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| | 1-ACETOXY-1,3-BUTADIENE Basic information |
| Product Name: | 1-ACETOXY-1,3-BUTADIENE | | Synonyms: | (1E)-1,3-Butadienyl acetate;1,3-butadien-1-ol,acetate;1,3-Butadienylester kyseliny octove;1,3-butadienylesterkyselinyoctove;1-acetoxy-1,3-butadiene,mixtureofisomers;1-Acetoxybutadiene;Acetic acid, 1,3-butadienyl ester;aceticacid,1,3-butadienylester | | CAS: | 1515-76-0 | | MF: | C6H8O2 | | MW: | 112.13 | | EINECS: | 216-159-6 | | Product Categories: | | | Mol File: | 1515-76-0.mol |  |
| | 1-ACETOXY-1,3-BUTADIENE Chemical Properties |
| Boiling point | 60-61 °C40 mm Hg(lit.) | | density | 0.96 g/mL at 20 °C(lit.) | | vapor pressure | 40 mm Hg ( 60 °C) | | refractive index | n20/D 1.47 | | Fp | 92 °F | | storage temp. | 2-8°C | | form | Liquid | | BRN | 1743394 | | CAS DataBase Reference | 1515-76-0(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 10-21/22-36/37/38 | | Safety Statements | 26-36/37 | | RIDADR | UN 1992 3/PG 3 | | WGK Germany | 3 | | RTECS | EJ1225000 | | HazardClass | 3 | | PackingGroup | III | | HS Code | 2915390090 | | Toxicity | skn-rbt 100 mg/24H open AIHAAP 23,95,62 |
| | 1-ACETOXY-1,3-BUTADIENE Usage And Synthesis |
| Chemical Properties | clear colorless to slightly yellow viscous liquid | | Uses | 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. | | 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: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 Preparation Products And Raw materials |
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