220868

1-Acetoxy-1,3-butadien

mixture of cis and trans

• Synonym(e): 1,3-Butadienyl-acetat
• Lineare Formel: CH₂=CHCH=CHOCOCH₃
• CAS-Nummer: 1515-76-0
• Molekulargewicht: 112.13
• Beilstein: 1743394
• MDL-Nummer: MFCD00008714
• UNSPSC-Code: 12352100
• PubChem Substanz-ID: 24853196
• NACRES: NA.22

Eigenschaften

• Dampfdruck: 40 mmHg ( 60 °C)
• Qualitätsniveau: 100
• Form: liquid
• Enthält: 0.1% p-tert-butylcatechol as stabilizer
• Brechungsindex: n20/D 1.469 (lit.)
• bp: 60-61 °C/40 mmHg (lit.)
• Dichte: 0.945 g/mL at 25 °C (lit.)
• Funktionelle Gruppe: ester
• Lagertemp.: 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+
• InChIKey: NMQQBXHZBNUXGJ-SNAWJCMRSA-N

Beschreibung

Allgemeine Beschreibung

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.

Anwendung

Diels-Alder diene for reaction with dienophiles such as maleimides, a juglone, and a butyne-1,4-dione.

Sicherheitshinweise

• Piktogramme: GHS02,GHS06
• Signalwort: Danger
• H-Sätze: H226,H302,H311,H315,H319,H335
• P-Sätze: P210 - P233 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338
• Gefahreneinstufungen: Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 3 - Flammable liquids
• WGK: WGK 3
• Flammpunkt (°F): 91.4 °F - closed cup
• Flammpunkt (°C): 33 °C - closed cup
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter