Butynone

Butynone
Names
IUPAC name
But-3-yn-2-one
Other names
  • Butyn-2-one
  • Acetylacetylene
  • Methyl ethynyl ketone
  • Acetylethyne
Identifiers
3D model (JSmol)
605353
ChEBI
ChemSpider
ECHA InfoCard 100.014.395 Edit this at Wikidata
EC Number
  • 215-834-2
49292
UNII
  • InChI=1S/C4H4O/c1-3-4(2)5/h1H,2H3
    Key: XRGPFNGLRSIPSA-UHFFFAOYSA-N
  • CC(=O)C#C
Properties
HC2COCH3
Molar mass 116.072 g·mol−1
Boiling point 85 °C (185 °F; 358 K)
Hazards
GHS labelling:
GHS02: Flammable‍GHS06: Toxic‍GHS07: Exclamation mark
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).

Butynone is an organic compound and the simplest ynone. It is a reagent used in organic synthesis as a dienophile and Michael acceptor.

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]

Sources

  1. ^ James A. Marshall, Patrick Eidam, and Hilary Schenck Eidam (2008). "Synthesis of 4-triisopropylsilyl-3-butyn-2-ol by asymmetric transfer hydrogenation". Organic Syntheses. 84: 120{{cite journal}}: CS1 maint: multiple names: authors list (link).
  2. ^ Bagley, Mark; Glover, Christian; Merritt, Eleanor (2007). "The Bohlmann-Rahtz Pyridine Synthesis: From Discovery to Applications". Synlett (16): 2459–2482. doi:10.1055/s-2007-986674.
  3. ^ Bakka, Thomas A.; Strøm, Morten B.; Andersen, Jeanette H.; Gautun, Odd R. (2017). "Methyl propiolate and 3-butynone: Starting points for synthesis of amphiphilic 1,2,3-triazole peptidomimetics for antimicrobial evaluation". Bioorganic & Medicinal Chemistry. 25 (20): 5380–5395. doi:10.1016/j.bmc.2017.07.060. hdl:10037/11419. PMID 28797773.
  4. ^ Jiang, Jingjing; Queneau, Yves; Popowycz, Florence (2023). "Ammonium Acetate Catalyzed Formation of 1,5-Benzodiazepines through [4+2+1] Cycloaddition Involving 5-Hydroxymethylfurfural". European Journal of Organic Chemistry. 26 (19) e202300144. doi:10.1002/ejoc.202300144.

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