2,4-Dithiapentane

Formula: C₃H₈S₂
Molecular weight: 108.226
IUPAC Standard InChI: InChI=1S/C3H8S2/c1-4-3-5-2/h3H2,1-2H3
IUPAC Standard InChIKey: LOCDPORVFVOGCR-UHFFFAOYSA-N
CAS Registry Number: 1618-26-4
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Other names: CH3SCH2SCH3; Bis(methylthio)methane; Formaldehyde dimethyl mercaptal; Methane, bis(methylthio)-; Bis(methylmercapto)methane; Methylenebis(methyl sulfide); Thioformaldehyde dimethylthioacetal; Bis(methylsulfanyl)methane; 2,4-Dithiopentane; NSC 96010; Thioformaldehyde dimethyl acetal; bis(methylthio)methan
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Other data available:
- Phase change data
- Mass spectrum (electron ionization)
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Gas phase ion energetics data

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Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.67	PE	Guimon, Guimon, et al., 1975	Vertical value; LLK
8.65	PE	Bock, Wagner, et al., 1972	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₂H₅S⁺	10.1 ± 0.15	SCH₃	EI	Broer, Weringa, et al., 1979	LLK

Gas Chromatography

Go To: Top, Gas phase ion energetics data, References, Notes

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	Apiezon M	130.	903.	Garbuzov, Misharina, et al., 1985	He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5	892.	Mahattanatawee K., Perez-Cacho P.R., et al., 2007	30. m/0.32 mm/0.5 μm, He, 7. K/min, 265. C @ 5. min; T_start: 40. C
Capillary	CP Sil 8 CB	880.	Mahadevan and Farmer, 2006	60. C @ 5. min, 4. K/min, 220. C @ 30. min; Column length: 50. m; Column diameter: 0.32 mm

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	SE-54	885.	Kubícková and Grosch, 1997	Column length: 30. m; Column diameter: 0.32 mm; Program: 35C (2min) => 40C/min => 50C (2min) => 4C/min => 250C (10min)
Capillary	SE-54	889.	Kubícková and Grosch, 1997	Column length: 30. m; Column diameter: 0.32 mm; Program: 35C (2min) => 40C/min => 50C (2min) => 4C/min => 250C (10min)

Van Den Dool and Kratz RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1290.	Mahattanatawee K., Perez-Cacho P.R., et al., 2007	30. m/0.32 mm/0.5 μm, He, 7. K/min, 240. C @ 5. min; T_start: 40. C
Capillary	CP-Wax 52CB	1272.	Mahadevan and Farmer, 2006	60. C @ 5. min, 4. K/min, 220. C @ 30. min; Column length: 50. m; Column diameter: 0.32 mm
Capillary	CP-Wax 52CB	1285.	Mahadevan and Farmer, 2006	60. C @ 5. min, 4. K/min, 220. C @ 30. min; Column length: 50. m; Column diameter: 0.32 mm
Capillary	DB-Wax	1282.	Shimoda, Peralta, et al., 1996	60. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 50. C; T_end: 230. C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	SPB-1	871.	Frerot, Velluz, et al., 2008	30. m/0.25 mm/1.0 μm, Helium, 60. C @ 5. min, 5. K/min; T_end: 250. C
Capillary	SPB-5	894.	Vasta, Ratel, et al., 2007	60. m/0.32 mm/1. μm, 40. C @ 5. min, 3. K/min, 230. C @ 5. min
Capillary	HP-1	862.	Bendimerad and Bendiab, 2005	50. m/0.2 mm/0.5 μm, He, 2. K/min, 250. C @ 60. min; T_start: 60. C
Capillary	DB-5	881.	Schlüter, Steinhart, et al., 1999	34. C @ 3. min, 5. K/min, 200. C @ 10. min; Phase thickness: 0.25 μm
Capillary	HP-5	889.	Kubec, Drhová, et al., 1998	30. m/0.25 mm/0.25 μm, N2, 40. C @ 3. min, 4. K/min, 240. C @ 10. min
Capillary	DB-1	873.	Rapior, Breheret, et al., 1997	30. m/0.2 mm/0.25 μm, He, 50. C @ 2. min, 4. K/min; T_end: 200. C
Capillary	SE-54	904.	Bellesia, Pinetti, et al., 1996	25. m/0.2 mm/0.5 μm, He, 35. C @ 2. min, 5. K/min; T_end: 250. C

