1,3-Propanedithiol

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
Names
Preferred IUPAC name
Propane-1,3-dithiol
Other names
1,3-Dimercaptopropane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.371
EC Number
  • 203-706-9
RTECS number
  • TZ2585500
UNII
UN number 3336
Properties
C3H8S2
Molar mass 108.22 g·mol−1
Appearance Colorless liquid
Density 1.078 g/cm3
Melting point −79 °C (−110 °F; 194 K)
Boiling point 169 °C (336 °F; 442 K)
slight
Solubility in solvents all organic solvents
1.539
Structure
0 D
Hazards
Main hazards stench
GHS pictograms
GHS Signal word Warning
H302, H315, H319, H335
P261, P264, P270, P271, P280, P301+312, P302+352, P304+340, P305+351+338, P312, P321, P330, P332+313, P337+313, P362, P403+233, P405, P501
Flash point 138 °C (280 °F; 411 K)
Related compounds
Related compounds
 1,2-ethanedithiol
1,2-propanedithiol
lipoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Use in organic synthesis

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 formaldehyde.[2] The reactivity of this dithiane illustrates the concept of umpolung. Alkylation gives thioethers, e.g. 1,5-dithiacyclooctane.

The unpleasant odour of 1,3-propanedithiol has encouraged the development of alternative reagents that generate similar derivatives.[3]

1,3-Propanedithiol is used in the synthesis of tiapamil.

Use in inorganic synthesis

1,3-Propanedithiol reacts with metal ions to form chelate rings. Illustrative is the synthesis of the derivative diiron propanedithiolate hexacarbonyl upon reaction with triiron dodecacarbonyl:[4]

Fe3(CO)12 + C3H6(SH)2 → Fe2(S2C3H6)(CO)6 + H2 + Fe(CO)5 + CO

Safety

The stench of 1,3-propanedithiol can be neutralized with bleach.

See also

References
  1. Conrow, R. E.; Le Huérou, Y. (2004). "1,3-Propanedithiol". Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette). J. Wiley & Sons, New York. doi:10.1002/047084289X.
  2. Corey, E. J.; Seebach, D. (1988). "1,3-Dithiane". Organic Syntheses.; Collective Volume, 6, p. 556
  3. 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 Chemistry. 68 (23): 9148–9150. doi:10.1021/jo034702t. PMID 14604400.
  4. Winter, A.; Zsolnai, L.; Huttner, G. (1982). "Zweikernige und dreikernige Carbonyleisenkomplexe mit 1,2- und 1,3-Dithiolatobrückenliganden". Zeitschrift für Naturforschung. 37b: 1430–1436.
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