5698-59-9

Basic information

• Product Name: 1,3-Dihydro-2-benzothiophene-1,3-dione
• Synonyms: 1,3-Dihydro-2-benzothiophene-1,3-dione;Benzo[c]thiophene-1,3-dione;Phthalic thioanhydride;Thiophthalic anhydride
• CAS NO: 5698-59-9
• Molecular Formula: C₈H₄O₂S
• Molecular Weight: 164.1812
• Mol File: 5698-59-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 338°Cat760mmHg
• Flash Point: 163°C
• Appearance: /
• Density: 1.479g/cm³
• Vapor Pressure: 0.000101mmHg at 25°C
• Refractive Index: 1.686
• CAS DataBase Reference: 1,3-Dihydro-2-benzothiophene-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dihydro-2-benzothiophene-1,3-dione(5698-59-9)
• EPA Substance Registry System: 1,3-Dihydro-2-benzothiophene-1,3-dione(5698-59-9)

Safety Data

• Hazardous Substances Data: 5698-59-9(Hazardous Substances Data)

Usage

General Description

1,3-Dihydro-2-benzothiophene-1,3-dione, also known as benzothiophenedione, is a chemical compound with the molecular formula C8H6O2S. It is a bicyclic heteroaromatic compound that contains both a benzene ring and a thiophene ring, and is often used as an intermediate in the synthesis of various organic compounds. Benzothiophenedione has been studied for its potential use in pharmaceuticals, as it exhibits antioxidant and anticancer properties. It is also used in the production of dyes, pigments, and other specialty chemicals. However, it is important to handle this compound with care, as it may be harmful if ingested, inhaled, or absorbed through the skin.

InChI:InChI=1/C8H4O2S/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4H

Upstream product

• 93097-85-9 di-O-isopropyl-S,S-phthaloyl dixanthate (unsymmetrical) 
• 85-44-9 phthalic anhydride 

Downstream Products

• 409108-76-5 thiophthalic acid-2-ethyl ester 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 3878-45-3 triphenylphosphine sulfide 
• 23667-32-5 trans-dithiobiphthalide 
• 26257-08-9 methanethiol 
• 42211-56-3 (±)-3-benzyl-3-hydroxybenzo[c]thiophen-1(3H)-one 
• 22751-52-6 2,3-diphenylbenzo[b]thiophene 
• 1276032-21-3 3,4-diphenyl-1H-isothiochromen-1-one 
• 1276032-32-6 2,3-diphenyl-4H-thiochromen-4-one 
• 1276032-36-0 2-(4-methoxyphenyl)-3-(4-(trifluoromethyl)phenyl)-4H-thiochromen-4-one 
• 1276032-49-5 3-(4-methoxyphenyl)-2-(4-(trifluoromethyl)phenyl)-4H-thiochromen-4-one 
• 1276032-47-3 2-(4-methoxyphenyl)-3-(4-(trifluoromethyl)phenyl)benzo[b]thiophene 
• 1276032-31-5 3-(4-methoxyphenyl)-2-(4-(trifluoromethyl)phenyl)benzo[b]thiophene 
• 1276032-43-9 3-(4-methoxyphenyl)-4-(4-(trifluoromethyl)phenyl)-1H-isothiochromene-1-one 

Relevant articles and documents

Optical absorption spectra of aromatic isothianaphthene oligomers. Theory and experiment

We investigate the optical absorption spectra of aromatic isothianaphthene oligomers, from the monomer up to the tetramer, with a combined theoretical and experimental approach. Geometry optimizations are performed with the semiempirical Austin model 1 method on disilylated isothianaphthene oligomers of increasing chain length. The calculated geometric parameters are compared to those obtained from the single-crystal structure of the 3,3′-bis(tert-butyldimethylsilyl)-1,1′-biisothianaphthene. We then use the intermediate neglect of differential overlap method, coupled to single configuration interaction, to simulate theoretically the optical absorption spectra of the oligomers. The corresponding experimental spectra are recorded in n-hexane solution and their evolution with chain length is discussed on the basis of the theoretical data.

Multiple-State Emissions from Neat, Single-Component Molecular Solids: Suppression of Kasha's Rule

Three rigid and structurally simple heterocyclic stilbene derivatives, (E)-3H,3′H-[1,1′-biisobenzofuranylidene]-3,3′-dione, (E)-3-(3-oxobenzo[c] thiophen-1(3H)-ylidene)isobenzofuran-1(3H)-one, and (E)-3H,3′H-[1,1′-bibenzo[c] thiophenylidene]-3,3′-dione, are found to fluoresce in their neat solid phases, from upper (S2) and lowest (S1) singlet excited states, even at room temperature in air. Photophysical studies, single-crystal structures, and theoretical calculations indicate that large energy gaps between S2 and S1 states (T2 and T1 states) as well as an abundance of intra and intermolecular hydrogen bonds suppress internal conversions of the upper excited states in the solids and make possible the fluorescence from S2 excited states (phosphorescence from T2 excited states). These results, including unprecedented fluorescence quantum yields (2.3–9.6 %) from the S2 states in the neat solids, establish a unique molecular skeleton for achieving multi-colored emissions from upper excited states by “suppressing” Kasha's rule.

Indium-catalyzed direct conversion of lactones into thiolactones using a disilathiane as a sulfur source

An indium-catalyzed reaction of lactones and a disilathiane leading to thiolactones is described. The direct synthesis of thiolactones from lactones with an appropriate sulfur source is one of the most attractive approaches in organic and pharmaceutical chemistry. In this context, we found an indium-catalyzed direct conversion of lactones into thiolactones in the presence of elemental sulfur and a hydrosilane via formation of the disilathiane in situ. On the basis of the previous reaction, the application utilizing the disilathiane as a sulfur source was performed herein for the efficient synthesis of a variety of thiolactone derivatives from lactones by an indium catalyst.