1,3-Propanedithiol

Chembox new
Name = 1,3-Propanedithiol
ImageFile = H2pdt.png ImageSize = 100px
ImageName = 1,3-Propanedithiol
IUPACName = 1,3-Propanedithiol
OtherNames = 1,3-dimercaptopropane
Section1 = Chembox Identifiers
SMILES =
CASNo = 109-80-8
RTECS = TZ2585500
Section2 = Chembox Properties
Formula = C₃H₈S
MolarMass = 108.23 g/mol
Appearance = colourless liquid, stench
Density = 1.078 g/cm³
Solubility = slight
Solvent = solvents
SolubleOther = all organic solvents
MeltingPt = -79 °C
BoilingPt = 169 °C
pKb =
RefractIndex = 1.539
Section3 = Chembox Structure
Dipole = 0 D
Section7 = Chembox Hazards
MainHazards = stench
FlashPt = 138 °F
RPhrases = 36/37/38
SPhrases = 26
Section8 = Chembox Related
OtherCpds = 1,2-ethanedithiol
1,2-propanedithiol
lipoic acid

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. [cite encyclopedia
author = Conrow, R. E.; Le Huérou, Y.
title = 1,3-Propanedithiol
Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette)
date = 2004
publisher = J. Wiley & Sons, New York
doi = 10.1002/047084289] A prototypical reaction is its formation of 1,3-dithiane from from formaldehyde. [OrgSynth
author = Corey, E. J.; Seebach, D.
title = 1,3-Dithiane
year = 1988
collvol = 6
collvolpages = 556
prep = cv6p0556] 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. [cite journal
author = Liu, Q.; Che, G. Yu, H.; Liu, Y.; Zhang, J. Zhang, Q.; Dong, D.
title = The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization
journal = Journal of Organic Chemistry
year = 2003
volume = 68
pages = 9148–9150
doi = 10.1021/jo034702t]

Use in inorganic synthesis

1,3-Propanedithiol reacts with metal ions to form chelate rings. Illustrative is the synthesis of the diiron derivative: [cite journal
author = Winter, A.; Zsolnai, L. and Huttner, G.
title = Zweikernige und dreikernige Carbonyleisenkomplexe mit 1,2- und 1,3-Dithiolatobrückenliganden
journal = Zeitschrift für Naturforschung
year = 1982
volume = 37b
pages = 1430–1436
doi = ] :Fe₃(CO)₁₂ + C₃H₆(SH)₂ → Fe₂(S₂C₃H₆)(CO)₆ + H₂ + Fe(CO)₅ + CO

afety

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

ee also

*1,2-Propanedithiol

References