Pyridinium Dichromate(PDC) (CAS 20039-37-6)

Key Physical Properties:

  • Appearance:Orange to brown powder, crystals, or chunks.
  • Physical State:Solid at room temperature (20°C).
  • Melting Point:Around 152-153 °C (literature values).
  • Solubility:Soluble in water.
  • Sensitivity:Hygroscopic (absorbs moisture from the air).
  • Molecular Formula:C₁₀H₁₂N₂·Cr₂O₇ (often shown as (C₅H₅NH)₂Cr₂O 7).
  • Molecular Weight:21 g/mol.
  • Density:71𝑔/𝑐𝑚3at 20 °C.
  • Solubility:
  • Soluble in: Water, Dimethylformamide (DMF) (0.9 g/mL at 25 °C), and Dimethyl sulfoxide (DMSO).
  • Slightly Soluble in: Acetone and Dichloromethane (DCM).
  • Insoluble in: Toluene, Ether, Hexane, and Ethyl acetate.
  • Hygroscopy: The substance is hygroscopic, meaning it readily absorbs moisture from the air.
  • Vapor Pressure: 0 Pa at 25 °C.

Uses

  • Organic Synthesis: Oxidizes primary alcohols to aldehydes, secondary alcohols to ketones, and is useful in forming esters and enones, often with tert-butyl hydroperoxide.
  • Dye Synthesis: Acts as an intermediate in creating dyes.
  • Pharmaceutical Research: Helps synthesize complex molecules for drug discovery.
  • Material Science: Used in developing advanced materials, polymers, and coatings.
  • Analytical Chemistry: Employed in analytical methods for detecting organic compounds.
  • Environmental Studies:Researched for understanding chromium’s environmental impact.

 

Why it’s Used:

  • It’s a selective oxidant, allowing specific transformations without affecting other functional groups.
  • It’s a pyridinium salt, offering unique reactivity in organic reactions. 

Key Applications:

  • Alcohol Oxidation:Converts primary alcohols to aldehydes and secondary alcohols to ketones, often with better selectivity than other chromium reagents.
  • Selective Oxidation:Oxidizes allylic alcohols in the presence of other alcohol groups, notes Adi Chemistry.
  • Synthesis of Esters & Enones:Oxidizes acetals to esters and didehydroketones to enones with co-oxidants like tert-butyl hydroperoxide, says Sigma-Aldrich.
  • Organic Synthesis:Used in developing new drugs (pharmaceuticals), creating dyes, and synthesizing complex organic structures.
  • Material Science:Contributes to the creation of advanced coatings and polymers,
  • Analytical Chemistry:Helps in detecting and quantifying specific compounds, according to

In essence, PDC (20039-37-6) is a versatile reagent for fine-tuning chemical structures in advanced chemical research and manufacturing.

Primary Chemical Applications

The most common use of PDC is the selective oxidation of alcohols into carbonyl compounds. Its reactivity often depends on the solvent used:

  • Alcohol Oxidation: It converts primary alcohols to aldehydes and secondary alcohols to ketones.
  • Selective Solvent Effects: In dichloromethane (𝐶𝐻2𝐶𝑙2), it stops at the aldehyde stage for primary alcohols; however, in N,N-dimethylformamide (DMF), it can further oxidize primary alcohols to carboxylic acids.
  • Acetal Conversion: It is used to convert acetals into esters.
  • Enone Synthesis: In the presence of tert-butyl hydroperoxide, it can convert didehydroketones to enones.
  • Other Oxidations: It plays a role in oxidizing unsaturated tertiary alcohols, silyl ethers, oximes, and the carbon-boron bond.

Research and Industrial Applications

  • Pharmaceutical Synthesis: PDC is a key reagent in the synthesis of complex molecules for drug discovery and development.
  • Specialized Molecule Protection: It is often preferred over similar reagents like PCC (Pyridinium chlorochromate) for oxidizing “fragile” molecules, such as nucleosides and carbohydrates, because it is less acidic.
  • Material Science: Used in developing advanced materials, including specialized coatings and polymers.
  • Environmental & Analytical Chemistry: Employed in studies regarding chromium’s environmental impact and as a reagent for the detection and quantification of specific organic compounds.

Potential Future Applications

Recent research suggests potential pharmacological roles for PDC derivatives, including:

  • Enzyme Inhibition: Investigated for inhibiting the COX-2 enzyme by binding to its active site.
  • Therapeutic Potential: Studied for possible applications in treating autoimmune diseases like rheumatoid arthritis and chronic bronchitis, though these are not standard clinical uses.

 

 

FAQs

What is the CAS number of Pyridinium Dichromate (PDC)?

The CAS number of Pyridinium Dichromate (PDC) is 20039-37-6.

What are the main uses of Pyridinium Dichromate (PDC) (20039-37-6)?

Pyridinium Dichromate (PDC) (20039-37-6) is mainly used to oxidize primary and secondary alcohols to aldehydes and ketones in organic synthesis.

What is the molecular formula of Pyridinium Dichromate (PDC) (20039-37-6)?

The molecular formula of Pyridinium Dichromate (PDC) (20039-37-6) is C₁₀H₁₀Cr₂N₂O₇.

What is the appearance of Pyridinium Dichromate (PDC)?

Pyridinium Dichromate (PDC) (20039-37-6) appears as an orange to reddish crystalline solid.

Is Pyridinium Dichromate (PDC) moisture sensitive?
Pyridinium Dichromate (PDC) (20039-37-6) is moderately moisture sensitive and should be kept in tightly sealed containers.

FAQs

What is the CAS number of Pyridinium Dichromate (PDC)?

The CAS number of Pyridinium Dichromate (PDC) is 20039-37-6.

What are the main uses of Pyridinium Dichromate (PDC) (20039-37-6)?

Pyridinium Dichromate (PDC) (20039-37-6) is mainly used to oxidize primary and secondary alcohols to aldehydes and ketones in organic synthesis.

What is the molecular formula of Pyridinium Dichromate (PDC) (20039-37-6)?

The molecular formula of Pyridinium Dichromate (PDC) (20039-37-6) is C₁₀H₁₀Cr₂N₂O₇.

What is the appearance of Pyridinium Dichromate (PDC)?

Pyridinium Dichromate (PDC) (20039-37-6) appears as an orange to reddish crystalline solid.

Is Pyridinium Dichromate (PDC) moisture sensitive?
Pyridinium Dichromate (PDC) (20039-37-6) is moderately moisture sensitive and should be kept in tightly sealed containers.