1-Hexyne 98%, CAS 693-02-7

1-Hexyne (hex-1-yne, n-butylacetylene) is a six-carbon terminal alkyne with the molecular formula C₆H₁₀ and CAS number 693-02-7. This colorless liquid serves as a versatile building block in organic synthesis, offering unique reactivity through its terminal acetylenic hydrogen and carbon-carbon triple bond. With a molecular weight of 82.14 g/mol and the InChI identifier 1S/C6H10/c1-3-5-6-4-2/h1H,4-6H2,2H3, 1-hexyne represents an essential reagent for researchers developing complex molecular architectures. Premium reagent-grade terminal alkyne for organic synthesis, pharmaceutical development, and materials research.

1-Hexyne is a terminal alkyne featuring a linear six-carbon chain with a triple bond between carbons 1 and 2. The structural formula CH₃(CH₂)₃C≡CH reveals its classification as an aliphatic unsaturated hydrocarbon. This compound appears as a colorless liquid under standard conditions, distinguishing it from its saturated counterpart hexane through its significantly higher reactivity and unique chemical properties.

Chemical Structure & Properties

Physical properties include a melting point of -132°C, positioning 1-hexyne as a liquid across typical laboratory temperature ranges. Vapor pressure characteristics show 253 mm Hg at 37.7°C, indicating significant volatility requiring appropriate handling precautions. The linear geometry imposed by the sp-hybridized carbon atoms creates a rod-like molecular structure with concentrated electron density along the triple bond axis.

Heat capacity values vary with temperature, reflecting the compound’s thermal behavior during processing and storage. The aliphatic unsaturated hydrocarbon classification encompasses its chemical behavior, combining hydrocarbon stability with alkyne reactivity patterns essential for synthetic transformations.

Applications & Uses

1-Hexyne serves critical roles in organic synthesis as a reagent for constructing complex molecular frameworks. Its applications in hydrozirconation and ring-closing metathesis processes enable the formation of cyclic structures and stereoselective transformations valuable in pharmaceutical development. The compound’s use in synthesizing tricyclic isoindolinone scaffolds demonstrates its utility in heterocyclic chemistry.

Industrial chemical manufacturing leverages 1-hexyne’s terminal alkyne functionality for cross-coupling reactions, including Sonogashira couplings with aryl halides. Research applications extend to pharmaceutical development, where the compound serves as a precursor for bioactive molecules and drug intermediates. The acetylenic hydrogen allows metalation reactions, forming organometallic species useful in carbon-carbon bond formation.

Materials research utilizes 1-hexyne in polymer synthesis and surface modification applications. The triple bond provides reactive sites for click chemistry reactions, enabling the construction of functional materials with tailored properties. Advanced organic synthesis employs this compound in multi-step sequences leading to natural product analogs and pharmaceutical targets.