ChemicalBook CAS DataBase List 1515-76-0

1515-76-0

Name	1-ACETOXY-1,3-BUTADIENE
CAS	1515-76-0
EINECS(EC#)	216-159-6
Molecular Formula	C6H8O2
MDL Number	MFCD00008714
Molecular Weight	112.13
MOL File	1515-76-0.mol

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

Chemical Properties

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

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 . less more
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 . less more
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 less more

Hazard Information

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.]

Spectrum Detail

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