1-ACETOXY-1,3-BUTADIENE
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1-ACETOXY-1,3-BUTADIENE ??
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- 60-61 °C40 mm Hg(lit.)
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- 0.96 g/mL at 20 °C(lit.)
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- 40 mm Hg ( 60 °C)
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- n
20/D 1.47
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- 92 °F
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- 2-8°C
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- BRN
- 1743394
- CAS ??????
- 1515-76-0(CAS DataBase Reference)
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- ?? ? ???? ?? (GHS)
| ??? ?? | Xn | ||
|---|---|---|---|
| ?? ???? ?? | 10-21/22-36/37/38 | ||
| ????? | 26-36/37 | ||
| ????(UN No.) | UN 1992 3/PG 3 | ||
| WGK ?? | 3 | ||
| RTECS ?? | EJ1225000 | ||
| ?? ?? | 3 | ||
| ???? | III | ||
| HS ?? | 2915390090 | ||
| ?? | skn-rbt 100 mg/24H open AIHAAP 23,95,62 | ||
| ???? ?? | KE-03744 |
| ????(GHS): |
 
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1-ACETOXY-1,3-BUTADIENE C??? ??, ??, ??
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clear colorless to slightly yellow viscous liquid??
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.
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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:4?) has been reported.Safety Profile
Poison by inhalation. Moderatelytoxic by other routes. A skin irritant. Mutation datareported. When heated to decomposition it emits acridsmoke.Purification Methods
The commercial sample is stabilised with 0.1% of p-tert-butylcatechol. If the material contains crotonaldehyde (by IR, used in its synthesis), it should be dissolved in Et2O, shaken with 40% aqueous sodium bisulfite, then 5% aqueous Na2CO3, water, dried (Na2SO4) and distilled several times in a vacuum through a Widmer [Helv Chim Acta 7 59 1924] (p 11) or Vigreux column (p 11) [Wicterle & Hudlicky Collect Czech Chem Commun 12 564 1947, Hagemeyer & Hull Ind Eng Chem 41 2920 1949]. [Beilstein 2 III 295.]1-ACETOXY-1,3-BUTADIENE ?? ?? ? ???
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1-ACETOXY-1,3-BUTADIENE ?? ??
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| ??? | ?? | ??? | ?? | ?? ? | ?? |
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1-ACETOXY-1,3-BUTADIENE ?? ??:
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