1-ACETOXY-1,3-BUTADIENE
- Product Name
- 1-ACETOXY-1,3-BUTADIENE
- CAS No.
- 1515-76-0
- Chemical Name
- 1-ACETOXY-1,3-BUTADIENE
- Synonyms
- 1-Acetoxybutadiene;Butadienyl acetate;1,3-BUTADIENYL ACETATE;1-ACETOXY-1,3-BUTADIENE;1,3-butadien-1-ol,acetate;1,3-BUTADIEN-1-YL ACETATE;Acetic acid-1,3-butadienyl;(E)-1,3-Butadienyl acetate;Buta-1,3-dien-1-yl acetate;(1E)-1,3-Butadienyl acetate
- CBNumber
- CB6244909
- Molecular Formula
- C6H8O2
- Formula Weight
- 112.13
- MOL File
- 1515-76-0.mol
1-ACETOXY-1,3-BUTADIENE Property
- 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
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H226Flammable liquid and vapour
H302Harmful if swallowed
H311Toxic in contact with skin
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233Keep container tightly closed.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 220868
- Product name
- 1-Acetoxy-1,3-butadiene
- Purity
- mixture of cis and trans
- Packaging
- 10g
- Price
- $308
- Updated
- 2024/03/01
- Product number
- 408671
- Product name
- 1-Acetoxy-1,3-butadiene
- Packaging
- 500mg
- Price
- $355
- Updated
- 2021/12/16
- Product number
- A164285
- Product name
- 1-Acetoxy-1,3-butadiene
- Packaging
- 1g
- Price
- $120
- Updated
- 2021/12/16
- Product number
- CHM0006438
- Product name
- 1-ACETOXY-1,3-BUTADIENE
- Purity
- 95.00%
- Packaging
- 10G
- Price
- $1232.15
- Updated
- 2021/12/16
1-ACETOXY-1,3-BUTADIENE Chemical Properties,Usage,Production
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.]