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

Flash point:

92 °F

storage temp. 

2-8°C

form 

Liquid

BRN 

1743394

CAS DataBase Reference

1515-76-0(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

Toxicity

skn-rbt 100 mg/24H open AIHAAP 23,95,62

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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(1515-76-0)Related Product Information

• Crotonaldehyde
• 1,3-Butadiene
• 19-Nor-17-alpha-pregna-3,5-dien-20-yne-3,17-diol, diacetate
• 1-ACETOXY-1,3-BUTADIENE
• TRANS,TRANS-1,4-DIACETOXY-1,3-BUTADIENE
• 4-tert-Butylcatechol
• 3-(METHOXYCARBONYL)-2H-CYCLOHEPTA[B]FURAN-2-ONE
• 5-ISOPROPYL-3-(METHOXYCARBONYL)-2H-CYCLOHEPTA[B]FURAN-2-ONE
• 3-ACETYL CYCLOHEPTA[B]FURAN-2-ONE
• 3-ACETOXY-2(1H)-PYRIDONE 97
• 2-ACETOXY-1,3-BUTADIENE
• 3,5-CHOLESTADIEN-3-OL 3-ACETATE
• 2,4,6-CYCLOHEPTATRIEN-1-ONE, 2-HYDROXY-3-IODO-, p-NITROBENZOATE
• 2H-CYCLOHEPTA(B)FURAN-2-ONE
• 3,5-ESTRADIEN-3,17-BETA-DIOL DIACETATE
• TESTOSTERONE ENOL DIACETATE
• AKOS 212-65
• AKOS 210-09