2,4-Dithiapentane is an organosulfur compound, and is the simplest alkyl dithioether. It is a colorless liquid with a strong odor, reminiscent of freshly prepared mustard in the pure form.[1]
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| Names | |
|---|---|
| Preferred IUPAC name Bis(methylsulfanyl)methane | |
| Other names Bis(methylthio)methane Bis(methylmercapto)methane 2,4-Dithiapentane | |
| Identifiers | |
3D model (JSmol) | |
| 1731143 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.015.071 |
| EC Number |
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PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C3H8S2 | |
| Molar mass | 108.22 g·mol−1 |
| Appearance | Liquid |
| Density | 1.059 g/cm3, liquid |
| Melting point | −20.5 °C (−4.9 °F; 252.7 K) |
| Boiling point | 147 °C (297 °F; 420 K) |
| Immiscible | |
Refractive index (nD) | 1.53 |
| Viscosity | 0.00113 Pa s |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H226, H315, H319, H335 | |
| P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 43.89 °C (111.00 °F; 317.04 K) |
| Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
2,4-Dithiapentane is the dimethyldithioacetal of formaldehyde. Its synthesis was first reported in 1941.[1][2] It is industrially prepared by the acid-catalyzed condensation of methyl mercaptan with formaldehyde.
- 2 CH3SH + H2C=O → CH3SCH2SCH3 + H2O
2,4-Dithiapentane is found as an aromatic component in some truffle varieties.[3][4][5] A synthetic version is used as the primary aromatic additive in commercial "truffle" products, such as truffle oil, truffle butter, truffle salt and truffle pastes, many of which contain no truffle content at all,[6][7] and have elevated levels of 2,4-dithiapentane compared to levels in natural truffle products.[8] It has also been found to occur naturally in rotting wood of some species in the genus Lecythis.[9]