2471-91-2

Basic information

• Product Name: 1,3-Dihydrobenzo[c]thiophene 2,2-dioxide
• Synonyms: 1,3-Dihydrobenzo[c]thiophene 2,2-dioxide
• CAS NO: 2471-91-2
• Molecular Formula: C₈H₈O₂S
• Molecular Weight: 168.2129
• Mol File: 2471-91-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 388.6°Cat760mmHg
• Flash Point: 259.3°C
• Appearance: /
• Density: 1.344g/cm³
• Vapor Pressure: 6.8E-06mmHg at 25°C
• Refractive Index: 1.599
• CAS DataBase Reference: 1,3-Dihydrobenzo[c]thiophene 2,2-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dihydrobenzo[c]thiophene 2,2-dioxide(2471-91-2)
• EPA Substance Registry System: 1,3-Dihydrobenzo[c]thiophene 2,2-dioxide(2471-91-2)

Safety Data

• Hazardous Substances Data: 2471-91-2(Hazardous Substances Data)

Usage

Heterocyclic organic compound

Contains a benzene ring fused to a thiophene ring and two oxygen atoms.

Used in the synthesis of pharmaceuticals and agrochemicals

Due to its unique structure and properties.
The compound's structure allows it to be a versatile building block for creating various pharmaceuticals and agrochemicals.

Potential application in organic light-emitting diodes (OLEDs)

As a building block for the synthesis of new materials.
The compound's electronic properties make it a candidate for use in the development of OLEDs, which are used in display technologies and lighting.

Researched for potential biological activities and therapeutic applications

Due to its unique structure and properties.
The compound's structure and properties are being investigated for possible applications in the field of biology and medicine, including potential therapeutic uses.

Chemical stability

The presence of the benzene and thiophene rings, along with the oxygen atoms, contributes to the compound's stability.
The fused benzene and thiophene rings, along with the oxygen atoms, provide a stable structure that can be useful in various applications.

Solubility

The compound is likely to be soluble in organic solvents such as ethanol, methanol, and acetone.
Due to its organic nature, 1,3-Dihydrobenzo[c]thiophene 2,2-dioxide is expected to dissolve in common organic solvents, which is important for its use in chemical reactions and synthesis.

Reactivity

The compound may undergo various chemical reactions, such as electrophilic aromatic substitution, nucleophilic substitution, and oxidation reactions.
The presence of the benzene and thiophene rings in the molecule makes it susceptible to a range of chemical reactions, which can be exploited for the synthesis of new compounds and materials.

InChI:InChI=1/C8H8O2S/c9-11(10)5-7-3-1-2-4-8(7)6-11/h1-4H,5-6H2

Upstream product

• 2471-92-3 1,3-Dihydrobenzothiophen 
• 51439-46-4 1,4-dihydro-2,3-benzoxathiin 3-oxide 
• 498-66-8 norborn-2-ene 
• 91-13-4 α,α'-dibromo-o-xylene 
• 92912-33-9 1-hydroxy-1,3-dihydrobenzothiophene-2,2-dioxide 

Downstream Products

• 102028-26-2 2-phenyl-(3ar,9ac)-3a,4,9,9a-tetrahydro-benz[f]isoindole-1,3-dione 
• 95-47-6 o-xylene 
• 694-87-1 benzocyclobutene 
• 1460-59-9 5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene 
• 72413-05-9 α-(benzoylamino)-1,3-dihydrobenzothiophene-5-acetic acid 2,2-dioxide 
• 79265-87-5 1-benzyl-1,3-dihydrobenzothiophen 2,2-dioxide 
• 32796-95-5 1,2-dimethylenebenzene 

Relevant articles and documents

A green and sustainable method for the oxidation of 1,3-dihydrobenzo[c] thiophenes to sulfones using metalloporphyrin complexes

Two efficient methods are reported for the oxidation of 1,3-dihydrobenzo[c]thiophenes to sulfones in good to high yields using H 2O2 in the presence of catalytic amounts of porphyrin-based catalysts in ethanol or acetonitrile as solvents at room temperature. The presence of electron-donating or electron-withdrawing groups, in the benzene ring of 1,3-dihydrobenzo[c]thiophene, is well tolerated.

Organic Reactions of Reduced Species of Sulfur Dioxide

Rongalite (sodium hydroxymethanesulfinate or sodium formaldehydesulfoxylate) reacts with organic halides in a variety of ways depending on the structure of the organic compound.Benzyl and other alkyl halides give sulfones in generally good yields; but in several cases, reduction (2,4-dinitrobenzyl bromide, phenacyl halides) or coupling (p-nitrobenzyl bromide under basic conditions, phenacyl bromide or iodide) of the halide occurs.Addition of sodium iodide to the mixture of Rongalite and phenacyl chloride changed the reaction from one of complete reduction to acetophenone to one of mainly dimerization to 1,4-diphenyl-1,4-butanedione.The amount of acetophenone from phenacyl bromide depends on the water content of the reaction mixture, more dimer being formed when little water is present.Diphenacyl sulfone is formed from phenacyl bromide and Rongalite in the presence of excess sulfur dioxide.The intermediate β-keto sulfinate is believed to normally lose sulfur dioxide very readily to give the enolate anion, which either is protonated to give acetophenone or reacts with phenacyl halide to give the butanedione.In the presence of excess sulfur dioxide, the loss of sulfur dioxide from the sulfinate is supressed, allowing sulfone formation to occur by reaction of the sulfinate with phenacyl halide. o-Xylylene dibromide gave o-xylylene, trapped as the Diels-Alder adduct with norbornene, along with the expected cyclic sulfone and cyclic sulfinate ester (sultine).A convenient synthesis of the sultine in 78percent yield is achieved by treatment of α,α'-dichloro-o-xylene with Rongalite and sodium iodide.Treatment of Rongalite in DMF-H2O with sulfur dioxide gives the blue anion radical complex (SO2)(SO2.-).Anion radicals are produced from p-dinitrobenzene and p-nitrobenzoate ion when they are treated with Rongalite.