Normal alkane RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	SPB-5	892.	Begnaud, Pérès, et al., 2003	60. m/0.32 mm/1. μm; Program: not specified
Capillary	Polydimethyl siloxane	894.	Spanier, Shahidi, et al., 2001	Program: not specified

Normal alkane RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	Innowax	1300.	Bendimerad and Bendiab, 2005	50. m/0.2 mm/0.5 μm, He, 2. K/min, 250. C @ 60. min; T_start: 60. C
Capillary	DB-Wax	1260.	Schlüter, Steinhart, et al., 1999	60. m/0.32 mm/0.25 μm, He, 34. C @ 3. min, 5. K/min, 200. C @ 10. min
Capillary	HP-Innowax	1289.	Kubec, Drhová, et al., 1998	30. m/0.25 mm/0.25 μm, N2, 40. C @ 3. min, 4. K/min, 190. C @ 10. min

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	EC-1000	1305.	Delabre and Bendall, 9999	Program: not specified
Capillary	CP Wax 52 CB	1274.	Patterson and Stevenson, 1995	50. m/0.32 mm/0.20 μm; Program: 50 0C (10 min) 2 0C/min -> 100 0C 5 0C/min -> 150 0C 7 0C/min -> 220 0C (20 min)
Capillary	Superox 0.6; Carbowax 20M	1256.	Waggott and Davies, 1984	Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
Capillary	Carbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc.	1256.	Waggott and Davies, 1984	Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

References

Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes

Guimon, Guimon, et al., 1975
Guimon, C.; Guimon, M.-F.; Pfister-Guillouzo, G., Application of photoelectron spectroscopy to conformational analysis of two 1,3-dithia compounds, Tetrahedron Lett., 1975, 17, 1413. [all data]

Bock, Wagner, et al., 1972
Bock, H.; Wagner, G.; Kroner, J., Photoelektronenspektren und molekuleigenschaften, XIV. Die delokalisation des schwefel-elektronenpaar in CH₃S-substituierten aromaten, Chem. Ber., 1972, 105, 3850. [all data]

Broer, Weringa, et al., 1979
Broer, W.J.; Weringa, W.D.; Nieuwpoort, W.C., Rearrangements and fragmentations of [C₂H₅S]⁺ ions, Org. Mass Spectrom., 1979, 14, 543. [all data]

Garbuzov, Misharina, et al., 1985
Garbuzov, V.G.; Misharina, T.A.; Aerov, A.F.; Golovnya, R.V., Gas chromatographic retention indices for sulphur(II)-containing organic substances, J. Anal. Chem. USSR (Engl. Transl.), 1985, 40, 4, 576-586. [all data]

Mahattanatawee K., Perez-Cacho P.R., et al., 2007
Mahattanatawee K.; Perez-Cacho P.R.; Davenport T.; Rouseff R., Comparison of three lychee cultivar odor profiles using gas chromatography-olfactometry and gas chromatography-sulfur detection, J. Agric. Food Chem., 2007, 55, 5, 1939-1944, https://doi.org/10.1021/jf062925p . [all data]

Mahadevan and Farmer, 2006
Mahadevan, K.; Farmer, L., Key Odor Impact Compounds in Three Yeast Extract Pastes, J. Agric. Food Chem., 2006, 54, 19, 7242-7250, https://doi.org/10.1021/jf061102x . [all data]

Kubícková and Grosch, 1997
Kubícková, J.; Grosch, W., Evaluation of potent odorants of camembert cheese by dilution and concentration techniques, Int. Dairy J., 1997, 7, 1, 65-70, https://doi.org/10.1016/S0958-6946(96)00044-1 . [all data]

