10436-57-4

Usage

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 4185, 1988 DOI: 10.1016/S0040-4039(00)80451-7

InChI:InChI=1/C9H10OS/c1-7-5-3-4-6-9(7)11-8(2)10/h3-6H,1-2H3

Upstream product

• 75-36-5 acetyl chloride 
• 137-06-4 2-thiocresol 
• 108-24-7 acetic anhydride 
• 95-53-4 o-toluidine 
• 10387-40-3 potassium thioacetate 
• 108-22-5 Isopropenyl acetate 
• 64-19-7 acetic acid 
• 615-37-2 ortho-methylphenyl iodide 
• 95-46-5 2-methylphenyl bromide 
• 2093-46-1 2-methylphenyl diazonium tetrafluoroborate 

Downstream Products

• 63369-67-5 2-methylbenzenesulfinyl chloride 
• 14664-64-3 2-methylbenzenesulfenyl chloride 
• 75-36-5 acetyl chloride 

Relevant academic research and scientific papers

Fungicidal Activity of S-Esters of Thiocarboxylic Acids as Antimicrobial Additives to Petroleum Products

Abstract: A variety of aliphatic and aromatic S-esters of thiocarboxylic acids have been tested for antimicrobial activity. The relationship between the chemical structure of the compounds R1SC(O)R2 and their toxicity for microorganisms has been revealed, and the effect of various functional groups on the antimicrobial properties has been shown. The cooling lubricant IKhP-45E with S-aryl thioacetate additives has been tested. It has been shown that the additives used (0.25–0.5 wt %) inhibit the growth of all the studied microorganisms; however, their activity with respect to fungi is higher. The introduction of S-aryl thioacetates provides the resistance of these oils to microbiological deterioration to retain the physicochemical properties for a long period of time.

Methanesulfonic anhydride-promoted sustainable synthesis of thioesters from feedstock acids and thiols

Abstract: An unprecedented metal-, halogen- and solvent-free, MSAA-promoted S-carbonylation of thiols with feedstock acids has been developed. This new transformation provides an efficient and atom-economic strategy for the synthesis of thioesters in a single operation from readily available and inexpensive starting materials. The reaction avoids the use of expensive and hazardous coupling reagents, bases and generates water as the only by-product, thus making this chemical synthetic process more viable, environment-friendly and contributing towards sustainable chemistry. Graphic abstract: [Figure not available: see fulltext.].

Thioesters as Bifunctional Reagents for 2-Naphthylamine Sulfuracylation

An efficient and convenient strategy for the preparation of diaryl sulfides via a Fe-promoted direct sulfuracylation of 2-naphthylamine using thioesters as bifunctional reagents is described. This synthetic strategy features high chemoselectivity, good substrate scope and functional group tolerance. (Figure presented.).

S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters

This paper demonstrates an efficient, mild, and chemoselective synthesis of various thioesters via a HOTf-catalyzed S-acetylation of aromatic and aliphatic thiols using isopropenyl acetate as a cheap and convenient acetylating agent. During our tests, we also investigated the differences between the activities of metal triflates and triflic acid as catalysts in the acetylation of thiols. Finally, the potential of our concept has been increased by the implementation of Nafion as a heterogeneous catalyst for S-acetylation of thiols.

Efficient Cu-catalyzed base-free C-S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides

S-aryl thioacetates can be prepared by reaction of inexpensive potassium thioacetate with both electron-rich and electron-poor aryl iodides under a base-free copper/ligand catalytic system. CuI as copper source affords S-aryl thioacetates in good to excellent yields, by using 1,10-phenanthroline as a ligand in toluene at 100°C after 24 h. Under microwave irradiation the time was drastically reduced to 2 h. Both procedures are simple and involve a low-cost catalytic system. This methodology was also applied to the "one-pot" synthesis of target heterocycles, such as 3H-benzo[c][1,2]dithiol-3-one and 2-methylbenzothiazole, alkyl aryl sulfides, diaryl disulfides and asymmetric diaryl sulfides in good yields.

Rapid and convenient synthesis of S-acetylarenethiols by non-aqueous diazotization

A series of S-acetylarenethiols were synthesized from aromatic amines by a rapid, convenient and efficient method. Arenediazonium tetrafluoroborates were afforded from aromatic amines, isoamyl nitrite and boron trifluoride etherate in non-aqueous diazotization system, then reacted with potassium thioacetate in dimethylsulfoxide to obtain desired products in moderate to good yields and short reaction times. The product S-acetyl-4-iodothiophenol was characterized by single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/C with unit cell parameters: a = 0.594 20(12) nm, b = 0.542 00(11) nm, c = 2.9618(6) nm, α = 90.00°, β = 94.23(3)°, γ = 90.00°, Dx = 1.942 g/cm3, Z = 4, F(000) = 528, μ = 3.528 mm-1, R = 0.039 2, wR = 0.099 3, P = (Fo2 + 2Fc2)/3, S = 1.077, (Δρ)max = 0.692 x 1030 e/m3, (Δρ)min = -0.558 x 1030 e/m3. The X-ray crystallographic structure (CCDC-684683) clearly shows that the para atoms I and S lie in the benzene ring plane and no hydrogen bonds were observed.

Efficient preparation of S-aryl thioacetates from aryl halides and potassium thioacetate

A method for the preparation of S-aryl thioacetates using palladium-mediated couplings of aryl bromides and aryl triflates with potassium thioacetate as an inexpensive thiol source was developed. Electron withdrawing groups, electron donating groups and heterocyclic substrates were tolerated in the reaction conditions, affording the corresponding products in good to excellent yields. This method was applied to the preparation of novel sulfone-containing DPP-IV inhibitors.

THE REACTIVITY OF SULFUR NUCLEOPHILES TOWARDS ARENEDIAZONIUM TETRAFLUOROBORATES IN APROTIC SOLVENTS: SYNTHESIS OF S-ARYL THIOACETATES

Various S-aryl thioacetates are prepared in 40-60percent yield by treatment of arenediazonium tetrafluoroborates with commercial potassium thioacetate in DMSO at room temperature.