1,3-Dihydrobenzo[c]thiophene 2,2-dioxide

Base Information

• Chemical Name: 1,3-Dihydrobenzo[c]thiophene 2,2-dioxide
• CAS No.: 2471-91-2
• Molecular Formula: C8H8 O2 S
• Molecular Weight: 168.216
• Hs Code.: 2934999090
• Mol file: 2471-91-2.mol

Synonyms:1,3-Dihydro-2-benzothiophene2,2-dioxide; 1,3-Dihydrobenzo[c]thiophene 2,2-dioxide;1,3-Dihydroisothianaphthene 2,2-dioxide; 2-Thiaindan sulfone; NSC 229311

Chemical Property of 1,3-Dihydrobenzo[c]thiophene 2,2-dioxide

Chemical Property:

• Vapor Pressure: 6.8E-06mmHg at 25°C
• Boiling Point: 388.6°Cat760mmHg
• Flash Point: 259.3°C
• PSA: 42.52000
• Density: 1.344g/cm³
• LogP: 2.19580

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,3-Dihydrobenzo[c]thiophene 2,2-dioxide

There total 4 articles about 1,3-Dihydrobenzo[c]thiophene 2,2-dioxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 20.5%

norborn-2-ene (498-66-8) + α,α'-dibromo-o-xylene (91-13-4) → 1,3-dihydrobenzo[c]thiophene-2,2-dioxide (2471-91-2) + 1,4-dihydro-2,3-benzoxathiin 3-oxide (51439-46-4) + C6H4(CH2)2C7H10 (67341-99-5)

Guidance literature:

With rongalite; potassium hydrogencarbonate; In water; N,N-dimethyl-formamide; at 50 ℃; for 28h;

DOI:10.1021/jo00259a026

Reference yield:

1,3-Dihydrobenzothiophen (2471-92-3) → syn- and anti-cis-8-thiabicyclo<4.3.0>non-3-ene 8-oxide (3533-72-0) + 1,3-dihydrobenzo[c]thiophene-2,2-dioxide (2471-91-2)

Guidance literature:

With chloro[5,10,15,20-tetrakis(4-dimethylamino-2,3,5,6-tetrafluorophenyl)porphyrinate]iron(III); dihydrogen peroxide; In ethanol; water; at 22 - 25 ℃; for 1.5h; chemoselective reaction; Darkness; Green chemistry;

DOI:10.1016/j.catcom.2014.06.032

Reference yield:

1-hydroxy-1,3-dihydrobenzothiophene-2,2-dioxide (92912-33-9) → 1,3-dihydrobenzo[c]thiophene-2,2-dioxide (2471-91-2) + 1,4-dihydro-2,3-benzoxathiin 3-oxide (51439-46-4)

Guidance literature:

With hydrogenchloride; sodium tetrahydroborate; Yield given. Multistep reaction; 1.) methanol, 0 deg C, 30 min; 2.) 50 deg C, 5 min;

DOI:10.1016/S0040-4039(01)81585-9

upstream raw materials:

1-hydroxy-1,3-dihydrobenzothiophene-2,2-dioxide

norborn-2-ene

α,α'-dibromo-o-xylene

1,4-dihydro-2,3-benzoxathiin 3-oxide

Downstream raw materials:

2-phenyl-(3ar,9ac)-3a,4,9,9a-tetrahydro-benz[f]isoindole-1,3-dione

o-xylene

benzocyclobutene

5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene

Refernces

New Benzo[b]xanthones from Diels-Alder Reactions of Chromone-3- carboxaldehydes with ortho-Benzoquinodimethanes

10.1007/s00706-002-0567-7

The study focuses on the synthesis of new benzo[b]xanthone derivatives, which are polyphenolic heterocyclic compounds with potential biological properties. The researchers utilized chromone-3-carboxaldehydes and ortho-benzoquinodimethanes in Diels-Alder reactions to produce these derivatives, with the latter generated in situ from 1,3-dihydrobenzo[c]thiophene 2,2-dioxides. The purpose of these chemicals was to create novel benzo[b]xanthones bearing substituents in the A and D rings through a series of cycloaddition reactions and subsequent oxidations. The synthesized compounds were characterized using various analytical techniques such as 1D and 2D NMR, MS, and elemental analysis, with the stereochemistry of the diastereomeric cycloadducts established by NOESY experiments.

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