I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
Pyridinium chlorochromate is used as an oxidizing agent to convert primary and secondary alcohols to aldehydes and ketones respectively. It is involved in the preparation of cyclohexanone, (-)-pulegone and lactones. It plays an important role in the selective mono-oxidation of xylenes to tolualdehydes and arylhydroxyamines to nitroso compounds. Furthermore, it is utilized as an oxidant for amino acids, L-cystine, aniline, cycloalkanols, vicinal and non-vicinal diols as well as in the Babler oxidation reaction.
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).
Luong, S.; Ung, A. T.; Kalman, J.; Fu, S. Transformation of codeine and codeine-6-glucuronide to opioid analogues by urine adulteration with pyridinium chlorochromate: potential issue for urine drug testing. Rapid Commun. Mass Spectrom. 2014, 28 (14), 1609-1620.
Luong, S.; Kuzhiumparambil, U.; Fu, S. Elucidation of markers for monitoring morphine and its analogs in urine adulterated with pyridinium chlorochromate. Bioanalysis 2015, 7 (18), 2283-2295.
Gefahrenhinweise (EU): H272-H317-H350
May intensify fire; oxidizer. May cause an allergic skin reaction. May cause cancer.
Take any precaution to avoid mixing with combustibles. Obtain special instructions before use. Keep/Store away from clothing/combustible materials. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.