1-Acetoxy-1,3-butadiene
ALDRICH/220868 - mixture of cis and trans
Synonym: 1,3-Butadienyl acetate
CAS Number: 1515-76-0
Empirical Formula (Hill Notation): C6H8O2
Molecular Weight: 112.13
MDL Number: MFCD00008714
Linear Formula: CH2=CHCH=CHOCOCH3
Product Type: Chemical
| bp | 60-61 °C/40 mmHg (lit.) |
| contains | 0.1% p-tert-butylcatechol as stabilizer |
| density | 0.945 g/mL at 25 °C (lit.) |
| form | liquid |
| functional group | ester |
| InChI | 1S/C6H8O2/c1-3-4-5-8-6(2) |
| InChI key | NMQQBXHZBNUXGJ-SNAWJCMRSA |
| Quality Level | 100  |
| refractive index | n |
| SMILES string | CC(=O)OC=CC=C |
| storage temp. | 2-8°C |
| vapor pressure | 40 mmHg ( 60 °C) |
| 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-cyclohexeneca 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. |
| 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-be |
| Packaging: | 10 g in glass bottle |
| Symbol |   GHS02,GHS06 |
| Signal word | Danger |
| Hazard statements | H226 - H302 - H311 - H315 - H319 - H335 |
| Precautionary statements | P210 - P233 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338 |
| Hazard Codes | Xn |
| Risk Statements | 10-21/22-36/37/38 |
| Safety Statements | 26-36/37 |
| RIDADR | UN 1992 6.1(3) / PGIII |
| WGK Germany | WGK 3 |
| Flash Point(F) | 91.4 °F - closed cup |
| Flash Point(C) | 33 °C - closed cup |
| bp | 60-61 °C/40 mmHg (lit.) |
| Density | 0.945 g/mL at 25 °C (lit.) |
| Refractive Index | n |
| Storage Temp. | 2-8°C |
| UNSPSC | 12352100 |