Pyridinium chlorochromate Chemical Properties

Melting point:

205-208 °C(lit.)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in acetone, benzene, dichloromethane, acetonitrile and tetrahydrofuran.

form 

Crystalline Powder

color 

Orange

Sensitive 

Moisture Sensitive

Merck 

14,7974

BRN 

7054643

Exposure limits

OSHA: Ceiling 0.1 mg/m3
NIOSH: IDLH 15 mg/m3; TWA 0.0002 mg/m3

Stability:

Stable. May react with easily oxidized materials. Incompatible with reducing agents, combustible material, metals, strong reducing agents.

InChI

InChI=1S/C5H5N.ClH.Cr.3O/c1-2-4-6-5-3-1;;;;;/h1-5H;1H;;;;

InChIKey

LEHBURLTIWGHEM-UHFFFAOYSA-N

SMILES

C1=CC=NC=C1.[Cr](=O)(=O)(=O)[Cl-].[H+]

CAS DataBase Reference

26299-14-9(CAS DataBase Reference)

EPA Substance Registry System

Pyridinium chlorochromate (26299-14-9)

Safety Information

Hazard Codes 

O,T,N

Risk Statements 

49-8-43-50/53-20/21/22

Safety Statements 

53-45-60-61-37-24-17-44-36/37/39-22

RIDADR 

UN 1479 5.1/PG 2

WGK Germany 

2

TSCA 

Yes

HazardClass 

5.1

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:Pyridinium chlorochromate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Pyridinium chlorochromate Usage And Synthesis

Chemical Properties

Pyridinium chlorochromate is orange crystalline powder

Uses

Oxidizing agent in organic synthesis.
PCC is pyridinium chlorochromate; PDC is pyridinium dichromate. Both are used in dichloromethane.

Uses

Pyridinium chlorochromate is usually used to oxidize an allylic methylene group.
Oxidation of primary alcohols to aldehydes

Pyridinium dichromate (PDC) or pyridinium chlorochromate (PCC) in anhydrous media such as dichloromethane oxidizes primary alcohols to aldehydes while avoiding overoxidation to carboxylic acids.

Uses

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.

Reactions

Pyridinium chlorochromate (PCC) is a widespread used oxidation reagent but lacks of selectivity with unsaturated compounds. Furthermore, the workup procedure is quite tedious. Absorption of PCC onto silica gel improves the oxidation but then a reagent excess is necessary to reach appropriate rates. These drawbacks can be overcome by sonication leading to short reaction times and only an small excess of 1.2.-1.5 eq. of PCC is required. Using this reagent has been used to oxidise borneol to camphor in 85% yield.

Purification Methods

Dry it in a vacuum for 1hour. It is not hygroscopic and can be stored for extended periods at room temperature without change. If the purity is very suspect, it can be readily prepared. [Corey & Scuggs Tetrahedron Lett 2647 1975, Piancatelli et al. Synthesis 245 1982.] (Possible CARCINOGEN.) § Available commercially on a polymer support.

Pyridinium chlorochromate(26299-14-9)Related Product Information

• 2-Chloro-3-cyanopyridine
• 2-Chloro-5-chloromethylpyridine
• Pentachloropyridine
• Clopidol
• Pyridine
• Potassium chromate
• Pyridinium dichromate
• Chromate, Ion chromatography standard solution, Specpure, CrO4ˉ2 1000μg/ml
• Chromium(VI) oxide
• CHROMIUM (III) OXIDE HYDRATE
• PCC ON SILICA GEL
• 2,2'-BIPYRIDINIUM CHLOROCHROMATE
• 4-(DIMETHYLAMINO)PYRIDINIUM CHLOROCHROMA TE, 97%
• Chromium
• QUINOLINIUM CHLOROCHROMATE
• Dichromate, Ion chromatography standard solution, Specpure, Cr2O7ˉ2 1000μg/ml
• Pyridinium chlorochromate
• SI-PYRIDINIUM CHLOROCHROMATE