26299-14-9

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;Pyridine·chlorochromic acid;Pyridinium chlorochromate, PCC
• CAS NO: 26299-14-9
• Molecular Formula: C5H6ClCrNO3
• Molecular Weight: 215.56
• EINECS: 247-595-5
• Product Categories: organic intermediates;Pharmaceutical raw material;Imidazoles;Classes of Metal Compounds;Cr (Chromium) Compounds;Oxidation;Pyridinium Compounds;Synthetic Organic Chemistry;Transition Metal Compounds;Pyridine series
• Mol File: 26299-14-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: 205-208 °C(lit.)
• Boiling Point: 115.3 °C at 760 mmHg
• Flash Point: 20 °C
• Appearance: Orange/Crystalline Powder
• Storage Temp.: 2-8°C
• Solubility: Soluble in acetone, benzene, dichloromethane, acetonitrile and t
• Sensitive: Moisture Sensitive
• Stability: Stable. May react with easily oxidized materials. Incompatible with reducing agents, combustible material, metals, strong reduci
• Merck: 14,7974
• BRN: 7054643
• CAS DataBase Reference: Pyridinium chlorochromate(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridinium chlorochromate(26299-14-9)
• EPA Substance Registry System: Pyridinium chlorochromate(26299-14-9)

Safety Data

• Hazard Codes: O,T,N
• 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
• Hazardous Substances Data: 26299-14-9(Hazardous Substances Data)

Usage

Chemical Description

Pyridinium chlorochromate is an oxidizing agent used in organic synthesis.

Chemical Properties

Pyridinium chlorochromate is orange crystalline powder

Uses

Different sources of media describe the Uses of 26299-14-9 differently. You can refer to the following data:
1. 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.
2. Oxidizing agent in organic synthesis. PCC is pyridinium chlorochromate; PDC is pyridinium dichromate. Both are used in dichloromethane.
3. 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.

InChI:InChI=1/C5H5N.ClH.Cr.3O/c1-2-4-6-5-3-1;;;;;/h1-5H;1H;;;;/q;;+1;;;-1/rC5H5N.ClCrO3/c1-2-4-6-5-3-1;1-2(3,4)5/h1-5H;/q;-1/p+1