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.
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||134.20 g·mol−1|
|Melting point||32 °C (90 °F; 305 K)|
|Boiling point||221 °C (430 °F; 494 K)|
|GHS Signal word||Warning|
|P264, P270, P273, P301+312, P330, P391, P501|
|Flash point||110 °C (230 °F; 383 K)|
Indene, Benzofuran, Indole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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.
- Merck Index, 11th Edition, 9232
- |FLUKA&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC 1-Benzothiophene at Sigma-Aldrich
- Cava, Michael P.; Lakshmikantham, M. V. (1975). "Nonclassical Condensed Thiophenes". Accounts of Chemical Research. 8: 139–44. doi:10.1021/ar50088a005.CS1 maint: uses authors parameter (link)