pyridin-1-ium chlorochromiumoylolate

• ChemBase ID: 74251
• Molecular Formular: C5H6ClCrNO3
• Molecular Mass: 215.55514
• Monoisotopic Mass: 214.94412824
• SMILES: [nH+]1ccccc1.[Cr](=O)(=O)(Cl)[O-]
• Canonical SMILES: c1ccc[nH+]c1.[O-][Cr](=O)(=O)Cl
• InChI: InChI=1S/C5H5N.ClH.Cr.3O/c1-2-4-6-5-3-1;;;;;/h1-5H;1H;;;;/q;;+1;;;-1
• InChIKey: LEHBURLTIWGHEM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pyridin-1-ium chlorochromiumoylolate
• IUPAC Traditional name: pyridium chlorochromiumoylolate
• Synonyms: pyridin-1-ium chlorochromiumoylolate; PCC; Pyridinium chlorochromate; Pyridinium chlorochromate; Pyridinium chlorochromate 98%; 氯铬酸吡啶鎓

Database IDs

• CAS Number: 26299-14-9
• EC Number: 247-595-5
• MDL Number: MFCD00013106
• Merck Index: 147974
• PubChem SID: 162039170
• PubChem CID: 0
• Chemspider ID: 10608386
• Wikipedia Title: Pyridinium_chlorochromate

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 0.6230428
• LogD (pH = 7.4): 0.75354445
• Log P: 0.7555734
• Molar Refractivity: 25.1598 cm^3
• Polarizability: 9.677758 Å^3
• Polar Surface Area: 14.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: soluble in dichloromethane,; benzene, diethyl ether,; acetone, acetonitrile,; THF
• Apperance: orange crystalline powder
• Melting Point: 205°C; 205-208°C°C; ca 206°C dec.

Safety Information

• Storage Warning: Moisture Sensitive; Toxic
• European Hazard Symbols: Nature polluting (N); Oxidising (O); Toxic (T)
• UN Number: UN1479
• Hazard Class: 5.1
• Packing Group: II
• Risk Statements: 49-8-43-50/53; R49, R8, R43, R50/53
• Safety Statements: 53-45-60-61; S53, S45, S60, S61
• TSCA Listed: 是
• GHS Pictograms: GHS03; GHS07; GHS08; GHS09
• Main Hazard: Poison, contact hazard, inhalation hazard, enviromental hazard, carcinogenic, irritant
• NFPA704:
  

  3

  3
• GHS Hazard statements: H350-H272-H400-H410-H317
• GHS Precautionary statements: P221-P210-P302+P352-P321-P405-P501A

Product Information

• Purity: 98%
• Salt Data: GrO3Cl-

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).