samir12
32 posts
Apr 14, 2025
9:44 PM
|
Introduction
Cyclopropanecarbonyl chloride
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.
|
