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Cyclopropanecarbonyl chloride
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samir123
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Apr 14, 2025
11:13 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.


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