| Identification | More | [Name]
1-ACETOXY-1,3-BUTADIENE | [CAS]
1515-76-0 | [Synonyms]
1,3-BUTADIEN-1-YL ACETATE
1,3-BUTADIENYL ACETATE
1-ACETOXY-1,3-BUTADIENE
(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
Butadienyl acetate
1-ACETOXY-1,3-BUTADIENE (CIS+TRANS)
1-ACETOXY-1,3-BUTADIENE, MIXTURE OF CIS AND TRANS
1-Acetoxy-1,3-butadiene, 97% mixture of isomers
crotonaldehyde enol acetate
1-ACETOXY-1,3-BUTADIENE, CIS + TRANS , STABILIZED WITH 0.1% 4-TERT-BUTYLCATECHOL
1-ACETOXY-1,3-BUTADIENE, CIS + TRANS, 90+%, STAB. WITH 0.1%
1-Acetoxy-1,3-butadiene, cis + trans, 90+%, stab. with 0.1% 4-tert-butylcatechol
1-Acetoxy-1,3-butadiene, cis + trans, 95%, stab. with 0.1% 4-tert-butylcatechol | [EINECS(EC#)]
216-159-6 | [Molecular Formula]
C6H8O2 | [MDL Number]
MFCD00008714 | [Molecular Weight]
112.13 | [MOL File]
1515-76-0.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to slightly yellow viscous liquid | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R10:Flammable.
R21/22:Harmful in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
UN 1992 3/PG 3
| [WGK Germany ]
3
| [RTECS ]
EJ1225000
| [HazardClass ]
3 | [PackingGroup ]
III | [Toxicity]
skn-rbt 100 mg/24H open AIHAAP 23,95,62 |
| Hazard Information | Back Directory | [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.] |
|
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Alfa Aesar
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400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
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| Tel: |
021-021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
| Company Name: |
Sigma-Aldrich
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| Tel: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
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