130-03-0

Basic information

• Product Name: 1-BENZOTHIOPHEN-3(2H)-ONE
• Synonyms: 1-BENZOTHIOPHEN-3(2H)-ONE;1-BENZOTHIOPHEN-3-OL;benzo[b]thiophen-3(2H)-one;2,3-dihydro-1-benzothiophen-3-one
• CAS NO: 130-03-0
• Molecular Formula: C₈H₆OS
• Molecular Weight: 150.2
• Mol File: 130-03-0.mol
• Article Data: 24

Chemical Properties

• Melting Point: 230 °C
• Boiling Point: 273.393 °C at 760 mmHg
• Flash Point: 143.683 °C
• Appearance: /
• Density: 1.312 g/cm³
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.657
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• CAS DataBase Reference: 1-BENZOTHIOPHEN-3(2H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZOTHIOPHEN-3(2H)-ONE(130-03-0)
• EPA Substance Registry System: 1-BENZOTHIOPHEN-3(2H)-ONE(130-03-0)

Safety Data

• Hazardous Substances Data: 130-03-0(Hazardous Substances Data)

Usage

Uses

1-benzothiophene-3 (2H) - one is an organic intermediate, which can be prepared from 2-carboxymethyl thiobenzoic acid as starting material. It can be used to prepare fluorescent red 5B. Fluorescent red 5b is an oil-soluble solvent pigment with blue light, which has good heat resistance, light resistance, high coloring power and bright color; It can be used for coloring a variety of resins.

Synthesis Reference(s)

The Journal of Organic Chemistry, 10, p. 381, 1945 DOI: 10.1021/jo01181a001

InChI:InChI=1/C8H6OS/c9-7-5-10-8-4-2-1-3-6(7)8/h1-4H,5H2

Upstream product

• 98589-44-7 (2-cyano-phenylsulfanyl)-acetic acid 
• 3724-10-5 2-(methylthio)benzoic acid 
• 520-72-9 3-hydroxybenzothiophene 
• 7031-27-8 (phenylthio)acetic acid chloride 
• 71-43-2 benzene 
• 108-98-5 thiophenol 
• 7342-82-7 3-Bromothianaphthene 
• 28800-49-9 tris((3-benzo{b}thienyl)boroxine)Tris((3-benzo{b}thienyl)boroxin) 
• 7722-84-1 dihydrogen peroxide 
• 4209-25-0 2-chloro-1-(2-chlorophenyl)ethanone 
• 17333-86-7 o-Carboxybenzenediazonium 
• 147-93-3 Thiosalicylic acid 
• 16671-86-6 2-thiocyanatobenzoic acid 
• 65-85-0 benzoic acid 

Downstream Products

• 5076-82-4 sarcosine anhydride 
• 85869-47-2 N-(<1>benzothienyl-3) sarcosinate d'ethyle 
• 520-72-9 3-hydroxybenzothiophene 
• 23086-31-9 2-(1-methylethylidene)-1-benzothiophen-3-(2H)-one 
• 15051-71-5 6,6-dimethyl-6H-di<1>benzothieno<3,2-b:2,3-e>pyran 
• 95-15-8 Benzo[b]thiophene 
• 10135-00-9 3-bromobenzo[b]thiophene-2-carbaldehyde 
• 101000-97-9 (Z)-2-(4-bromobenzylidene)benzo[b]thiophen-3(2H)-one 
• 63329-72-6 (Z)-2-benzylidenebenzo[b]thiophen-3(2H)-one 
• 62786-15-6 2-benzylidene-1-benzothiophen-3(2H)-one 
• 97871-93-7 (Z)-2-(4-methylbenzylidene)benzo[b]thiophen-3(2H)-one 
• 101000-95-7 (Z)-2-(4-methoxybenzylidene)benzo[b]thiophen-3(2H)-one 

Relevant articles and documents

γ-Radiolysis of Aqueous Benzothiophene Solutions

γ-Radiolysis of aqueous benzothiophene solutions saturated with N2O has been studied.In the absence of other reagents, the only products detected are 2- and 3-hydroxybenzothiophene and their corresponding lactonic and ketonic tautomers and a small amount of dimeric species.In the presence of potassium hexacyanoferrate or sodium hydroxide, however, products attributable to hydroxylation at all six available carbon sites are detected and dimer formation is reduced.Analysis of the experimental data suggests that both benzothiophene and its hydroxylation products are efficient scavengers for the radiation-produced OH radicals and that the initial yield of hydroxylation products is equal to that of hydroxyl radicals.Consistent with the electrophilic characteristics of the OH radical, k(OH+C8H6S):k(OH+C8H5SOH)=0.5+/-0.1.All six available carbon sites are capable of forming OH adducts, but the radicals formed by addition to the 4, 5, 6, and 7 positions tend to revert to the original compound or its ion in a neutral or acidic medium.In the case of the adducts formed by addition to the thiophene ring, on the other hand, the 3 position is seen to be favored, possibly as the result of the preservation of the aromatic benzene resonance structure.

Fused thiopyrones, VI: 2-acyl-thiopyrones from 1-indanone, 3-cumaranone, and thioindoxyle

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Integrated Synthesis of Thienyl Thioethers and Thieno[3,2-b]thiophenes via 1-Benzothiophen-3(2 H)-ones

A one-pot procedure for the synthesis of thienyl thioethers is described. Several thienyl thioethers were synthesized by a TfOH-promoted Friedel-Crafts-type cyclization, a subsequent nucleophilic attack by an arenethiol, and dehydration. This protocol was

Twisted Hemithioindigo Photoswitches: Solvent Polarity Determines the Type of Light-Induced Rotations

Controlling the internal motions of molecules by outside stimuli is a decisive task for the generation of responsive and complex molecular behavior and functionality. Light-induced structural changes of photoswitches are of special high interest due to the ease of signal application and high repeatability. Typically photoswitches use one reaction coordinate in their switching process and change between two more or less-defined states. Here we report on new twisted hemithioindigo photoswitches enabling two different reaction coordinates to be used for the switching process. Depending on the polarity of the solvent, either complete single bond (in DMSO) or double bond (in cyclohexane) rotation can be induced by visible light. This mutually independent switching establishes an unprecedented two-dimensional control of intramolecular rotations in this class of photoswitches. The mechanistic explanation involves formation of highly polar twisted intramolecular charge-transfer species in the excited state and is based on a large body of experimental quantifications, most notably ultrafast spectroscopy and quantum yield measurements in solvents of different polarity. The concept of pre-twisting in the ground state to open new, independent reaction coordinates in the excited state should be transferable to other photoswitching systems.