For chemists engaged in advanced organic synthesis, understanding the potential of specialized intermediates is key to unlocking new molecular designs and efficient reaction pathways. 1-Chloronon-4-yne (CAS 3416-74-8) is one such compound that offers significant versatility, thanks to its unique combination of functional groups. This article explores its chemical reactivity and provides insights for chemists on how to best utilize and source this valuable building block.

The Reactivity Profile of 1-Chloronon-4-yne

1-Chloronon-4-yne, identified by CAS 3416-74-8 and formula C9H15Cl, possesses two primary reactive sites: a terminal alkyne and a primary alkyl chloride. The alkyne group is amenable to a plethora of transformations, including:

  • Click Chemistry: The terminal alkyne can readily participate in copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions to form stable triazole rings, a cornerstone of modern bioconjugation and materials science.
  • Cross-Coupling Reactions: It can undergo Sonogashira couplings with aryl or vinyl halides, a powerful method for carbon-carbon bond formation and extending molecular frameworks.
  • Hydration and Hydrohalogenation: The triple bond can be reacted with water or halogens to introduce carbonyl or vicinal dihalide functionalities, respectively.

The alkyl chloride group, conversely, serves as an excellent electrophile for nucleophilic substitution (SN2) reactions. This allows for the facile introduction of various nucleophiles, such as amines, thiols, alcohols, or organometallic reagents, to the terminal carbon of the nine-carbon chain. This dual reactivity means that 1-chloronon-4-yne can be selectively modified at either end, making it a highly strategic intermediate.

Synthetic Strategies and Applications

Chemists can leverage 1-chloronon-4-yne in multi-step syntheses to build complex molecules. For instance, after performing a Sonogashira coupling on the alkyne, the resulting product can then undergo nucleophilic substitution at the chloride position, or vice-versa. This strategic flexibility is particularly valuable in the synthesis of:

  • Pharmaceutical Intermediates: Designing new drug candidates often requires precise structural modifications, and compounds like 1-chloronon-4-yne offer a scaffold to achieve this.
  • Specialty Polymers: The alkyne group can be used for polymerization or as a site for post-polymerization modification, leading to advanced materials.
  • Agrochemicals: Similar to pharmaceuticals, agrochemical development relies on the precise construction of molecules with specific biological activities.

Sourcing High-Purity 1-Chloronon-4-yne

For the best results in synthesis, it is imperative to buy 1-chloronon-4-yne with high purity, ideally 95% or greater, as is commonly offered by manufacturers. When sourcing, chemists should look for suppliers who provide comprehensive product data, including CAS numbers (3416-74-8) and detailed specifications. Engaging with manufacturers or reputable suppliers, particularly those in China known for their chemical production expertise, can offer access to quality materials at competitive prices. Always verify the supplier's commitment to quality and their ability to provide timely deliveries for your research projects.

In conclusion, the dual reactivity of 1-Chloronon-4-yne makes it a powerful tool for synthetic chemists. By understanding its chemical properties and sourcing it from reliable suppliers, researchers can efficiently incorporate this versatile intermediate into their innovative synthetic endeavors.