494992
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:
Molecular Weight:
112.13
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
95%
Quality Segment
assay
95%
refractive index
n
bp
80 °C/60 mmHg (lit.)
density
0.966 g/mL at 25 °C (lit.)
functional group
ester
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.
signalword
Warning
hcodes
Hazard Classifications
Flam. Liq. 3
Storage Class
3 - Flammable liquids
wgk
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
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