Benzothiophene

Benzothiophene^[1][2]

Names
IUPAC name Benzo[b]thiophene
Other names 1-Benzothiophene Thianaphthene Benzothiofuran
Identifiers
CAS Registry Number	95-15-8 Y
ChEBI	CHEBI:35858 Y
ChEMBL	ChEMBL87112 Y
ChemSpider	6951 Y
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
Jmol-3D images	Image
RTECS number	202-395-7
SMILES s2c1ccccc1cc2
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
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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