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494992 Sigma-Aldrich

Ethyl 2,3-butadienoate

95%

  • CAS Number 14369-81-4

  • Linear Formula H2C=C=CHCO2C2H5

  • Molecular Weight 112.13

  •  MDL number MFCD01863567

  •  PubChem Substance ID 24872940

  •  NACRES NA.22

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Properties

Related Categories Allenes, Building Blocks, Chemical Synthesis, Organic Building Blocks
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.

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS02  GHS02
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
UN 3272 3 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
116.6 °F - closed cup
Flash Point(C) 
47 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Meet Synthia - Retrosynthesis Sofware
Protocols & Articles

Related Content

Allenes

The past couple of decades have witnessed a surge in the popularity of allenes as viable building blocks for a wide variety of synthetic applications.1 Their versatility allows them to participate in...
Keywords: Addition reactions, Asymmetric synthesis, Building blocks, Catalysis, Cyclizations, Cycloadditions, Cycloisomerizations, Pharmaceutical

Peer-Reviewed Papers
15

References

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