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Pyridinium chlorochromate

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Pyridinium chlorochromate Basic information
Pyridinium chlorochromate Chemical Properties
  • Melting point:205-208 °C(lit.)
  • storage temp. Inert atmosphere,Room Temperature
  • solubility Soluble in acetone, benzene, dichloromethane, acetonitrile and tetrahydrofuran.
  • form Crystalline Powder
  • color Orange
  • Sensitive Moisture Sensitive
  • Merck 14,7974
  • BRN 7054643
  • Stability:Stable. May react with easily oxidized materials. Incompatible with reducing agents, combustible material, metals, strong reducing agents.
  • InChIKeyLEHBURLTIWGHEM-UHFFFAOYSA-N
  • CAS DataBase Reference26299-14-9(CAS DataBase Reference)
  • EPA Substance Registry SystemPyridinium chlorochromate (26299-14-9)
Safety Information
MSDS
Pyridinium chlorochromate Usage And Synthesis
  • Chemical PropertiesPyridinium chlorochromate is orange crystalline powder
  • UsesPyridinium chlorochromate is usually used to oxidize an allylic methylene group.
    Oxidation of primary alcohols to aldehydes
    Oxidation of primary alcohols to aldehydes
    Pyridinium dichromate (PDC) or pyridinium chlorochromate (PCC) in anhydrous media such as dichloromethane oxidizes primary alcohols to aldehydes while avoiding overoxidation to carboxylic acids.
  • UsesOxidizing agent in organic synthesis.
    PCC is pyridinium chlorochromate; PDC is pyridinium dichromate. Both are used in dichloromethane.
  • ReactionsPyridinium chlorochromate (PCC) is a widespread used oxidation reagent but lacks of selectivity with unsaturated compounds. Furthermore, the workup procedure is quite tedious. Absorption of PCC onto silica gel improves the oxidation but then a reagent excess is necessary to reach appropriate rates. These drawbacks can be overcome by sonication leading to short reaction times and only an small excess of 1.2.-1.5 eq. of PCC is required. Using this reagent has been used to oxidise borneol to camphor in 85% yield.
    Pyridinium chlorochromate Reaction
  • Purification MethodsDry it in a vacuum for 1hour. It is not hygroscopic and can be stored for extended periods at room temperature without change. If the purity is very suspect, it can be readily prepared. [Corey & Scuggs Tetrahedron Lett 2647 1975, Piancatelli et al. Synthesis 245 1982.] (Possible CARCINOGEN.) § Available commercially on a polymer support.
Pyridinium chlorochromate Preparation Products And Raw materials
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