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 (Jmol)	Interactive image
ChEBI	CHEBI:44864 Y
ChemSpider	13848090 Y
ECHA InfoCard	100.003.371
RTECS number	TZ2585500
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
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
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).
N  (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.

1,3-Propanedithiol is mainly used for the protection of aldehydes and ketones via their reversible formation of dithianes. A prototypical reaction is its formation of 1,3-dithiane from formaldehyde. 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.

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

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:

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