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2,2'-Dipyridyldisulfide

From Wikipedia, the free encyclopedia

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.016.676 Edit this at Wikidata
EC Number
  • 218-343-1
UNII
  • InChI=1S/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H checkY
    Key: HAXFWIACAGNFHA-UHFFFAOYSA-N checkY
  • InChI=1/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H
    Key: HAXFWIACAGNFHA-UHFFFAOYAJ
  • S(Sc1ncccc1)c2ncccc2
  • c1ccnc(c1)SSc2ccccn2
Properties
C10H8N2S2
Molar mass 220.31 g·mol−1
Melting point 56 to 58 °C (133 to 136 °F; 329 to 331 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant (Xi)
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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

  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 (1985). "Ricinelaidic acid lactone". Org. Synth. 7: 470. doi:10.15227/orgsyn.063.0192.


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This page was last edited on 15 May 2024, at 15:32
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