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

A11752 Pyridinium chlorochromate, 98%

CAS-Nummer
26299-14-9
Synonyme
PCC

Größe Preis ($) Menge Verfügbarkeit
25g 22,90
100g 51,10
500g 181,00
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Pyridinium chlorochromate, 98%

MDL
MFCD00013106
EINECS
247-595-5

Chemische Eigenschaften

Formel
C5H6ClCrNO3
Molmasse
215.56
Schmelzpunkt
ca 206° dec.
Sensitivität
Moisture Sensitive
Löslichkeit
Soluble in acetone, benzene, dichloromethane, acetonitrile and tetrahydrofuran.

Anwendungen

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.

Bemerkungen

Incompatible with alcohols, acetone and methanol.

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H272-H317-H350

May intensify fire; oxidizer. May cause an allergic skin reaction. May cause cancer.

Sicherheitshinweise: P221-P210v-P201-P220-P261-P280-P363-P308+P313-P405-P501a

Take any precaution to avoid mixing with combustibles. Obtain special instructions before use. Keep/Store away from clothing/combustible materials. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Wash contaminated clothing before reuse. IF exposed or concerned: Get medical advice/attention. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Merck
14,7974
Gefahrenklasse
5.1
Verpackungsgruppe
II
Harmonized Tariff Code
2933.39
TSCA
Yes

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