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220868

Sigma-Aldrich

1-Acetoxy-1,3-butadiene

mixture of cis and trans

Sinónimos:

1,3-Butadienyl acetate

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About This Item

Fórmula lineal:
CH2=CHCH=CHOCOCH3
Número de CAS:
1515-76-0
Peso molecular:
112.13
Beilstein/REAXYS Number:
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

signalword

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

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

91.4 °F - closed cup

flash_point_c

33 °C - closed cup

ppe

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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.
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Chemical & pharmaceutical bulletin, 52(9), 1114-1116 (2004-09-02)
Oxidation of 2- and 3-hydroxycarbazoles with Frémy's salt gave the corresponding ortho-carbazolequinones. These molecules react as carbodienophiles in Diels-Alder reaction with 1-acetoxy-1,3-butadiene and 1,3-cyclopentadiene to provide the novel benzocarbazolequinone structures 15, 16, 18 and 19.
Structure determination of the Diels-Alder product of a ketovinylphosphonate with< i> E</i>-1-acetoxy-1, 3-butadiene.
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Tetrahedron Letters, 37(13), 2153-2156 (1996)
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Artículos

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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