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2,2'-Dipyridyl disulfide, 98%, Thermo Scientific Chemicals
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Catalog number A11118.22
also known as A11118-22
Price (USD)/ Each
747.00
-
Quantity:
100 g
Price (USD)/ Each
747.00
2,2'-Dipyridyl disulfide, 98%, Thermo Scientific Chemicals
Catalog numberA11118.22
Price (USD)/ Each
747.00
-
Chemical Identifiers
CAS2127-03-9
IUPAC Name2-(pyridin-2-yldisulfanyl)pyridine
Molecular FormulaC10H8N2S2
InChI KeyHAXFWIACAGNFHA-UHFFFAOYSA-N
SMILESS(SC1=CC=CC=N1)C1=CC=CC=N1
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Specifications
Specification Sheet
Specification SheetCommentSpecification differs for U.S. and non-U.S. material where indicated
Identification (FTIR)Conforms (non-U.S. specification)
Melting Point (clear melt)55-60°C
Appearance (Color)White to cream to yellow to pale brown
FormPowder or crystalline powder
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2,2'-Dipyridyl disulfide is a useful reagent for determination of sulfhydryl groups, preparation of amino acid active esters and the thio esters of phosphoric acid. It acts as a peptide coupling reagent and as an oxidizing agent. It is also used for the activation of glycosides.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
2,2′-Dipyridyl disulfide is a useful reagent for determination of sulfhydryl groups, preparation of amino acid active esters and the thio esters of phosphoric acid. It acts as a peptide coupling reagent and as an oxidizing agent. It is also used for the activation of glycosides.
Solubility
Soluble in water, benzene, tetrahydrofuran, dichloromethane, acetonitrile and dimethyformamide.
Notes
Incompatible with oxidizing agents and metals.
2,2′-Dipyridyl disulfide is a useful reagent for determination of sulfhydryl groups, preparation of amino acid active esters and the thio esters of phosphoric acid. It acts as a peptide coupling reagent and as an oxidizing agent. It is also used for the activation of glycosides.
Solubility
Soluble in water, benzene, tetrahydrofuran, dichloromethane, acetonitrile and dimethyformamide.
Notes
Incompatible with oxidizing agents and metals.
RUO – Research Use Only
General References:
- In combination with triphenylphosphine, acts as a peptide coupling reagent (see Appendix 6) in which water is removed by a mechanism whereby the phosphine is oxidized to the phosphine oxide and the disulfide reduced to the thiol: J. Am. Chem. Soc., 90, 4490 (1968); 91, 1554 (1969); Bull. Chem. Soc. Jpn., 43, 1271 (1970).
- The technique has also been widely applied for macrolactonization, via high-dilution cyclization of the 2-pyridine thioester: J. Am. Chem. Soc., 96, 5614 (1974); 97, 653, 654, 2287 (1975). The cyclization step can be catalyzed by silver ion: Helv. Chim. Acta, 57, 2661 (1974). See, e.g.: Org. Synth. Coll., 7, 470 (1990).
- In combination with tri-n-butylphosphine has been used for the activation of glycosides, e.g. in the formation of disaccarides: J. Am. Chem. Soc., 103, 4221 (1981); Tetrahedron, 47, 6435 (1991).
- Moosun, S.; Laulloo, S. J.; Bhowon, M. G. Metal complexes of diaryl and 2, 2'-dipyridyl disulfides. J. Sulphur Chem. 2012, 33 (6), 661-691.
- Bhasin, K. K.; Kumar, R.; Mehta, S. K.; Raghavaiah, P.; Jacob, C.; Klapotke, T. M. Synthesis and characterization of 5, 5'-dibromo-2, 2'-dipyridyl disulfide and some of its derivatives: X-ray structure of 5, 5'-dibromo-2, 2'-dipyridyl disulfide and bis (5-bromopyridine-2-ylthio) methane. Inorg. Chim. Acta 2009, 362 (7), 2386-2390.