Pyridinium chlorochromate

• Catalog No.: A11752
• CAS Number: 26299-14-9
• M. F.: C5H6ClCrNO3
• M. W.: 215.55514
• Purity: 98%

SYNONYMS

• Title: 氯铬酸吡啶鎓
• IUPAC name: pyridin-1-ium chlorochromiumoylolate
• IUPAC Traditional name: pyridium chlorochromiumoylolate
• Synonyms: PCC

DATABASE IDS

• CAS Number: 26299-14-9
• MDL Number: MFCD00013106
• EC Number: 247-595-5
• Merck Index: 147974

PROPERTIES

• Purity: 98%
• Melting Point: ca 206°C dec.
• GHS Hazard statements: H350-H272-H400-H410-H317
• European Hazard Symbols: Toxic (T)
• European Hazard Symbols: Oxidising (O)
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P221-P210-P302+P352-P321-P405-P501A
• Risk Statements: 49-8-43-50/53
• Safety Statements: 53-45-60-61
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 5.1
• UN Number: UN1479
• Packing Group: II

REFERENCES

• Mild, selective oxidant for alcohols to aldehydes or ketones: Tetrahedron Lett., 2647 (1975); review: Synthesis, 245 (1982). Superior results have been reported with a catalytic amount of acetic acid: Tetrahedron, 46, 4417 (1990). Adsorption of the reagent onto alumina simplifies work-up and enhances reactivity in hydrocarbon solvents: Synthesis, 223 (1980). Improved results have also been obtained in the presence of silica gel, where reaction times are shortened by sonication: J. Org. Chem., 54, 5387 (1989). Oxidation of methylarenes to benzaldehydes has been reported. Selective mono-oxidation of xylenes to tolualdehydes can be achieved: Synlett, 2769 (2005).
• For 18-crown-6 complexes of chlorochromates as mild, selective oxidants, see: J. Org. Chem., 60, 2267 (1995). See also 1H-Pyrazole, A14186.
• Trialkyl boranes are also oxidized to carbonyl compounds, non-terminal boranes giving ketones: J. Organomet. Chem., 162, C9 (1978) and terminal boranes giving aldehydes: J. Organomet. Chem., 172, C20 (1979). Similarly, aldehydes can be prepared from terminal alkenes by oxidation of their adducts with thexylborane: Synthesis, 151 (1980).
• In THF, arylhydroxylamines are selectively oxidized to nitroso compounds: Synth. Commun., 22, 1683 (1992).
• For a brief feature on novel oxidation reactions with this reagent, see: Synlett, 741 (2003).