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Pyridinium chlorochromate

Pyridinium chlorochromate Basic information
Product Name:Pyridinium chlorochromate
Synonyms:PCC;PYRIDINIUM CHLOROCHROMATE;chromate(1-),chlorotrioxo-,(beta-4)-,hydrogen,compd.withpyridine(1:1);Pyridine, (T-4)-chlorotrioxochromate(1-);Pyridine, chlorotrioxochromate(1-);Urine Luck;pyridinium;PYRIDINIUM CHLOROCHROMATE, CA. 20 WT. % ON BASIC ALUMINA
CAS:26299-14-9
MF:C5H6ClCrNO3
MW:215.55
EINECS:247-595-5
Product Categories:Pharmaceutical raw material;organic intermediates;Classes of Metal Compounds;Cr (Chromium) Compounds;Oxidation;Imidazoles;Pyridinium Compounds;Synthetic Organic Chemistry;Transition Metal Compounds;Pyridine series
Mol File:26299-14-9.mol
Pyridinium chlorochromate Structure
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 limitsOSHA: 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.
InChIKeyLEHBURLTIWGHEM-UHFFFAOYSA-N
CAS DataBase Reference26299-14-9(CAS DataBase Reference)
EPA Substance Registry SystemPyridinium 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 Information
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Pyridinium chlorochromate Usage And Synthesis
Chemical PropertiesPyridinium chlorochromate is orange crystalline powder
UsesPyridinium chlorochromate is usually used to oxidize an allylic methylene group.
Oxidation of primary alcohols to aldehydes
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.


UsesOxidizing agent in organic synthesis.
PCC is pyridinium chlorochromate; PDC is pyridinium dichromate. Both are used in dichloromethane.
UsesPyridinium 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.
ReactionsPyridinium 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.
Pyridinium chlorochromate Reaction
Purification MethodsDry 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 Preparation Products And Raw materials
Preparation Products3-(TRIFLUOROMETHYL)-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE-->1,3-DIMETHYL-1H-PYRAZOLE-5-CARBALDEHYDE-->Tetrahydropyran-4-carbaldehyde-->3-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOLE-4-CARBALDEHYDE-->1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBALDEHYDE-->Cyclopropanecarboxaldehyde-->3-(2-METHOXY-PHENYL)-PROPIONALDEHYDE-->1-(2,6-DIFLUOROPYRIDIN-3-YL)PROPAN-1-ONE-->2-(4-Methylpiperazin-1-yl)-6-(trifluoromethyl)pyrimidine-4-carbaldehyde-->5-CHLORO INDAZOLE-3-CARBOXALDEHYDE-->3-(4-NITRO-PHENYL)-PROPIONALDEHYDE-->4-(MORPHOLIN-4-YLMETHYL)-1,3-THIAZOL-2-AMINE-->1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde-->3-(2,6-DICHLOROPHENYL)-5-METHYLISOXAZOLE-4-CARBALDEHYDE-->2,5-DIBROMONICOTINALDEHYDE-->TERT-BUTYL 4-(4-FORMYL-1,3-THIAZOL-2-YL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE-->TERT-BUTYL 4-(5-FORMYL-4-METHYL-1,3-THIAZOL-2-YL)PIPERIDINE-1-CARBOXYLATE-->,5-Dihydro-5-methyl-6-[4-(4-oxo-1(4H)-pyridinyl)phenyl]-1,2,4-triazin-3(2H)-one-->2-PHENYL-1,3-THIAZOLE-4-CARBALDEHYDE-->TERT-BUTYL 4-(5-FORMYLPYRID-2-YL)PIPERAZINE-1-CARBOXYLATE-->2,4-DIPHENYL-1,3-THIAZOLE-5-CARBALDEHYDE-->N-BOC-L-Prolinal-->2-[4-(TRIFLUOROMETHYL)PHENYL]-1,3-THIAZOLE-4-CARBALDEHYDE-->4-METHYL-2-[4-(TRIFLUOROMETHYL)PHENYL]-1,3-THIAZOLE-5-CARBALDEHYDE
Pyridinium dichromate PYRIDINIUM CHLOROCHROMATE POLYMER BOUND, 100-200 MESH,PYRIDINIUM CHLOROCHROMATE POLYMER BOUND 2-Chloro-3-cyanopyridine SI-PYRIDINIUM CHLOROCHROMATE 2-Chloro-5-chloromethylpyridine QUINOLINIUM CHLOROCHROMATE PCC ON SILICA GEL 2,2'-BIPYRIDINIUM CHLOROCHROMATE PYRIDINIUM CHLOROCHROMATE CA. 20% ON S& Pyridinium chlorochromate Chromium(VI) oxide Pentachloropyridine Dichromate, Ion chromatography standard solution, Specpure, Cr2O7ˉ2 1000μg/ml Potassium chromate CHROMIUM (III) OXIDE HYDRATE Chromate, Ion chromatography standard solution, Specpure, CrO4ˉ2 1000μg/ml Clopidol Pyridine
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