53963-03-4

Usage

Uses

Used in Organic Synthesis:
1,5-Decadiyne is used as a key intermediate in organic synthesis for the creation of various complex organic molecules. Its reactivity allows for the formation of multiple types of chemical bonds, making it a versatile component in the synthesis of a wide range of compounds.
Used in Polymer Production:
As a monomer, 1,5-Decadiyne is used in the production of polymers. Its ability to form long chains contributes to the development of polymers with specific properties, such as strength, flexibility, or chemical resistance, depending on the desired application.
Used in Pharmaceutical Manufacturing:
1,5-Decadiyne is utilized as a starting material or a building block in the synthesis of pharmaceuticals. Its unique structure can be incorporated into drug molecules to impart specific therapeutic effects or to enhance the drug's pharmacokinetic properties.
Used in Agrochemical Production:
In the agrochemical industry, 1,5-Decadiyne serves as a component in the synthesis of various agrochemicals, including pesticides and herbicides. Its reactivity is harnessed to create compounds that can effectively control or eliminate pests and weeds in agricultural settings.
Used in Electronic Materials:
1,5-Decadiyne is also used in the development of electronic materials, where its properties can be leveraged to create components with specific electrical or optical characteristics, contributing to the advancement of electronic devices and technologies.
Safety and Handling:
Due to its highly reactive nature, 1,5-Decadiyne must be handled with extreme care. It should be stored in a cool, dry place, away from heat and sources of ignition. Appropriate safety measures, including the use of protective equipment, are essential when working with 1,5-Decadiyne to prevent accidents and ensure the safety of personnel.

Upstream product

• 68274-97-5 dec-5-yn-1-ol 
• 628-16-0 hexa-1,5-diyne 

Relevant academic research and scientific papers

SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes

Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C=C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).

Intermediate for Gossyplure, the sex pheromone of the pink bollworm

The sex pheromone of the pink bollworm (Pectinophora gossypiella) is an approximate 1:1 mixture of (Z,Z)- and (Z,E)-7,11-hexadecadienyl acetate; this sex pheromone, the above-identified mixture of isomers, is known as Gossyplure. A component of Gossyplure, (Z,E)-7,11-hexadecadienyl acetate, is the sex pheromone of the Angoumois grain moth (Sitotroga cerealella) and is known as Angoulure. An isomeric component of Gossyplure, the Z,Z isomer, elicits no response from the male Angoumois grain moth and it appears that the relatively large amount of the Z,Z isomer in Gossyplure interferes with the Z,E isomer such that Gossyplure cannot be used as a substitute for Angoulure. The isomeric components of Gossyplure are manufactured by the butylation of the mono-anion of 1,5-hexadiyne to 1,5-decadiyne which is in turn alkylated with hexamethylene halohydrin or a protective derivative thereof, such as tetrahydropyranyl ether, to give the 7,11-hexadecadiynyl moiety which after acetylation and partial reduction affords (Z,Z)-7,11-hexadecadienyl acetate, one of the isomeric components of Gossyplure. The other isomeric component of Gossyplure, the Z,E isomer, which is also known as Angoulure, the sex pheromone of the Angoumois grain moth, is synthesized from deca-(E)-5-enyne, (prepared by sodium-liquid ammonia reduction of 1,5-decadiyne) in an analogous manner.