2,2'-Dipyridyldisulfide

2,2'-Dipyridyldisulfide

Names
IUPAC name 2,2'-Dipyridyldisulfide
Other names 2,2'-Dipyridyldisulphide Aldrithiol-2
Identifiers
CAS Number	2127-03-9
ChEMBL	ChEMBL118678
ChemSpider	58603
Jmol interactive 3D	Image Image
InChI InChI=1S/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H Key: HAXFWIACAGNFHA-UHFFFAOYSA-N InChI=1/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H Key: HAXFWIACAGNFHA-UHFFFAOYAJ
SMILES S(Sc1ncccc1)c2ncccc2 c1ccnc(c1)SSc2ccccn2
Properties
Chemical formula	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.