THIANAPHTHENE-1,1-DIOXIDE Chemical Properties

Melting point:

138-142 °C

Boiling point:

264.41°C (rough estimate)

Density 

1.3123 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

Powder

Appearance

White to off-white Solid

BRN 

116442

InChI

InChI=1S/C8H6O2S/c9-11(10)6-5-7-3-1-2-4-8(7)11/h1-6H

InChIKey

FRJNKYGTHPUSJR-UHFFFAOYSA-N

SMILES

C12=CC=CC=C1C=CS2(=O)=O

CAS DataBase Reference

825-44-5(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

HS Code 

29309099

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

THIANAPHTHENE-1,1-DIOXIDE Usage And Synthesis

Chemical Properties

White to cream colored powder

Definition

ChEBI: 1H-1lambda~6~-benzo[b]thiophene-1,1-dione is a benzenoid aromatic compound.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 1702, 1949 DOI: 10.1021/ja01173a043

Synthesis

General procedure for the synthesis of benzothiophene sulfone from benzothiophene: 0.15 g (0.0011 mol) of benzothiophene (BT) was placed in a 25 mL round-bottomed flask which was pre-filled with a mixture of 10 mL of toluene/hexane (1:4, v/v) and 0.015 g (0.0135 mmol) of oxidation catalyst. The reaction mixture was heated to 40°C in an oil bath with continuous stirring at 500 rpm. Subsequently, tert-butyl hydroperoxide was added to the reaction system at a molar ratio of oxidizer to substrate of 6.8. The oxidation reaction was carried out under continuous stirring for 6 hours. Upon completion of the reaction, the resulting white benzothiophene sulfone (BTO2) precipitate was collected by filtration and washed with hexane to remove unreacted benzothiophene. The yield was 81%. The 1H NMR (δ, ppm, DMSO-d6) data of the product were as follows: δ 7.83 (d, J = 7.2 Hz, 1H), 7.69 (t, J = 7.4 Hz, 1H), 7.62 (t, J = 9.1 Hz, 3H), 7.34 (d, J = 6.8 Hz, 1H). Elemental analysis results (calculated/measured values, %): C, 57.81/57.49; H, 3.64/3.89; S, 19.29/19.02.

References

[1] Petroleum Chemistry, 2007, vol. 47, # 3, p. 225 - 225
[2] Polyhedron, 2014, vol. 72, p. 19 - 26
[3] RSC Advances, 2014, vol. 4, # 61, p. 32054 - 32062
[4] Patent: CN108658908, 2018, A. Location in patent: Paragraph 0204; 0205
[5] Journal of Organic Chemistry, 1997, vol. 62, # 5, p. 1457 - 1462

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