Butynone
Chemical compound
From Wikipedia, the free encyclopedia
Butynone is an organic compound and the simplest ynone. It is a reagent used in organic synthesis as a dienophile and Michael acceptor.
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| Names | |
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| IUPAC name
But-3-yn-2-one | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| 605353 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.014.395 |
| EC Number |
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| 49292 | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| HC2COCH3 | |
| Molar mass | 116.072 g·mol−1 |
| Boiling point | 85 °C (185 °F; 358 K) |
| Hazards | |
| GHS labelling: | |
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| Danger | |
| H225, H300, H315, H319, H335 | |
| P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P310+P330, P303+P361+P353, P304+P340+P312, P305+P351+P338, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501 | |
| Safety data sheet (SDS) | Sigma-Aldrich Co., product no. 161314. |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
The triisopropylsilyl derivative of butynone is prepared by oxidation of the corresponding derivative of 2-butynol, itself prepared from TIPS acetylene by deprotonation followed by nucleophilic addition to acetaldehyde.[1]
Applications
Butynone was one of the reagents used in the discovery of the Bohlmann–Rahtz pyridine synthesis.[2]
Butynone and its derivatives participate in cycloaddition reactions, yielding a variety of heterocycles. The electron-deficient alkyne group participates in the azide-alkyne Huisgen cycloaddition to produce 1,2,3-triazine methyl ketones.[3] [4+2+1] cycloaddition with 1,2-phenylenediamine and furfural derivatives gives benzodiazepine rings.[4]