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220868 Aldrich

1-Acetoxy-1,3-butadiene

mixture of cis and trans

Synonym: 1,3-Butadienyl acetate

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Properties

Related Categories Building Blocks, C6 to C7, Carbonyl Compounds, Chemical Synthesis, Esters,
vapor pressure   40 mmHg ( 60 °C)
InChI Key   NMQQBXHZBNUXGJ-SNAWJCMRSA-N
contains   0.1% p-tert-butylcatechol as stabilizer
refractive index   n20/D 1.469(lit.)
bp   60-61 °C/40 mmHg(lit.)
density   0.945 g/mL at 25 °C(lit.)
storage temp.   2-8°C

Description

Packaging

10 g in glass bottle

Application

1-Acetoxy-1,3-butadiene was used as diene in the following reactions:
• Diels-Alder reaction with ortho-carbazolequinones to yield benzocarbazolequinone.
• Diels-Alder reaction with diethyl ketovinylphosphonate, with and without Lewis acid assistance.
• Diels-Alder reaction with methyl acrylate to yield racemic forms of 2-hydroxy-3-cyclohexenecarboxylic acid.

It was used for the reaction with dienophiles such as maleimides, a juglone, a butyne-1,4-dione and methyl 2-(4-methylphenyl)-2H-azirine-3-carboxylate and during visible light photocatalysis. It was also used as reactant during intermolecular oxa-Pictet-Spengler cyclization.

General description

1-Acetoxy-1,3-butadiene (1-ABD) can be generated by potassium or sodium acetate catalyzed reaction between crotonaldehyde and acetic anhydride. The product is a mixture of cis and trans forms, that has been confirmed by its physical properties and IR spectra. It is reported to be formed as a major product during the acetoxylation of 1,3-butadiene (BD) in gas-phase in the presence of Pd-KOAc (palladium-potassium acetate) catalyst. 1-ABD participates as 2Π or 4Π diene in cycloaddition reactions. Enantioselective Diels Alder reaction of 2-methoxy-5-methyl-1,4-benzoquinone with 1-ABD in the presence of molecular sieves (mesh size:4Å) has been reported.

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 1992 6.1(3) / PGIII
WGK Germany 
3
RTECS 
EJ1225000
Flash Point(F) 
91.4 °F
Flash Point(C) 
33 °C
Protocols & Articles

Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. Since the reaction involves the formation of a cyclic product vi...
Keywords: Addition reactions, Asymmetric synthesis, Building blocks, Catalysis, Cycloadditions, Diels-Alder reaction, Immobilization

Peer-Reviewed Papers
15

References

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