1,3-Propanedithiol

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1,3-Propanedithiol
1,3-Propanedithiol
1,3-Propanedithiol molecule
Names
IUPAC name
Propane-1,3-dithiol
Other names
1,3-dimercaptopropane
Identifiers
109-80-8 YesY
ChEBI CHEBI:44864 YesY
ChEMBL ChEMBL1235209 N
ChemSpider 13848090 YesY
Jmol 3D model Interactive image
RTECS number TZ2585500
  • InChI=1S/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2 YesY
    Key: ZJLMKPKYJBQJNH-UHFFFAOYSA-N YesY
  • 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
Vapor pressure {{{value}}}
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 YesYN ?)
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.

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 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

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

See also

References

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