1-ACETOXY-1,3-BUTADIENE

Synonym(s):1,3-Butadienyl acetate

CAS NO.：1515-76-0
Empirical Formula: C6H8O2
Molecular Weight: 112.13
MDL number: MFCD00008714
EINECS: 216-159-6
SAFETY DATA SHEET (SDS)
Update Date: 2023-04-23 13:52:06

What is 1-ACETOXY-1,3-BUTADIENE?

Chemical properties

clear colorless to slightly yellow viscous liquid

The Uses of 1-ACETOXY-1,3-BUTADIENE

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.

What are the applications of Application

1-Acetoxy-1,3-butadiene, mixture of cis and trans is a Diels-Alder diene

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.]

Properties of 1-ACETOXY-1,3-BUTADIENE

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 for 1-ACETOXY-1,3-BUTADIENE

Signal word	Danger
Pictogram(s)	Flame Flammables GHS02 Skull and Crossbones Acute Toxicity GHS06
GHS Hazard Statements	H226:Flammable liquids H302:Acute toxicity,oral H311:Acute toxicity,dermal H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P233:Keep container tightly closed. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.