR, can be detected in nearly quantitative yield. The thiosulfinate is then converted, also by MTO-catalyzed oxidation under these conditions, to the thiosulfonate and, over long periods, to sulfonic acids, RSO3H. In the absence of excess peroxide, RS(O)SR (R = p-tolyl), underwent disproportionation to RS(O)2SR and RSSR. Kinetics studies of the first oxidation reaction established that two peroxorhenium compounds are the active forms of the catalyst, CH3ReO2(η2-O2) (A) and CH3ReO(η2-O2)2·(OH 2) (B). Their reactivities are similar; typical rate constants (L mol-1 s-1, 25°C, aqueous acetonitrile) are kA = 22, kB = 150 (Bu2S2) and kA = 1.4, kB = 11 (Tol2S2). An analysis of the data for (P-XC6H4)2S2 by a plot of log kB against the Hammett σ constant gave ρ = -1.89, supporting a mechanism in which the electron-rich sulfur attacks a peroxo oxygen of intermediates A and B.

Synthesis of Symmetrical and Unsymmetrical Thiosulfonates from Disulfides through Electrochemically Induced Disulfide Bond Metathesis and Site-Selective Oxidation

The anodic generation of symmetrical and unsymmetrical thiosulfonates is presented. First, the oxidation of disulfides yielding symmetrical thiosulfonates was realized. The direct synthesis is performed using a simple quasi-divided cell design, whereby using a supporting electrolyte is unnecessary. Its principle was then expanded to the conversion of unsymmetrical disulfides that were generated in situ through metathesis of two symmetrical disulfides. This enables a direct access to unsymmetrical thiosulfonates without any pre-functionalization or elaborate synthesis of the starting materials for the first time. The reaction scope was investigated by converting differently functionalized aliphatic and aromatic disulfides in moderate to very good yields. Furthermore, a sensitivity assessment for an improved reproducibility and a robustness screen to determine the compatibility of the reaction against functional groups were performed.

Tetrabutylammonium Iodide Mediated Sulfenylation of Poly-substituted 1 H -Pyrazol-5-amines with Arylsulfonyl Hydrazides

A TBAI-mediated sulfenylation of N,3-diaryl-1-arylsulfonyl-1H-pyrazol-5-amines with arylsulfonyl hydrazides has been established, and an expanded inventory of N,5-diaryl-4-(arylthio)-1H-pyrazol-3-amines was constructed through C-S bond formation and N-S bond breaking. Mechanistic investigations suggest thiosulfonate as a key intermediate in the sulfenylation, and the detosylation is promoted by the generated arylsulfinic acid. The method is characterized by simple operating conditions, broad substrate range as well as gramscale reaction.

Deoxygenative C-S Bond Coupling with Sulfinates via Nickel/Photoredox Dual Catalysis

The C-S bond formation from aryl halides and thiols has been well established under various catalytic systems. In this work, user-friendly sulfinates have been exploited as an efficient sulfenylating reagent in the C-S couplings through visible-light-induced photo/nickel dual catalysis under base- and external reductant-free conditions. A large number of aryl sulfide products were accessed with high selectivity and high tolerance of various functionalities.