Thiophene

Thiophene
Full displayed formula of thiophene
Full displayed formula of thiophene
Skeletal formula showing numbering convention
Skeletal formula showing numbering convention
Ball-and-stick model
Ball-and-stick model
Space-filling model
Space-filling model
Names
Preferred IUPAC name
Thiophene[1]
Other names
Thiofuran
Thiacyclopentadiene
Thiole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.392 Edit this at Wikidata
RTECS number
  • XM7350000
UNII
  • InChI=1S/C4H4S/c1-2-4-5-3-1/h1-4H checkY
    Key: YTPLMLYBLZKORZ-UHFFFAOYSA-N checkY
  • InChI=1/C4H4S/c1-2-4-5-3-1/h1-4H
    Key: YTPLMLYBLZKORZ-UHFFFAOYAY
  • c1ccsc1
Properties
C4H4S
Molar mass 84.14 g/mol
Appearance colorless liquid
Density 1.051 g/mL, liquid
Melting point −38 °C (−36 °F; 235 K)
Boiling point 84 °C (183 °F; 357 K)
-57.38·10−6 cm3/mol
1.5287
Viscosity 0.8712 cP at 0.2 °C
0.6432 cP at 22.4 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
GHS labelling:[2]
GHS02: FlammableGHS07: Exclamation mark
Danger
H225, H302, H319, H412
P210, P260, P262, P273, P305+P351+P338, P403+P235
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Flash point −1 °C (30 °F; 272 K)
Safety data sheet (SDS) External MSDS, External MSDS
Related compounds
Related thioethers
 Tetrahydrothiophene
Diethyl sulfide
Related compounds
 Furan
Selenophene
Pyrrole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reactions, it resembles benzene. Compounds analogous to thiophene include furan (C4H4O), selenophene (C4H4Se) and pyrrole (C4H4NH), which each vary by the heteroatom in the ring.

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 141. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ GHS: GESTIS 010090