2,2'-Dipyridyldisulfide

2,2'-Dipyridyldisulfide
Skeletal formula of DPS
Space-filling model of the DPS molecule
Names
Preferred IUPAC name
2,2'-Disulfanediyldipyridine
Other names
1,2-Di(pyridin-2-yl)disulfane (not recommended)
2,2'-Dipyridyldisulfide
2,2'-Dipyridyldisulphide
Aldrithiol-2
Identifiers
2127-03-9
3D model (Jmol) Interactive image
Interactive image
ChEMBL ChEMBL118678 YesY
ChemSpider 58603 YesY
ECHA InfoCard 100.016.676
UNII L6X912UPBU YesY
Properties
C10H8N2S2
Molar mass 220.31 g·mol−1
Melting point 56 to 58 °C (133 to 136 °F; 329 to 331 K)
Hazards
Main hazards Irritant (Xi)
R-phrases R36/37/38
S-phrases S36/37/39
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

2,2'-Dipyridyldisulfide, sometimes known as DPS, is used for preparing thiols[1][2] and activating or protecting carboxylic acid with triphenylphosphine in the following reaction.[3]

Uses

It is also used in molecular biology as an oxidising agent, for example to oxidise free thiols to form disulfide bonds in proteins.

References

  1. Futaki S. and Kitagawa K. (1994). "Peptide-Unit Assembling Using Disulfide Cross-Linking - a New Approach for Construction of Protein Models". Tetrahedron Lett. 35 (8): 1267–1270. doi:10.1016/0040-4039(94)88040-9.
  2. "Special Reagents for Thiol Groups". Aldrichimica Acta. 4 (3): 33–46.
  3. Thalmann A., Oertle K. and Gerlach H. "Synthesis of ricinelaidic acid lactone". Org. Synth. 7: 470.


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