20133-21-5

Usage

Uses

Used in Rubber Production:
1,2,4,5-Benzenetetrathiol serves as a crosslinking agent in the manufacturing process of rubber, enhancing the material's properties such as strength and elasticity.
Used as a Corrosion Inhibitor:
In industrial applications, 1,2,4,5-Benzenetetrathiol functions as a corrosion inhibitor, protecting metal surfaces from degradation and extending their service life.
Used in Chemical Synthesis:
1,2,4,5-Benzenetetrathiol is utilized in the synthesis of a variety of organic compounds across different sectors. Its applications include the production of dyes, which rely on its chemical properties to achieve specific colorations, and pharmaceuticals, where it may contribute to the development of new drugs.
Additionally, it is employed in the synthesis of antioxidants, which are crucial in various industries to prevent oxidative degradation and extend the shelf life of products.

Upstream product

• 1846-35-1 1,2,4,5-Tetrakis(methylthio)benzene 
• 4115-58-6 1,2,4,5-tetrakis(ethylthio)benzene 
• 447463-65-2 1,2,4,5-tetrakis(tert-butylthio)benzene 
• 74542-69-1 1,2,4,5-Tetrakis(isopropylthio)benzene 
• 95-94-3 1,2,4,5-tetrachlorobenzene 

Downstream Products

• 103088-22-8 benzene-1,2,4,5-tetra(sulfenyl chloride) 

Relevant academic research and scientific papers

Synthesis of Heterocyclic Core-Expanded Bis-Naphthalene Tetracarboxylic Diimides

A highly reactive bis-naphthalene tetracarboxylic diimide (bis-NDI) intermediate, TBrDNDI, was designed and synthesized for core-expanded NDIs. Based on this intermediate, we achieved 9- and 11-membered core-expanded bis-NDI derivatives. Through expanding the NDI core and introducing electron-donor or electron-acceptor groups, the frontier energy orbitals, optical and electrical properties of these bis-NDIs can be finely tuned to obtain air-stable ambipolar or n-type materials.

Fluorescent Dyes with Large Stokes Shifts Based on Benzo[1,2-d:4,5-d']bis([1,3]dithiole) (“S4-DBD Dyes”)

We report on a further development of [1,3]-dioxolo[4.5-f]benzodioxole (DBD) fluorescent dyes by replacement of the four oxygen atoms of the heterocyclic core by sulfur atoms. This variation causes striking changes of the photophysical properties. Whereas absorption and emission significantly shifted to longer wavelength, the fluorescence lifetimes and quantum yields are diminished compared to DBD dyes. The latter effect is presumably caused by an enhanced intersystem crossing to the triplet state due to the sulfur atoms. The very large Stokes shifts of the S4-DBD dyes ranging from 3000 cm–1 to 7400 cm–1 (67 nm to 191 nm) should be especially emphasized. By analogy with DBD dyes a broad variation of absorption and emission wavelength is possible by introducing different electron withdrawing substituents. Moreover, some derivatives for coupling with biomolecules were developed.

Preparation, structure determination, and electrochemical properties of bis{[1,4,8,11, 15,18,22,25-octaethyl-2,3,9,10,16,17,23,24-octakis(methylthio)- phthalocyaninato]titanium(IV)} benzene-1,2,4,5-tetrathiolate

4,5-Bis(methylthio)phthalonitrile 2 was prepared from 2,3,5,6- tetrabromodiethylbenzene in four steps. Tetramerization and cyclization of phthalonitrile 2 with lithium n-pentoxide at 115°C produced octaethyl-octakis(methylthio)phthalocyanine (3). A titanium atom was introduced into the phthalocyanine 3 by treatment with titanium(IV) tetrabutoxide in DMF at 130°C to give the corresponding metal complex 3-TiO. Linking of two molecules of the phthalocyanine 3-TiO with benzene-1,2,4,5-tetrathiol (BTT) produced a double-decker-type compound, bis{[octaethyl-octakis-(methylthio) phthalocyaninato]titanium(IV)} benzenetetrathiolate (6), in which the two phthalocyanines are connected axially through four titanium-sulfur coordination bonds. Double-decker derivative 7 was also obtained by a similar treatment of (tetra-tert-butylphthalocyaninato)titanium(IV) oxide with BTT. The structures of 6 and 7 were determined by NMR, IR, UV/Vis spectroscopy and FAB mass spectrometry. Both phthalocyanine skeletons of 6 have symmetrical structures, as shown by the 1H and 13C NMR spectra. The electrochemical properties of 6 were examined by cyclic voltammetry with Ag/AgNO3 as the reference electrode. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Organo-metal compositions, preparation and use

Complexes of a transition metal and a tetrasubstituted aromatic compound which contain at least two transition metal atoms. At least two of the substituents are -SH groups, the other two substituents being -SH, -OH and -NHR. The complexes are prepared by reacting the tetrasubstituted aromatic compound with a transition metal compound in the presence of a disubstituted aromatic compound. Depending on the relative proportions of the di- and tetra--substituted compounds, the resulting complex may contain more than one residue from the tetra-substituted compound and more than two transition metal atoms. The complexes possess infra-red absorbing properties which vary in dependence on the particular complex, the complexes with more than one residue from the tetrasubstituted compound absorbing radiation of longer wavelength. The compounds can be used to provide infra-red absorbing compositions, for example as a coating or inter-layer for glass. The complexes may be used together with one or more different infra-red absorbing materials. The tetra-substituted aromatic compound may be a tetra-thiol and this can be prepared from an aromatic compound containing at least four halogen substituents by reaction with an alkaline thiol compound in the presence of iron and sulphur in a polar solvent such as dimethyl formamide.

1,2,4,5-TETRAMERCAPTOBENZENE. A Facile Route to the Benzobisdithiole Ring System

The dissolving metal reduction of 1,2,4,5-tetrakis(ethylthio)benzene (2) with alkali metals in various solvents was investigated.Reduction of 2 with lithium in n-propylamine solvent gave 1,2,4,5-Tetramercaptobenzene (1) in high yield.The acid catalysed re

Fragmentation of Aryl Alkyl Sulfides. A Simple, One-Pot Synthesis of Polymercaptobenzenes from Polychlorobenzenes

A simple procedure is described which allows one to prepare polymercaptobenzenes starting from chlorobenzenes.The reactions of all the possible chlorobenzenes with Me2CHSNa in HMPA give the corresponding (isopropylthio)benzenes which can be cleaved by adding sodium to the reaction mixtures to give the arenethiolates in good yields.In some cases the polymercaptobenzenes were isolated after treatment with acid; in other cases methyl iodide was added to the reaction mixture and poly(methylthio)benzenes were obtained.It is suggested that the (isopropylthio)benzenes react with sodium to give the corresponding radical anions which fragment at the sulfur-alkyl bond to give the arenethiolates.