3-Butyn-2-ol: An Overview of its Chemical Properties and Reactivity
3-Butyn-2-ol, a molecule that elegantly combines an alcohol and an alkyne functional group, is a compound of significant interest in the field of organic chemistry. Its chemical properties and reactivity profile make it a versatile building block for a wide array of synthetic transformations, underpinning its importance in various industries, from pharmaceuticals to materials science. Understanding these characteristics is essential for anyone looking to harness its synthetic potential.
At its core, 3-Butyn-2-ol (C4H6O) is a relatively small molecule with a molecular weight of approximately 70.09 g/mol. Physically, it presents as a transparent, light yellow liquid with a distinct odor. Its boiling point of 66-67°C at 150 mm Hg indicates moderate volatility, while its flash point of 78°F (26°C) classifies it as a flammable liquid. This flammability necessitates careful handling and storage, away from ignition sources, as detailed in safety protocols for this key organic synthesis intermediate.
The reactivity of 3-Butyn-2-ol stems from its two key functional groups. The secondary alcohol moiety can undergo typical alcohol reactions, such as oxidation to a ketone (3-butyn-2-one), esterification with carboxylic acids, or etherification. It can also be protected using various silyl or acyl groups, allowing for selective manipulation of the molecule.
The terminal alkyne group is perhaps even more synthetically valuable. It readily participates in addition reactions, such as hydrohalogenation, hydration, and hydroboration-oxidation, which can convert the alkyne into various functionalized alkenes or ketones. Furthermore, the terminal alkyne is an excellent nucleophile in the presence of a strong base, allowing for its reaction with electrophiles to form new carbon-carbon bonds. This property is fundamental when using 3-Butyn-2-ol as a chemical intermediate.
Moreover, the alkyne functionality is a prime candidate for transition-metal-catalyzed reactions. Click chemistry, specifically the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), is a powerful tool for conjugating 3-Butyn-2-ol to other molecules, forming stable triazole rings. Palladium-catalyzed cross-coupling reactions, such as Sonogashira coupling, also allow for the formation of new carbon-carbon bonds by reacting the terminal alkyne with aryl or vinyl halides. These reactions are widely employed when sourcing high-purity chemicals for advanced synthesis.
The inherent properties of 3-Butyn-2-ol, including its moderate toxicity and potential for polymerization under certain conditions, underscore the need for proper storage and handling. By respecting these chemical characteristics and employing appropriate safety measures, researchers and manufacturers can confidently leverage this acetylenic alcohol to achieve sophisticated synthetic outcomes and buy with confidence.
At its core, 3-Butyn-2-ol (C4H6O) is a relatively small molecule with a molecular weight of approximately 70.09 g/mol. Physically, it presents as a transparent, light yellow liquid with a distinct odor. Its boiling point of 66-67°C at 150 mm Hg indicates moderate volatility, while its flash point of 78°F (26°C) classifies it as a flammable liquid. This flammability necessitates careful handling and storage, away from ignition sources, as detailed in safety protocols for this key organic synthesis intermediate.
The reactivity of 3-Butyn-2-ol stems from its two key functional groups. The secondary alcohol moiety can undergo typical alcohol reactions, such as oxidation to a ketone (3-butyn-2-one), esterification with carboxylic acids, or etherification. It can also be protected using various silyl or acyl groups, allowing for selective manipulation of the molecule.
The terminal alkyne group is perhaps even more synthetically valuable. It readily participates in addition reactions, such as hydrohalogenation, hydration, and hydroboration-oxidation, which can convert the alkyne into various functionalized alkenes or ketones. Furthermore, the terminal alkyne is an excellent nucleophile in the presence of a strong base, allowing for its reaction with electrophiles to form new carbon-carbon bonds. This property is fundamental when using 3-Butyn-2-ol as a chemical intermediate.
Moreover, the alkyne functionality is a prime candidate for transition-metal-catalyzed reactions. Click chemistry, specifically the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), is a powerful tool for conjugating 3-Butyn-2-ol to other molecules, forming stable triazole rings. Palladium-catalyzed cross-coupling reactions, such as Sonogashira coupling, also allow for the formation of new carbon-carbon bonds by reacting the terminal alkyne with aryl or vinyl halides. These reactions are widely employed when sourcing high-purity chemicals for advanced synthesis.
The inherent properties of 3-Butyn-2-ol, including its moderate toxicity and potential for polymerization under certain conditions, underscore the need for proper storage and handling. By respecting these chemical characteristics and employing appropriate safety measures, researchers and manufacturers can confidently leverage this acetylenic alcohol to achieve sophisticated synthetic outcomes and buy with confidence.
Perspectives & Insights
Bio Analyst 88
“The secondary alcohol moiety can undergo typical alcohol reactions, such as oxidation to a ketone (3-butyn-2-one), esterification with carboxylic acids, or etherification.”
Nano Seeker Pro
“It can also be protected using various silyl or acyl groups, allowing for selective manipulation of the molecule.”
Data Reader 7
“It readily participates in addition reactions, such as hydrohalogenation, hydration, and hydroboration-oxidation, which can convert the alkyne into various functionalized alkenes or ketones.”