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;
ChEBI	CHEBI:143170;
ChEMBL	ChEMBL118678 ;
ChemSpider	58603 ;
ECHA InfoCard	100.016.676
EC Number	218-343-1;
PubChem CID	65093;
UNII	L6X912UPBU ;
CompTox Dashboard (EPA)	DTXSID70175517 ;
	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)
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
	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 carboxylic acid for coupling reactions, as 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. "Ricinelaidic acid lactone". Org. Synth. 7: 470. doi:10.15227/orgsyn.063.0192.

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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. "Ricinelaidic acid lactone". Org. Synth. 7: 470. doi:10.15227/orgsyn.063.0192.