CYCLOPROPANECARBONYL CHLORIDE (CPCC): A KEY INTERMEDIATE IN ORGANIC SYNTHESIS

Cyclopropanecarbonyl Chloride (CPCC): A Key Intermediate in Organic Synthesis

Cyclopropanecarbonyl Chloride (CPCC): A Key Intermediate in Organic Synthesis

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Introduction


Cyclopropanecarbonyl chloride (CPCC) is a valuable reagent in organic and medicinal chemistry, particularly for the synthesis of complex pharmaceutical compounds and advanced materials. Known for its reactive acid chloride group and strained cyclopropane ring, CPCC plays a crucial role in introducing the cyclopropylcarbonyl moiety into various chemical structures, enhancing biological activity and structural diversity.





Chemical Identity



  • IUPAC Name: Cyclopropanecarbonyl chloride

  • Other Names: CPCC, Cyclopropylcarbonyl chloride

  • Molecular Formula: C4H5ClO

  • Molecular Weight: 104.53 g/mol

  • CAS Number: 4023-34-1

  • Appearance: Clear to pale yellow liquid

  • Boiling Point: ~130-132 °C

  • Density: ~1.14 g/cm³







Structure and Reactivity


Cyclopropanecarbonyl chloride consists of a cyclopropane ring attached to a carbonyl chloride group. The ring strain in cyclopropane makes the molecule more reactive, while the acid chloride group serves as a key functional handle for acylation reactions.

It readily reacts with:

  • Amines to form cyclopropanecarboxamides

  • Alcohols to form esters

  • Hydrazines and hydroxylamines for various heterocyclic transformations







Applications of CPCC


1. Pharmaceutical Intermediate


CPCC is widely used in the synthesis of cyclopropyl-containing drugs, especially those requiring the cyclopropylcarbonyl group for increased metabolic stability and bioactivity. It serves as a precursor in:

  • Antiviral drugs

  • Antibacterial agents

  • Anti-inflammatory compounds


2. Agrochemical Synthesis


Cyclopropyl moieties are common in agrochemicals, where they enhance lipophilicity and membrane penetration. CPCC is employed in synthesizing:

  • Herbicides

  • Insecticides

  • Fungicides


3. Specialty Chemicals and Materials


Due to its unique ring strain, CPCC finds use in polymer chemistry and materials science, contributing to novel monomers and structural motifs.

4. Peptide and Protein Modification


In peptide chemistry, CPCC can be used for selective N-acylation, adding structural rigidity and lipophilicity to bioactive peptides.





Handling and Storage



  • Store in cool, dry, and well-ventilated conditions

  • Keep away from moisture and open flames

  • Use proper PPE (gloves, goggles, lab coat)

  • Best handled under inert atmosphere (e.g., nitrogen or argon)







Safety and Regulatory Information



  • Hazard Class: Corrosive, Irritant

  • Hazard Statements: Causes skin burns and eye damage; harmful if inhaled

  • First Aid Measures: In case of contact, rinse with water for 15+ minutes; seek medical attention

  • Regulatory Compliance: Follow local and international chemical handling and transportation regulations







Conclusion


Cyclopropanecarbonyl chloride (CPCC) is a highly useful chemical intermediate with wide-ranging applications in pharmaceuticals, agrochemicals, and fine chemical synthesis. Its dual functionality — the reactive acyl chloride group and the strained cyclopropane ring — provides enhanced reactivity and structural benefits to the final products.

Looking to procure CPCC? Reach out to us for bulk quantities, technical data sheets (TDS), MSDS, and global shipping options tailored to your research or production needs.

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