Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references
1,3-Propanedithiol is the chemical compound with the formula HSCH2CH2CH2SH. This dithiol is a useful reagent in organic synthesis. This liquid, which is readily available commercially, has an intense stench.
1,3-Propanedithiol is mainly used for the protection of aldehydes and ketones via their reversible formation of dithianes.[1] A prototypical reaction is its formation of 1,3-dithiane from from formaldehyde.[2] The reactivity of this dithiane illustrates the concept of umpolung.
The unpleasant odour of 1,3-propanedithiol has encouraged the development of alternative reagents that generate similar derivatives.[3]
Use in inorganic synthesis
1,3-Propanedithiol reacts with metal ions to form chelate rings. Illustrative is the synthesis of the diiron derivative:[4]
The stench of 1,3-propanedithiol can be neutralized with bleach.
See also
1,2-Propanedithiol
References
^ Conrow, R. E.; Le Huérou, Y. (2004). "1,3-Propanedithiol".. J. Wiley & Sons, New York. DOI:10.1002/047084289.
^ Corey, E. J.; Seebach, D. (1988). "1,3-Dithiane". Org. Synth.; Coll. Vol.6: 556.
^ Liu, Q.; Che, G. Yu, H.; Liu, Y.; Zhang, J. Zhang, Q.; Dong, D. (2003). "The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization". Journal of Organic Chemistry68: 9148 - 9150. doi:10.1021/jo034702t.
^ Winter, A.; Zsolnai, L. and Huttner, G. (1982). "Zweikernige und dreikernige Carbonyleisenkomplexe mit 1,2- und 1,3-Dithiolatobrückenliganden". Zeitschrift für Naturforschung37b: 1430-1436.
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