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Propane-1,3-dithiol

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(Redirected from 1,3-Propanedithiol)
1,3-Propanedithiol
1,3-Propanedithiol
1,3-Propanedithiol molecule
Names
Preferred IUPAC name
Propane-1,3-dithiol
Other names
1,3-Dimercaptopropane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.371 Edit this at Wikidata
EC Number
  • 203-706-9
RTECS number
  • TZ2585500
UNII
UN number 3336
  • InChI=1S/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2 checkY
    Key: ZJLMKPKYJBQJNH-UHFFFAOYSA-N checkY
  • InChI=1/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2
    Key: ZJLMKPKYJBQJNH-UHFFFAOYAS
  • SCCCS
Properties
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)
slight
Solubility in solvents all organic solvents
1.539
Structure
0 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
stench
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H315, H319, H335
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 checkY☒N ?)

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

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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. 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]

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

Use in inorganic synthesis

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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

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

See also

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References

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  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. ^ Winter, A.; Zsolnai, L.; Huttner, G. (1982). "Zweikernige und dreikernige Carbonyleisenkomplexe mit 1,2- und 1,3-Dithiolatobrückenliganden". Zeitschrift für Naturforschung. 37b: 1430–1436. doi:10.1515/znb-1982-1113. S2CID 98749484.