How Propargyl Chloride 85% in DMF Enhances Synthetic Versatility in Organic Chemistry
Introduction
Propargyl Chloride 85% in DMF is a highly reactive alkyne-based alkylating agent widely used in organic synthesis, pharmaceutical development, and advanced material chemistry. Dissolved in dimethylformamide (DMF) to improve handling and reactivity, this formulation allows for safe, efficient, and controlled reactions, especially in environments requiring strong electrophilic intermediates.
Chemical Identity
| Name | Propargyl Chloride (85% in DMF) |
|---|---|
| CAS Number | 624-65-7 (pure compound) |
| Molecular Formula | C₃H₃Cl |
| Structure | HC≡C–CH₂Cl |
| Physical Form | Colorless to pale yellow solution |
| Solvent | DMF (Dimethylformamide, 15%) |
Key Features
Highly reactive propargyl group: Enables nucleophilic substitution, cycloaddition, and coupling reactions.
Stable and pre-diluted: 85% in DMF provides a safer alternative to handling neat propargyl chloride.
Broad compatibility: Reacts with alcohols, thiols, amines, and other nucleophiles.
Facilitates click chemistry: Ideal for synthesis involving azide-alkyne cycloaddition (CuAAC).
Applications
| Industry | Use |
|---|---|
| Pharmaceuticals | Intermediate for APIs, alkylation of heterocycles |
| Agrochemicals | Used in synthesis of pesticides and herbicide candidates |
| Polymer Chemistry | Propargylation of resins, coatings, and photoresists |
| Materials Science | Cross-linking agent for functional polymers and dendrimers |
| Flavors/Fragrances | Used in developing complex molecules through alkylation |
Reactivity & Mechanism
Acts as a strong electrophile at the methylene carbon (–CH₂Cl).
Undergoes SN2 substitution with a wide variety of nucleophiles.
The terminal alkyne can be preserved or further functionalized (e.g., Sonogashira coupling).
Example Reaction:
Alcohol + Propargyl Chloride → Propargyl Ether
Amine + Propargyl Chloride → Propargylated Amine (precursor to click reaction)
Advantages of DMF Solution Form
Improved handling – reduces volatility and inhalation risks of neat propargyl chloride.
Higher precision in reaction scaling – consistent concentration allows controlled dosing.
Solubility benefits – DMF dissolves a wide range of organic reagents for homogeneous reactions.
Handling and Storage
Toxic and corrosive – handle under fume hood with protective gloves and goggles.
Moisture-sensitive – store in tightly sealed containers, away from water and acids.
Storage temperature: 2–8°C for optimal shelf life.
Frequently Asked Questions
Q: Can this be used in microwave-assisted synthesis?
A: Yes. Its high reactivity and DMF solvent compatibility make it suitable for microwave-assisted alkylation and click chemistry.
Q: Is it suitable for industrial-scale production?
A: Absolutely. The pre-diluted form supports safer large-scale use, especially with appropriate containment.
Q: What is the shelf life of the DMF solution?
A: When properly stored, it maintains stability for 6–12 months without significant degradation.
Conclusion
Propargyl Chloride 85% in DMF is a versatile, high-performance reagent offering efficient propargylation, compatibility with a variety of synthetic techniques, and safer handling. It empowers chemists in drug discovery, advanced materials, and fine chemical manufacturing to streamline complex transformations with precision and control.
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