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26299-14-9 - Pyridinium chlorochromate, 98% - PCC - A11752 - Alfa Aesar

A11752 Pyridinium chlorochromate, 98%

CAS Number
26299-14-9
Synonyms
PCC

Size Price ($) Quantity Availability
25g 20.61
100g 50.88
500g 166.42
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Pyridinium chlorochromate, 98%

MDL
MFCD00013106
EINECS
247-595-5

Chemical Properties

Formula
C5H6ClCrNO3
Formula Weight
215.56
Melting point
ca 206° dec.
Sensitivity
Moisture Sensitive
Solubility
Soluble in acetone, benzene, dichloromethane, acetonitrile and tetrahydrofuran.

Applications

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.

Notes

Incompatible with alcohols, acetone and methanol.

Literature 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).

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H350-H272-H400-H410-H317

May cause cancer. May intensify fire; oxidizer. Very toxic to aquatic life. Very toxic to aquatic life with long lasting effects. May cause an allergic skin reaction.

Precautionary Statements: P221-P210-P201-P220-P261-P273-P280-P281-P405-P501a

Take any precaution to avoid mixing with combustibles. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Obtain special instructions before use. Keep/Store away from clothing/combustible materials. Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. Use personal protective equipment as required. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,7974
Hazard Class
5.1
Packing Group
II
Harmonized Tariff Code
2933.39
TSCA
Yes

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