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2,2'-Dipyridyl Disulfide [for Peptide Synthesis]
(CAS RN:2127-03-9 Product Number:D1114)

Structure

2,2'-Dipyridyl Disulfide
Synonym 2,2'-Dithiodipyridine

General Information

Product Number D1114

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Purity/Analysis Method >98.0%(GC)(T)
Storage Temperature
M.F. / M.W. C10H8N2S2=220.31
CAS RN 2127-03-9
Related CAS RN
MDL Number MFCD00006287
Packaging and Container
  • Product Details
  • Safety & Regulations

Specification

Purity(GC) min. 98.0 %
Purity(Nonaqueous Titration) min. 98.0 %
Melting point 57.0 to 60.0 deg-C
Solubility in Methanol almost transparency

References

Beilstein 21,45
Reaxys-RN 154629
PubChem SID 87567675
F&F 6,246
EC Number 218-343-1

GHS

Pictogram
Signal Word Warning
Hazard Statements
  • H315
  • :Causes skin irritation.
  • H319
  • :Causes serious eye irritation.
Precautionary Statements
  • P264
  • :Wash hands and face thoroughly after handling.
  • P280
  • :Wear protective gloves, eye protection.
  • P302+P352+P332+P313+P362+P364
  • :IF ON SKIN: Wash with plenty of water. If skin irritation occurs: Get medical advice or attention. Take off contaminated clothing and wash it before reuse.
  • P305+P351+P338+P337+P313
  • :IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice or attention.

Transport Information

HS Number 2933399990

Application

Corey-Nicolaou Macrolactonization1)

Typical Procedure:
To a stirred solution of the hydroxy carboxylic acid 1 (125 mg, 0.422 mmol) in dry CH2Cl2 (15 mL) is added triphenylphosphine (125 mg, 0.48 mmol) followed by 2,2’-dipyridyl disulfide (105 mg, 0.48 mmol) and the mixture is stirred until TLC (ethyl acetate : hexane = 2 : 3) shows complete loss of starting material (usually 0.5 h – 2 h). The mixture is concentrated in vacuo and dissolved in dry toluene (150 mL). To the solution is added 0.006M AgBF4 solution in toluene (1.2 mL) and the mixture is heated under reflux for 12 h. The mixture is cooled and solvents removed in vacuo. The residue is purified by flash column chromatography (acetone : CH2Cl2 = 0.5 : 99.5) to afford the desired lactone 2 (95 mg, Y. 81%).

References

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