Benzothiophene

Benzothiophene[1][2]
IUPAC name Benzo[b]thiophene
Other names 1-Benzothiophene Thianaphthene Benzothiofuran
Identifiers
CAS number	95-15-8 Y
ChemSpider	6951 Y
ChEBI	CHEBI:35858 Y
ChEMBL	CHEMBL87112 Y
RTECS number	202-395-7
Jmol-3D images	Image 1
SMILES s2c1ccccc1cc2
InChI InChI=1S/C8H6S/c1-2-4-8-7(3-1)5-6-9-8/h1-6H Y Key: FCEHBMOGCRZNNI-UHFFFAOYSA-N Y InChI=1/C8H6S/c1-2-4-8-7(3-1)5-6-9-8/h1-6H Key: FCEHBMOGCRZNNI-UHFFFAOYAI
Properties
Molecular formula	C8H6S
Molar mass	134.20 g mol−1
Appearance	White solid
Density	1.15 g/cm3
Melting point	32 °C; 90 °F; 305 K
Boiling point	221 °C; 430 °F; 494 K
Hazards
R-phrases	R22
S-phrases	S22 S24/25
Flash point	110 °C; 230 °F; 383 K
Related compounds
Related compounds	Thiophene Indole Benzofuran
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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. It is used primarily in industry and research.

Being a heterocyclic compound, 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.

Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.

References