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220868

Sigma-Aldrich

1-Acetoxy-1,3-butadiene

mixture of cis and trans

Synonyme(s) :

1,3-Butadienyl acetate

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About This Item

Formule linéaire :
CH2=CHCH=CHOCOCH3
Numéro CAS:
1515-76-0
Poids moléculaire :
112.13
Numéro Beilstein :
1743394
Numéro MDL:
MFCD00008714
Code UNSPSC :
12352100
ID de substance PubChem :
24853196
Nomenclature NACRES :
NA.22

Pression de vapeur

40 mmHg ( 60 °C)

Niveau de qualité

100

Forme

liquid

Contient

0.1% p-tert-butylcatechol as stabilizer

Indice de réfraction

n20/D 1.469 (lit.)

Point d'ébullition

60-61 °C/40 mmHg (lit.)

Densité

0.945 g/mL at 25 °C (lit.)

Température de stockage

2-8°C

Chaîne SMILES 

CC(=O)O\C=C\C=C

InChI

1S/C6H8O2/c1-3-4-5-8-6(2)7/h3-5H,1H2,2H3/b5-4+

Clé InChI

NMQQBXHZBNUXGJ-SNAWJCMRSA-N

Description générale

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.

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.

Pictogrammes

FlameSkull and crossbones
GHS02,GHS06

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

91.4 °F - closed cup

Point d'éclair (°C)

33 °C - closed cup

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Methyl 2-(4-methylphenyl)-2H-azirine-3-carboxylate as dienophile in hetero-Diels-Alder cycloaddition: a DFT approach
P. Sharma, et al.
Letters in Organic Chemistry, 8, 132-137 (2011)
Synthesis and absolute configuration of the isomers of homoisocitric acid (1-hydroxy-1,2,4-butanetricarboxylic acid) and the stereochemistry of lysine biosynthesis.
K Chilina et al.
Biochemistry, 8(7), 2846-2855 (1969-07-01)
Shishi Lin et al.
Journal of the American Chemical Society, 133(48), 19350-19353 (2011-10-29)
Ruthenium(II) polypyridyl complexes promote the efficient radical cation Diels-Alder cycloaddition of electron-rich dienophiles upon irradiation with visible light. These reactions enable facile [4 + 2] cycloadditions that would be electronically mismatched under thermal conditions. Key to the success of this
The Journal of Organic Chemistry, 58, 7146-7146 (1993)
Cis and trans 1-acetoxy-1, 3-butadiene: physical and chemical properties, infrared and ultraviolet spectra.
Georgieff KK and Dupre A.
Canadian Journal of Chemistry, 38(7), 1070-1075 (1960)
Afficher tous les articles scientifiques apparentés

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. It is also referred to as a cycloaddition.

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

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