2,2'-Dipyridyl disulfide

• Catalog No.: A11118
• CAS Number: 2127-03-9
• M. F.: C10H8N2S2
• M. W.: 220.31392
• Purity: 98%

SYNONYMS

• Title: 2,2'-二吡啶基 二硫醚
• IUPAC name: 2-(pyridin-2-yldisulfanyl)pyridine
• IUPAC Traditional name: 2,2'-dipyridyldisulfide
• Synonyms: 2,2'-Dithiodipyridine

DATABASE IDS

• CAS Number: 2127-03-9
• MDL Number: MFCD00006287
• EC Number: 218-343-1
• Beilstein Number: 154629

PROPERTIES

• Purity: 98%
• Flash Point: 210°C(410°F)
• Melting Point: 56-59°C
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否

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).