494992

Ethyl 2,3-butadienoate

95%

• Synonym(s): (Ethoxycarbonyl)allene, Ethyl allenecarboxylate, Ethyl butadienoate
• Linear Formula: H₂C=C=CHCO₂C₂H₅
• CAS Number: 14369-81-4
• Molecular Weight: 112.13
• MDL number: MFCD01863567
• UNSPSC Code: 12352100
• PubChem Substance ID: 24872940
• NACRES: NA.22

Properties

• Assay: 95%
• refractive index: n20/D 1.46 (lit.)
• bp: 80 °C/60 mmHg (lit.)
• density: 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
• InChI key: GLSUOACRAMLJIW-UHFFFAOYSA-N

Description

General description

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.

Application

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.

Safety Information

• Pictograms: GHS02
• Signal Word: Warning
• Hazard Statements: H226
• Precautionary Statements: P210 - P233 - P240 - P241 - P242 - P243
• Hazard Classifications: Flam. Liq. 3
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): 116.6 °F - closed cup
• Flash Point(C): 47 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves