494992

Ethyl-2,3-butadienoat

95%

• Synonym(e): (Ethoxycarbonyl)allene, Ethyl allenecarboxylate, Ethyl butadienoate
• Lineare Formel: H₂C=C=CHCO₂C₂H₅
• CAS-Nummer: 14369-81-4
• Molekulargewicht: 112.13
• MDL-Nummer: MFCD01863567
• UNSPSC-Code: 12352100
• PubChem Substanz-ID: 24872940
• NACRES: NA.22

Eigenschaften

• Assay: 95%
• Brechungsindex: n20/D 1.46 (lit.)
• bp: 80 °C/60 mmHg (lit.)
• Dichte: 0.966 g/mL at 25 °C (lit.)
• SMILES String: [H]C([H])=C=C([H])C(=O)OCC
• InChI: 1S/C6H8O2/c1-3-5-6(7)8-4-2/h5H,1,4H2,2H3
• InChIKey: GLSUOACRAMLJIW-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

Ethyl 2,3-butadienoate is an α-allenic ester. The reaction of ethyl 2,3-butadienoate with N-tosylated imines in the presence of DABCO (1,4-diazabicyclo[2.2.2]octane) or DMAP (4-dimethylaminopyridine) forms azetidine derivatives or novel dihydropyridine derivatives respectively. The performance of bifunctional N-acyl aminophosphines to catalyze the asymmetric [3+2] cycloaddition of phenylidenemalononitrile with ethyl 2,3-butadienoate has been evaluated.

Anwendung

Ethyl 2,3-butadienoate may be used in the synthesis of dihydropyrans by reacting with acyclic enones. It may also be used to synthesize spiranic heterocycles by reacting with heterocyclic bis-arylidene ketones via phosphine-catalyzed [3+2] annulations.

Sicherheitshinweise

• Piktogramme: GHS02
• Signalwort: Warning
• H-Sätze: H226
• P-Sätze: P210 - P233 - P240 - P241 - P242 - P243
• Gefahreneinstufungen: Flam. Liq. 3
• Lagerklassenschlüssel: 3 - Flammable liquids
• WGK: WGK 3
• Flammpunkt (°F): 116.6 °F - closed cup
• Flammpunkt (°C): 47 °C - closed cup
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter