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Sigma-Aldrich

1-Acetoxy-1,3-butadiene

mixture of cis and trans

Synonym(s):

1,3-Butadienyl acetate

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About This Item

Linear Formula:
CH2=CHCH=CHOCOCH3
CAS Number:
1515-76-0
Molecular Weight:
112.13
Beilstein:
1743394
MDL number:
MFCD00008714
UNSPSC Code:
12352100
PubChem Substance ID:
24853196
NACRES:
NA.22

vapor pressure

40 mmHg ( 60 °C)

form

liquid

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

SMILES string

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

InChI

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

InChI key

NMQQBXHZBNUXGJ-SNAWJCMRSA-N

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.

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.

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

91.4 °F - closed cup

Flash Point(C)

33 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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The Journal of Organic Chemistry, 58, 7146-7146 (1993)
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
Gas phase acetoxylation of 1, 3-butadiene over palladium catalysts Part 1: the catalytic activity and structure of Pd-Sb-KOAc catalysts.
Shinohara H.
Applied Catalysis, 10(1), 27-42 (1984)
Structure determination of the Diels-Alder product of a ketovinylphosphonate with< i> E</i>-1-acetoxy-1, 3-butadiene.
McClure CK, et al.
Tetrahedron Letters, 37(13), 2153-2156 (1996)
Intra- and Intermolecular Oxa-Pictet-Spengler Cyclization Strategy for the Enantioselective Synthesis of Deoxy Analogues of (+)-Nanomycin A Methyl Ester, (+)-Eleutherin, (+)-Allo-Eleutherin, and (+)-Thysanone
R. T. Sawant, et al.
European Journal of Organic Chemistry, 23, 4442-4449 (2010)
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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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