| Identification | More | [Name]
Pyridinium chlorochromate | [CAS]
26299-14-9 | [Synonyms]
PCC
PYRIDINIUM CHLOROCHROMATE
chromate(1-),chlorotrioxo-,(beta-4)-,hydrogen,compd.withpyridine(1:1)
pyridinium
PYRIDINIUM CHLOROCHROMATE, CA. 20 WT. % ON BASIC ALUMINA
PyridiniumChlirochromate
PyridinumChlorochromate
PyridiniumChlorochromate99%
Pyridinium Chlorochromate 99%
Pyridiniumchlorochromate,98%
Chromate(1-), chlorotrioxo-, (T-4)-, hydrogen, compd. with pyridine (1:1)
Chromate(1-), chlorotrioxo-, (T-4)-, hydrogen, compound with pyridine (1:1)
Corey's reagent
Pyridine, (T-4)-chlorotrioxochromate(1-)
Pyridine, chlorotrioxochromate(1-)
Urine Luck
Pyridine·chlorochromic acid
Pyridinium chlorochromate, PCC | [EINECS(EC#)]
247-595-5 | [Molecular Formula]
C5H6ClCrNO3 | [MDL Number]
MFCD00013106 | [Molecular Weight]
215.56 | [MOL File]
26299-14-9.mol |
| Chemical Properties | Back Directory | [Appearance]
orange crystalline powder | [Melting point ]
205-208 °C(lit.)
| [storage temp. ]
2-8°C | [solubility ]
Soluble in acetone, benzene, dichloromethane, acetonitrile and tetrahydrofuran. | [form ]
Crystalline Powder | [color ]
Orange | [Stability:]
Stable. May react with easily oxidized materials. Incompatible with reducing agents, combustible material, metals, strong reducing agents. | [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 | [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]
26299-14-9(EPA Substance) |
| Questions And Answer | Back Directory | [Synthesis]
The common method is to react chromium trioxide with hydrochloric acid to produce chlorochromic acid, followed by the addition of pyridine at 0 °C to obtain a stable orange-yellow Pyridinium chlorochromate solid: 
Specific reaction steps: Under stirring, chromium trioxide (100 g, 1 mol) is rapidly added to 6 N hydrochloric acid (184 mL, 1.1 mol). After 5 minutes, when the homogeneous solution has cooled to 0 °C, pyridine (79.1 g, 1 mol) is carefully added over a period of more than 10 minutes. The solution is recooled to 0 °C, yielding an orange-yellow solid. The solid is collected in a sintered glass funnel, filtered, and vacuum dried for 1 hour, yielding 250.5 g, 54% . |
| Safety Data | Back Directory | [Symbol(GHS) ]
   
GHS03,GHS07,GHS08,GHS09 | [Signal word ]
Danger | [Hazard statements ]
H272-H317-H350i-H410 | [Precautionary statements ]
P201-P210-P273-P280-P302+P352-P308+P313 | [Hazard Codes ]
O,T,N | [Risk Statements ]
R49:May cause cancer by inhalation.
R8:Contact with combustible material may cause fire.
R43:May cause sensitization by skin contact.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S37:Wear suitable gloves .
S24:Avoid contact with skin .
S17:Keep away from combustible material .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [RIDADR ]
UN 1479 5.1/PG 2
| [WGK Germany ]
2
| [TSCA ]
Yes | [HazardClass ]
5.1 | [PackingGroup ]
III | [HS Code ]
29333990 | [Storage Class]
5.1B - Oxidizing hazardous materials | [Hazard Classifications]
Aquatic Acute 1
Aquatic Chronic 1
Carc. 1B Inhalation
Ox. Sol. 2
Skin Sens. 1 |
| Raw materials And Preparation Products | Back Directory | [Preparation Products]
3-(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 |
| Hazard Information | Back Directory | [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.
| [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.
| [reaction suitability]
reagent type: oxidant | [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. |
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Alfa Aesar
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Energy Chemical
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Jia Xing Isenchem Co.,Ltd
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