1,3-Propanedithiol

1,3-Propanedithiol

Names
IUPAC name Propane-1,3-dithiol
Other names 1,3-dimercaptopropane
Identifiers
CAS Number	109-80-8
ChEBI	CHEBI:44864
ChEMBL	ChEMBL1235209
ChemSpider	13848090
Jmol interactive 3D	Image
RTECS number	TZ2585500
InChI InChI=1S/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2 Key: ZJLMKPKYJBQJNH-UHFFFAOYSA-N InChI=1/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2 Key: ZJLMKPKYJBQJNH-UHFFFAOYAS
SMILES SCCCS
Properties
Chemical formula	C3H8S2
Molar mass	108.22 g·mol^−1
Appearance	Colorless liquid
Density	1.078 g/cm^3
Melting point	−79 °C (−110 °F; 194 K)
Boiling point	169 °C (336 °F; 442 K)
Solubility in water	slight
Solubility in solvents	all organic solvents
Refractive index (nD)	1.539
Structure
Dipole moment	0 D
Hazards
Main hazards	stench
R-phrases	R36/37/38
S-phrases	S26
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

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.

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.

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 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

• 1,2-Propanedithiol

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:10.1002/047084289.
2. Corey, E. J.; Seebach, D. (1988). "1,3-Dithiane". Org. Synth.; Coll. Vol. 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. and Huttner, G. (1982). "Zweikernige und dreikernige Carbonyleisenkomplexe mit 1,2- und 1,3-Dithiolatobrückenliganden". Zeitschrift für Naturforschung 37b: 1430–1436.