2,2'-Dipyridyldisulfide: Difference between revisions

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Revision as of 12:12, 10 February 2011 editBeetstra (talk \| contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit		Revision as of 12:18, 19 April 2011 edit undoCheMoBot (talk \| contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (Next edit →
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	{{orphan\|date=December 2008}}		{{orphan\|date=December 2008}}
	{{chembox		{{chembox
			\| verifiedrevid = 413095043
	\| Name = 2,2'-Dipyridyldisulfide		\| Name = 2,2'-Dipyridyldisulfide
	\| ImageFile = 2,2'-Dipyridyldisulfide.svg		\| ImageFile = 2,2'-Dipyridyldisulfide.svg
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	\| OtherNames = 2,2'-Dipyridyldisulphide<br />Aldrithiol-2		\| OtherNames = 2,2'-Dipyridyldisulphide<br />Aldrithiol-2
	\| Section1 = {{Chembox Identifiers		\| Section1 = {{Chembox Identifiers
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 58603		\| ChemSpiderID = 58603
	\| InChI = 1/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H		\| InChI = 1/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H
	\| InChIKey = HAXFWIACAGNFHA-UHFFFAOYAJ		\| InChIKey = HAXFWIACAGNFHA-UHFFFAOYAJ
	\| SMILES1 = c1ccnc(c1)SSc2ccccn2		\| SMILES1 = c1ccnc(c1)SSc2ccccn2
			\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ChEMBL = 118678		\| ChEMBL = 118678
			\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 1S/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H		\| StdInChI = 1S/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H
			\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = HAXFWIACAGNFHA-UHFFFAOYSA-N		\| StdInChIKey = HAXFWIACAGNFHA-UHFFFAOYSA-N
	\| CASNo = 2127-03-9		\| CASNo = 2127-03-9

Revision as of 12:18, 19 April 2011

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2,2'-Dipyridyldisulfide
Names

IUPAC name 2,2'-Dipyridyldisulfide
Other names 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
CompTox Dashboard (EPA)	DTXSID70175517
InChI InChI=1S/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8HKey: HAXFWIACAGNFHA-UHFFFAOYSA-N InChI=1/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8HKey: HAXFWIACAGNFHA-UHFFFAOYAJ
SMILES S(Sc1ncccc1)c2ncccc2 c1ccnc(c1)SSc2ccccn2
Properties
Chemical formula	C₁₀H₈N₂S₂
Molar mass	220.31 g·mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Irritant (Xi)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

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

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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