2,2'-Dipyridyldisulfide

2,2'-Dipyridyldisulfide
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
CAS Number	2127-03-9;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL118678 ;
ChemSpider	58603 ;
ECHA InfoCard	100.016.676
UNII	L6X912UPBU ;
	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R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S36/37/39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

↑ 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.
↑ "Special Reagents for Thiol Groups". Aldrichimica Acta. 4 (3): 33–46.
↑ Thalmann A., Oertle K. and Gerlach H. "Synthesis of ricinelaidic acid lactone". Org. Synth. 7: 470.

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[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.