1,2-Benzenedithiol
 |
|
 |
|
| Names | |
|---|---|
|
Preferred IUPAC name
Benzene-1,2-dithiol
|
|
| Other names
1,2-Dimercaptobenzene
|
|
| Identifiers | |
|
3D model (JSmol)
|
|
| ChemSpider | |
| ECHA InfoCard | 100.037.740 |
|
PubChem CID
|
|
|
|
|
|
| Properties | |
| C6H6S2 | |
| Molar mass | 142.24 g/mol |
| Appearance | colourless liquid |
| Density | 1.236 g/mL |
| Melting point | 22 to 24 °C (72 to 75 °F; 295 to 297 K) |
| Boiling point | 119 to 120 °C (246 to 248 °F; 392 to 393 K) at 17 mmHg |
| Soluble in basic water | |
| Hazards | |
| Main hazards | stench |
| Flash point | 104.0 °C; 219.2 °F; 377.1 K |
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
|
 (what is   ?) |
|
| Infobox references | |
1,2-Benzenedithiol is the organosulfur compound with the formula C6H4(SH)2. This colourless viscous liquid consists of a benzene ring with a pair of adjacent thiol groups. The conjugate base of this diprotic compound serves as chelating agent in coordination chemistry and a building block for the synthesis of other organosulfur compounds.
The compound is prepared by ortho-lithiation of benzenethiol using butyl lithium (BuLi) followed by sulfidation:
The compound was first prepared from 2-aminobenzenethiol via diazotization. Alternatively, it forms from 1,2-dibromobenzene.
Oxidation mainly affords the polymeric disulfide. Reaction with metal dihalides and metal oxides gives the dithiolate complexes of the formula LnM(S2C6H4) where LnM represents a variety of metal centers, e.g. (C5H5)2Ti. Ketones and aldehydes condense to give the heterocycles called dithianes:
3,4-Toluenedithiol, also called dimercaptotoluene (CAS#496-74-2), behaves similarly to 1,2-benzenedithiol but is a solid at ambient temperatures (m.p. 135-137 °C).
Alkene-1,2-dithiols are unstable, although metal complexes of alkene-1,2-dithiolates, called dithiolene complexes, are well known.
...
Wikipedia