1,3-Propanedithiol

1,3-Propanedithiol
IUPAC name

Propane-1,3-dithiol
Other names

1,3-dimercaptopropane
Identifiers
CAS number 109-80-8 Y
ChemSpider 13848090 Y
ChEBI CHEBI:44864 Y
ChEMBL CHEMBL1235209 N
RTECS number TZ2585500
Jmol-3D images Image 1
Properties
Molecular formula C3H8S2
Molar mass 108.23 g mol−1
Appearance Colorless liquid
Density 1.078 g/cm³
Melting point

-79 °C, 194 K, -110 °F
Boiling point

169 °C, 442 K, 336 °F
Solubility in water slight
Solubility in solvents all organic solvents
Refractive index (nD) 1.539
Structure
Dipole moment 0 D
Hazards
R-phrases R36/37/38
S-phrases S26
Main hazards stench
Flash point 138 °F
Related compounds
Related compounds 1,2-ethanedithiol
1,2-propanedithiol
lipoic acid
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

Contents

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 diiron derivative:[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:10.1002/047084289. 
  2. ^ Corey, E. J.; Seebach, D. (1988), "1,3-Dithiane", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0556 ; Coll. Vol. 6: 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.