220868

1-Acetoxy-1,3-butadiene

mixture of cis and trans

• Synonym(s): 1,3-Butadienyl acetate
• Linear Formula: CH₂=CHCH=CHOCOCH₃
• CAS Number: 1515-76-0
• Molecular Weight: 112.13
• Beilstein/REAXYS Number: 1743394
• MDL number: MFCD00008714
• UNSPSC Code: 12352100
• PubChem Substance ID: 24853196
• NACRES: NA.22

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS02,GHS06
• signalword: Danger
• hcodes: H226,H302,H311,H315,H319,H335
• pcodes: P210 - P233 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338
• 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