1-ACETOXY-1,3-BUTADIENE

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 Structure
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 Reference1515-76-0(CAS DataBase Reference)
Safety Information
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
Toxicityskn-rbt 100 mg/24H open AIHAAP 23,95,62
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
1-ACETOXY-1,3-BUTADIENE Usage And Synthesis
Chemical Propertiesclear colorless to slightly yellow viscous liquid
Uses1-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 Description1-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 ProfilePoison by inhalation. Moderatelytoxic by other routes. A skin irritant. Mutation datareported. When heated to decomposition it emits acridsmoke.
Purification MethodsThe 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
Preparation Products2-Chloro-1,4-naphthoquinone-->3-Cyclohexene-1-carboxylic acid, 2-(acetyloxy)-, ethyl ester
3,5-CHOLESTADIEN-3-OL 3-ACETATE TRANS,TRANS-1,4-DIACETOXY-1,3-BUTADIENE 2,4,6-CYCLOHEPTATRIEN-1-ONE, 2-HYDROXY-3-IODO-, p-NITROBENZOATE 3,5-ESTRADIEN-3,17-BETA-DIOL DIACETATE AURORA KA-5493 3-ACETOXY-2(1H)-PYRIDONE 97 1,3-Butadiene AKOS 212-65 2-ACETOXY-1,3-BUTADIENE AKOS 214-09 2H-CYCLOHEPTA(B)FURAN-2-ONE 1-ACETOXY-1,3-BUTADIENE 3-ACETYL CYCLOHEPTA[B]FURAN-2-ONE TESTOSTERONE ENOL DIACETATE AKOS 210-09 19-Nor-17-alpha-pregna-3,5-dien-20-yne-3,17-diol, diacetate 3-(METHOXYCARBONYL)-2H-CYCLOHEPTA[B]FURAN-2-ONE 5-ISOPROPYL-3-(METHOXYCARBONYL)-2H-CYCLOHEPTA[B]FURAN-2-ONE

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