69746-43-6

Usage

Physical form

Yellow crystalline solid

Uses

Intermediate in the production of pharmaceuticals and agrochemicals, building block in organic synthesis, reagent in the synthesis of complex organic molecules, preparation of thiosemicarbazones and thioureas with antimicrobial and antitumor properties, production of dyes, stabilizer in the manufacture of polymers

Toxicity

Toxic, may cause skin and eye irritation upon contact

Handling precautions

Handle with care

Upstream product

• 52928-01-5 4-iodothiophenol 
• 75-36-5 acetyl chloride 
• 34832-35-4 sodium thioacetate 
• 624-38-4 para-diiodobenzene 
• 10387-40-3 potassium thioacetate 
• 540-37-4 p-aminoiodobenzene 
• 84695-07-8 4-[(N,N'-Dimethylcarbamoyl)thio]iodobenzene 
• 84695-12-5 O-p-Iodophenyl N,N-dimethylthiocarbamate 
• 540-38-5 p-Iodophenol 
• 98-61-3 p-Iodobenzenesulfonyl chloride 
• 1514-50-7 4-iodobenzenediazonium tetrafluoroborate 

Downstream Products

• 171005-37-1 Thioacetic acid S-{4-[4-(4-acetylsulfanyl-phenylethynyl)-2-ethyl-phenylethynyl]-phenyl} ester 
• 171005-35-9 thioacetic acid S-[4-(2-ethyl-4-(phenylethynyl)phenylethynyl)phenyl] ester 
• 171005-39-3 Thioacetic acid S-(4-{4-[4-(4-acetylsulfanyl-phenylethynyl)-3-ethyl-phenylethynyl]-3-ethyl-phenylethynyl}-phenyl) ester 
• 307538-03-0 1-[4-(S-acetylthio)phenyl]-2-(diethoxymethyl)acetylene 
• 23939-49-3 S-(4-vinylphenyl) thioacetate 
• 475666-93-4 thioacetic acid S-{4-[5'-(4-acetylsulfanyl-phenylethynyl)-3,3'-dinitro-[2,2']bipyridinyl-5-ylethynyl]-phenyl} ester 

Relevant academic research and scientific papers

Electrochemically grafted single molecule junctions exploiting a chemical protection strategy

Diazonium grafted oligo(phenylene ethynylene) (OPE) monolayers suitable for single molecule conductance studies have been prepared. The surface-bound OPE is prepared from the amino tolan, 4-(2-(4-(2-(triisopropylsilyl)ethynyl)phenyl)ethynyl)benzamine, which is converted to the diazonium derivative in situ, and subsequently attached to a gold substrate using conventional cathodic electrochemical grafting. Multilayer formation is avoided by the presence of the bulky triisopropylsilyl (TIPS) protected ethynyl group. After removal of the TIPS group by treatment with fluoride, the film, now bearing exposed terminal acetylene moieties, is further functionalised by reaction with 1-iodo-4-acetylthiobenzene using Sonogashira coupling chemistry, to create sites bearing a strongly aurophilic top-contacting group. The success of these surface reactions is confirmed using Raman spectroscopy (gap-mode and SHINERS, employing gold nanoparticles and SiO2 coated gold nanoparticles, respectively). It is shown that such thiolate-modified, diazonium-grafted monolayers are suitable for STM-based molecular junction conductance measurements.

Single-molecule conductance of a chemically modified, π-extended tetrathiafulvalene and its charge-transfer complex with F4TCNQ

We describe the synthesis and single-molecule electrical transport properties of a molecular wire containing a π-extended tetrathiafulvalene (exTTF) group and its charge-transfer complex with F4TCNQ. We form single-molecule junctions using the

Reaction pathway change on plasmonic Au nanoparticles studied by surface-enhanced Raman spectroscopy

Gold nanoparticles (Au NPs) are nanoscale sources of light and electrons, which are highly relevant for their extensive applications in the field of photocatalysis. Although a number of research works have been carried out on chemical reactions accelerated by the energetic hot electrons/holes, the possibility of reaction pathway change on the plasmonic Au surfaces has not been reported so far. In this proof-of-concept study, we find that Au NPs change the reaction pathway in photooxidation of alkyne under visible light irradiation. This reaction produces benzil ([sbnd]CO[sbnd]CO[sbnd]) without the presence of Au NPs. In contrast, as indicated by surface-enhanced Raman spectroscopic (SERS) results, the C[sbnd]C triple bonds ([sbnd]C[tbnd]C[sbnd]) adsorbed on Au NPs are converted into carboxyl ([sbnd]COOH) and acyl chloride ([sbnd]COCl) groups. The plasmonic Au NPs not only provide energetic charge carriers but also activate the reactant molecules as conventional heterogeneous catalysts. This study discloses the second role of plasmonic NPs in photocatalysis and bridges the gap between plasmon-driven and conventional heterogeneous catalysis.

Carbazole-Based Tetrapodal Anchor Groups for Gold Surfaces: Synthesis and Conductance Properties

As the field of molecular-scale electronics matures and the prospect of devices incorporating molecular wires becomes more feasible, it is necessary to progress from the simple anchor groups used in fundamental conductance studies to more elaborate anchor

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.

Synthesis of oligo(phenyleneethynylene)s with vertically disposed tetrathiafulvalene units

Functionalized oligo(phenyleneethynylene)s (OPEs) show potential as molecular wires for molecular electronics. A selection of OPEs with vertically disposed extended tetrathiafulvalene (TTF) units has been synthesized by a combination of metal-catalyzed cr

Chemical functionalization of electrodes for detection of gaseous nerve agents with carbon nanotube field-effect transistors

An innovative sensor for the detection of nerve agents in the gas phase based on a carbon nanotube field-effect transistor was developed. A high sensitivity to organophosphorus gases was obtained by modifying gold electrodes with specific tailor-made self

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.

Tetrathiafulvalene-based molecular nanowires

A new molecular wire suitably functionalized with sulfur atoms at terminal positions and endowed with a central redox active TTF unit has been synthesized and inserted within two atomic-sized Au electrodes; electrical transport measurements have been perf

An improved, general procedure to S-aryl thiol esters: A new synthetic application of dry arenediazonium o-benzenedisulfonimides

The reaction between dry arenediazonium o-benzenedisulfonimides (1) and sodium thioacetate or thiobenzoate in anhydrous acetonitrile at room temperature is an efficient and safe procedure, of general validity, for the preparation of S-aryl thiol esters. The products can be easily purified and the yields are always very high. Of the 28 considered examples, the average yield of the S-aryl thioacetates (7) was 86% and that of the S-aryl thiobenzoates (8) 88%. It was possible to recover, in good amount and from all the reactions, o-benzenedisulfonimide (9), reusable for the preparation of salts 1.