Benzothiophene

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Structural formula
Structure of benzothiophene
General
Surname Benzothiophene
other names
  • 1-benzothiophene
  • Benzo [ b ] thiophene
  • Thianaphthene
  • 1-thiainden
  • 2,3-benzothiophene
  • Benzothiofuran
Molecular formula C 8 H 6 S
Brief description

white, flammable solid with an unpleasant odor

External identifiers / databases
CAS number 95-15-8
EC number 202-395-7
ECHA InfoCard 100.002.178
PubChem 7221
Wikidata Q419709
properties
Molar mass 134.20 g mol −1
Physical state

firmly

density

1.1486 g cm −3 (36 ° C )

Melting point

28-32 ° C

boiling point

222 ° C

Vapor pressure

1.33 h Pa (20 ° C)

solubility
  • heavy in water (0.13 g l −1 at 25 ° C)
  • good in organic solvents
Refractive index

1.6374 (37 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 302-411
P: 273
Toxicological data

1700 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Benzothiophene is a chemical compound whose structure consists of a thiophene ring and a fused benzene ring . This bicyclic heteroaromatic is the basic structure of many derivatives for a wide range of applications in the chemical industry, especially in the pharmaceutical and dye industry, such as for example for insecticides, pesticides, thioindigo and pharmaceuticals such as raloxifene , zileuton and sertaconazole .

Occurrence

Benzothiophene naturally occurs in small quantities in petroleum, heating and heavy oils.

properties

Benzothiophene is a white, flammable solid with an unpleasant odor, which is sparingly soluble in water. It has a refractive index of 1.63 (at 37 ° C). In medicinal chemistry, benzothiophene isostere can be replaced by naphthalene.

Related links

Individual evidence

  1. ↑ a b c d e f Entry on thionaphthene in the GESTIS substance database of the IFA , accessed on February 14, 2017(JavaScript required) .
  2. ↑ a b Brockhaus ABC Chemie , VEB FA Brockhaus Verlag, Leipzig 1965, p. 1411.
  3. ↑ a b Benzothiophene data sheet (PDF) from Merck , accessed on January 18, 2011.
  4. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-40.