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494992

Sigma-Aldrich

Ethyl 2,3-butadienoate

95%

Synonym(s):

(Ethoxycarbonyl)allene, Ethyl allenecarboxylate, Ethyl butadienoate

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About This Item

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

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

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.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

116.6 °F - closed cup

flash_point_c

47 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Abnormal aza-Baylis-Hillman reaction of N-tosylated imines with ethyl 2,3-butadienoate and penta-3,4-dien-2-one.
Zhao GL, et al.
Organic Letters, 5(24), 4737-4739 (2003)
Asymmetric [3+2] Cycloadditions of Allenoates and Dual Activated Olefins Catalyzed by Simple Bifunctional N-Acyl Aminophosphines.
Xiao H, et al.
Angewandte Chemie (International Edition in English), 49(26), 4467-4470 (2010)
Development of a formal catalytic asymmetric [4+2] addition of ethyl-2,3-butadienoate with acyclic enones.
Ashtekar KD, et al.
Organic Letters, 13(21), 5732-5735 (2011)
Heterocyclic Spiranes and Dispiranes via Enantioselective Phosphine-Catalyzed [3+2] Annulations.
Duvvuru D, et al.
Advanced Synthesis & Catalysis, 354(2-3), 408-414 (2012)

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