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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.
Hazard Statements: H272-H317-H350i
May intensify fire; oxidizer. May cause an allergic skin reaction. May cause cancer by inhalation.
Precautionary Statements: P201-P202-P210-P220-P221-P261-P272-P280g-P281-P302+P352-P308+P313-P333+P313-P363-P370+P378q-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep/Store away from clothing/combustible materials. Take any precaution to avoid mixing with combustibles. Avoid breathing dust/fume/gas/mist/vapours/spray. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves. Use personal protective equipment as required. IF ON SKIN: Wash with plenty of soap and water. IF exposed or concerned: Get medical advice/attention. If skin irritation or rash occurs: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant