26299-14-9 Usage
Chemical Description
Pyridinium chlorochromate is an oxidizing agent used in organic synthesis.
Description
Pyridinium chlorochromate (PCC) is an orange crystalline powder that serves as a versatile and selective oxidizing agent in various chemical reactions. It is commonly used in organic synthesis to oxidize primary and secondary alcohols to aldehydes and ketones, respectively, without overoxidation to carboxylic acids.
Uses
Used in Organic Synthesis:
Pyridinium chlorochromate is used as an oxidizing agent for the conversion of primary alcohols to aldehydes and secondary alcohols to ketones. This selective oxidation is particularly useful in the preparation of cyclohexanone, (-)-pulegone, and lactones.
Used in the Preparation of Aromatics:
PCC plays a significant role in the selective mono-oxidation of xylenes to tolualdehydes and the conversion of arylhydroxyamines to nitroso compounds.
Used in the Oxidation of Amino Acids and Related Compounds:
Pyridinium chlorochromate is employed as an oxidant for amino acids, L-cystine, and aniline, making it a valuable tool in the synthesis of various biologically active compounds.
Used in the Oxidation of Alcohols:
PCC is utilized in the oxidation of cycloalkanols, vicinal, and non-vicinal diols, demonstrating its versatility in oxidizing a wide range of alcohols.
Used in the Babler Oxidation Reaction:
Pyridinium chlorochromate is an essential reagent in the Babler oxidation reaction, which is a method for the oxidation of allylic methylene groups.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 26299-14-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,2,9 and 9 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 26299-14:
(7*2)+(6*6)+(5*2)+(4*9)+(3*9)+(2*1)+(1*4)=129
129 % 10 = 9
So 26299-14-9 is a valid CAS Registry Number.
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