1-Acetoxy-1,3-butadiene, mixture of cis and trans

Code: 220868-10G D2-231

Application

1-Acetoxy-1,3-butadiene was used as diene in the following reactions:Diels-Alder reaction with ortho-carbazolequinones to yield benzocarbazolequinone.Die...


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€171.00 10G
€210.33 inc. VAT

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.

Packaging

10 g in glass bottle

bp60-61 °C/40 mmHg (lit.)
contains0.1% p-tert-butylcatechol as stabilizer
density0.945 g/mL at 25 °C (lit.)
formliquid
InChI keyNMQQBXHZBNUXGJ-SNAWJCMRSA-N
InChI1S/C6H8O2/c1-3-4-5-8-6(2)7/h3-5H,1H2,2H3/b5-4+
Quality Level100
refractive indexn20/D 1.469 (lit.)
SMILES stringCC(=O)OC=CC=C
storage temp.2-8°C
vapor pressure40 mmHg ( 60 °C)
Cas Number1515-76-0
Hazard Class3
Un Number1992
Pack GroupIII
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