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Merck
CN

220868

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24853196
MDL number:
MFCD00008714
Beilstein/REAXYS Number:
1743394
Form:
liquid

Key Documents

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InChI

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

SMILES string

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

InChI key

NMQQBXHZBNUXGJ-SNAWJCMRSA-N

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.)

functional group

ester

storage temp.

2-8°C

Quality Level

100

Related Categories

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

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCM6228
MKCC6633
MKBX1238V
MKBP3083V
54297LJV

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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)
Muriel Compain-Batissou et al.
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.
Enantio-face control by molecular sieves in the asymmetric Diels-Alder reaction
Moharram SM, et al.
Tetrahedron Letters, 41(34), 6669-6673 (2000)
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)
Journal of the Chemical Society. Perkin Transactions 1, 1925-1925 (1993)
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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.

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