Propane-1,3-dithiol

1,3-Propanedithiol

1,3-Propanedithiol
Names
Preferred IUPAC name Propane-1,3-dithiol
Other names 1,3-Dimercaptopropane
Identifiers
CAS Number	109-80-8  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:44864  Y
ChEMBL	ChEMBL1235209  N
ChemSpider	13848090  Y
ECHA InfoCard	100.003.371
EC Number	203-706-9
PubChem CID	8013
RTECS number	TZ2585500
UNII	R4LUJ82U52
UN number	3336
CompTox Dashboard (EPA)	DTXSID0059376
InChI InChI=1S/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2 Y Key: ZJLMKPKYJBQJNH-UHFFFAOYSA-N Y 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
Odor	Offensive
Density	1.078 g/cm3
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
Occupational safety and health (OHS/OSH):
Main hazards	stench
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335
Precautionary statements	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, 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). N  verify  (what is  YN ?) 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.

Reactions

1,3-Propanedithiol has been 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]

Oxidation gives not the 1,2-dithiolane, but the bis(disulfide).

Structure of (C₃H₆S₂)₂, the oxidized "dimer" of 1,3-propanedithiol.

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

1,3-Propanedithiol reacts with metal ions to form dithiolates. Illustrative is the synthesis of the derivative diiron propanedithiolate hexacarbonyl upon reaction with triiron dodecacarbonyl: ^[5]

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

Safety

The stench of 1,3-propanedithiol can be minimized 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:10.1002/047084289X. hdl: 10261/236866 . ISBN   9780471936237.
2. Corey, E. J.; Seebach, D. (1988). "1,3-Dithiane". Organic Syntheses ; Collected Volumes, 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. Goodrow, Marvin H.; Olmstead, Marilyn M.; Musker, W. Kenneth (1983). "Preparation and X-Ray Crystal Structure of the Cyclic Dimer of 1,2-Dithiolane: 1,2,6,7-Tetrathiacyclodecane". Phosphorus and Sulfur and the Related Elements. 16 (3): 299–302. doi:10.1080/03086648308080483.
5. Hogarth, Graeme (2023). "An Unexpected leading role for [Fe₂(CO)₆(μ-PDT)] in our Understanding of [FeFe]-H₂ases and the Search for Clean Hydrogen Production". Coordination Chemistry Reviews. 490. doi:10.1016/j.ccr.2023.215174.