Shimoda, Peralta, et al., 1996
Shimoda, M.; Peralta, R.R.; Osajima, Y., Headspace gas analysis of fish sauce, J. Agric. Food Chem., 1996, 44, 11, 3601-3605, https://doi.org/10.1021/jf960345u . [all data]

Frerot, Velluz, et al., 2008
Frerot, E.; Velluz, A.; Bagnoud, A.; Delort, E., Analysis of the volatile constituents of cooked petai beans (Parkia speciosa) using high-resolution GC/TOF-MS, Flav. Fragr. J., 2008, 23, 6, 434-440, https://doi.org/10.1002/ffj.1902 . [all data]

Vasta, Ratel, et al., 2007
Vasta, V.; Ratel, J.; Engel, E., Mass Spectrometry Analysis of Volatile Compounds in Raw Meat for the Authentication of the Feeding Background of Farm Animals, J. Agric. Food Chem., 2007, 55, 12, 4630-4639, https://doi.org/10.1021/jf063432n . [all data]

Bendimerad and Bendiab, 2005
Bendimerad, N.; Bendiab, S.A.T., Composition and antibacterial activity of Pseudocytisus integrifolius (Salisb.) essential oil from Algeria, J. Agric. Food Chem., 2005, 53, 8, 2947-2952, https://doi.org/10.1021/jf047937u . [all data]

Schlüter, Steinhart, et al., 1999
Schlüter, S.; Steinhart, H.; Schwarz, F.J.; Kirchgessner, M., Changes in the odorants of boiled carp fillet (Cyprinus carpio L.) as affected by increasing methionine levels in feed, J. Agric. Food Chem., 1999, 47, 12, 5146-5150, https://doi.org/10.1021/jf9902604 . [all data]

Kubec, Drhová, et al., 1998
Kubec, R.; Drhová, V.; Velísek, J., Thermal degradation of S-methylcysteine and its sulfoxide-important flavor precursors of Bassica and Allium vegetables, J. Agric. Food Chem., 1998, 46, 10, 4334-4340, https://doi.org/10.1021/jf980379x . [all data]

Rapior, Breheret, et al., 1997
Rapior, S.; Breheret, S.; Talou, T.; Bessiére, J.-M., Volatile flavor constituents of fresh Marasmius alliaceus (garlic Marasmius), J. Agric. Food Chem., 1997, 45, 3, 820-825, https://doi.org/10.1021/jf960511y . [all data]

Bellesia, Pinetti, et al., 1996
Bellesia, F.; Pinetti, A.; Bianchi, A.; Tirillini, B., Volatile compounds of the white truffle (Tuber magnaturn Pico) from middle Italy, Flavour Fragr. J., 1996, 11, 4, 239-243, https://doi.org/10.1002/(SICI)1099-1026(199607)11:4<239::AID-FFJ573>3.0.CO;2-A . [all data]

Begnaud, Pérès, et al., 2003
Begnaud, F.; Pérès, C.; Berdagué, J.-L., Characterization of volatile effluents of livestock buildings by solid-phase microextraction, Int. J. Environ. Anal. Chem., 2003, 83, 10, 837-849, https://doi.org/10.1080/03067310310001603349 . [all data]

Spanier, Shahidi, et al., 2001
Spanier, A.M.; Shahidi, F.; Par; iment, T.H.; Mussinan, C., Food Flavors and Chemistry. Advances of the New Millenium, Royal Soc. Chem., 2001, 666. [all data]

Delabre and Bendall, 9999
Delabre, M.-L.; Bendall, J.F., Flavour ingredients from fermented dairy streams, Expression of Multidisciplinary Flavour Sci., 9999, 375-378. [all data]

Patterson and Stevenson, 1995
Patterson, R.L.S.; Stevenson, M.H., Irradiation-induced off-odor in chicken and its possible control, British Poultry Science, 1995, 36, 3, 425-441, https://doi.org/10.1080/00071669508417789 . [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Notes

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Symbols used in this document:

AE Appearance energy
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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