Thiophene
 Sample of old thiophene
| |
| Names | |
|---|---|
| IUPAC name
Thiophene
| |
| Other names
Thiacyclopentadiene
Thiofuran Thiole Thiophen | |
| Properties | |
| C4H4S | |
| Molar mass | 84.14 g/mol |
| Appearance | Colorless liquid |
| Odor | Aromatic, benzene-like |
| Density | 1.06494 g/cm3 (20 °C) 1.051 g/cm3 (25 °C) |
| Melting point | −38 °C (−36 °F; 235 K) |
| Boiling point | 84 °C (183 °F; 357 K) |
| 0.301 g/100 ml (25 °C) | |
| Solubility | Miscible glacial acetic acid, acetone, benzene, carbon tetrachloride, diethyl ether, dioxane, ethanol, isopropanol, pyridine, toluene, xylene |
| Vapor pressure | 40 mmHg (12.5 °C) |
| Thermochemistry | |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | −1 °C (30 °F; 272 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
1,400 mg/kg (rat, oral) |
| Related compounds | |
| Related compounds
|
Furan |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Thiophene is a heterocyclic compound with the formula C4H4S. It is the sulfur analogue of furan.
Thiophene is considered to be aromatic, although theoretical calculations suggest that the degree of aromaticity is less than that of benzene. The "electron pairs" on sulfur are significantly delocalized in the pi electron system.
Contents
Properties
Chemical
Oxidation of thiophene with trifluoroperacetic acid gives thiophene S-oxide.
Desulfurization of thiophene with Raney nickel yields butane.
Physical
Thiophene is a colorless liquid, with an odor similar to benzene. Older samples appear darker in color.
Availability
Thiophene is sold by lab suppliers.
Preparation
Can be prepared by reacting diacetylene with sodium sulfide, with KOH, using DMSO as solvent.[1]
Projects
- Make thiophene S-oxide
Handling
Safety
Thiophene is harmful and irritant if inhaled. It is flammable, and combustion will yield sulfur dioxide which is a strong irritant.
Storage
In closed bottles, in dark, away from light.
Disposal
Should be burned in a special incinerator or neutralized with Fenton's reagent.
