2,4-Dithiapentane

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]

2,4-Dithiapentane

Names
Preferred IUPAC name Bis(methylsulfanyl)methane
Other names Bis(methylthio)methane Bis(methylmercapto)methane 2,4-Dithiapentane
Identifiers
CAS Number	1618-26-4 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1731143
ChEBI	CHEBI:167064
ChemSpider	14639 Y
ECHA InfoCard	100.015.071
EC Number	216-577-9
PubChem CID	15380
UNII	128SGX814T Y
CompTox Dashboard (EPA)	DTXSID0061822
InChI InChI=1S/C3H8S2/c1-4-3-5-2/h3H2,1-2H3 Y Key: LOCDPORVFVOGCR-UHFFFAOYSA-N Y InChI=1/C3H8S2/c1-4-3-5-2/h3H2,1-2H3 Key: LOCDPORVFVOGCR-UHFFFAOYAH
SMILES CSCSC
Properties
Chemical formula	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)
Solubility in water	Immiscible
Refractive index (nD)	1.53
Viscosity	0.00113 Pa s
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H315, H319, H335
Precautionary statements	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)	1 2
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). N verify (what is YN ?) Infobox references

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, the main aromatic compound in both halitosis and foot odor and a secondary compound in flatulence,^[3] with formaldehyde.

2 CH₃SH + H₂C=O → CH₃SCH₂SCH₃ + H₂O

2,4-Dithiapentane is found as an aromatic component in some truffle varieties.^[4][5][6] 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,^[7][8] and have elevated levels of 2,4-dithiapentane compared to levels in natural truffle products.^[9] It has also been found to occur naturally in rotting wood of some species in the genus Lecythis.^[10]

Notes and references

1. "2,4-Dithiapentane". American Chemical Society. Retrieved 3 April 2024.
2. Böhme, Horst; Marx, Robert (8 October 1941). "Zur Kenntnis der Trisulfonyl-methane". Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 74 (10): 1667–1675. doi:10.1002/cber.19410741009. Retrieved 3 April 2024.
3. "The Chemistry of Body Odours". Compound Interest. 7 April 2014.
4. A. Fiecchi; M. Galli Kienle; A. Scala & P. Cabella (1967). "Bis-methylthiomethane, an odorous substance from white truffle, tuber magnatum pico". Tetrahedron Lett. 18: 1681–1682. doi:10.1016/S0040-4039(00)90698-1.
5. Franco Bellesia; Adriano Pinetti; Alberto Bianchi and Bruno Tirillini (1996). "Volatile Compounds of the White Truffle (Tuber magnatum Pico) from Middle Italy". Flavour and Fragrance Journal. 11 (4): 239–243. doi:10.1002/(SICI)1099-1026(199607)11:4<239::AID-FFJ573>3.0.CO;2-A.
6. Richard Splivallo & Susan E. Ebeler (2015). "Sulfur volatiles of microbial origin are key contributors to human-sensed truffle aroma". Biotechnological Products and Process Engineering: Applied Microbiology and Biotechnology. 99 (6): 2583–2592. doi:10.1007/s00253-014-6360-9. PMID 25573471. S2CID 16749990.
7. Patterson, Daniel (2007-05-16). "Hocus-Pocus, and a Beaker of Truffles". The New York Times. Retrieved 2008-02-13.
8. Babich, Matt (July 12, 2022). "The truffle industry is a big scam. Not just truffle oil, everything". www.tasteatlas.com. Retrieved 2022-11-19.
9. Paul Thomas; Waill Elkhateeb; Ghoson Daba (2021). "Industrial Applications of Truffles and Truffle-like Fungi". In Kandikere R. Sridhar; Sunil K. Deshmukh (eds.). Advances in Macrofungi. CRC Press. ISBN 978-1-003-09681-8. Retrieved 3 April 2024.
10. Amy Berkov; Barbara Meurer-Grimes; Kenneth L. Purzycki (2000). "Do Lecythidaceae Specialists (Coleoptera, Cerambycidae) Shun Fetid Tree Species?". Biotropica. 32 (3): 440–451. doi:10.1646/0006-3606(2000)032[0440:dlsccs]2.0.co;2. S2CID 198156552.