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Benzothiophene

Aromatic organic compound

Benzothiophene
Summary

Aromatic organic compound

Thianaphthene Benzothiofuran Indene, Benzofuran, Indole

Benzothiophene is an aromatic organic compound with a molecular formula C8H6S and an odor similar to naphthalene (mothballs). It occurs naturally as a constituent of petroleum-related deposits such as lignite tar. Benzothiophene has no household use. In addition to benzo[b]thiophene, a second isomer is known: benzo[c]thiophene.

Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP. It is also used in the manufacturing of dyes such as thioindigo.

Synthesis

Most syntheses of benzothiophene create substituted benzothiophenes as a precursor to further reactions. An example is the reaction of an alkyne-substituted 2-bromobenzene with either sodium sulfide or potassium sulfide to form benzothiophene with an alkyl substitution at position 2.

Thiourea can be used as a reagent in place of sodium sulfide or potassium sulfide.

In the presence of a gold catalyst, a more complex 2,3-disubstituted benzothiophene can be synthesised.

References

References

  1. [[Merck Index]], 11th Edition, '''9232'''
  2. "Thianaphthene". [[Sigma Aldrich]].
  3. (1975). "Nonclassical Condensed Thiophenes". Accounts of Chemical Research.
  4. (16 September 2011). "CuI/TMEDA-Catalyzed Annulation of 2-Bromo Alkynylbenzenes with Na2S: Synthesis of Benzo[b]thiophenes". American Chemical Society (ACS).
  5. (5 August 2011). "Palladium-Catalyzed C–S Coupling: Access to Thioethers, Benzo[b]thiophenes, and Thieno[3,2-b]thiophenes". American Chemical Society (ACS).
  6. (3 July 2006). "Gold-Catalyzed Intramolecular Carbothiolation of Alkynes: Synthesis of 2,3-Disubstituted Benzothiophenes from (α-Alkoxy Alkyl) (ortho-Alkynyl Phenyl) Sulfides". Wiley.
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benzothiophenes simple-aromatic-rings
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