4-Acetoxystyrene

4-Acetoxystyrene
  • CAS No.:2628-16-2
Other grades of this product :
4-Acetoxystyrene Basic information
Product Name:4-Acetoxystyrene
Synonyms:ACETIC ACID 4-VINYLPHENYL ESTER, (STABILIZED WITH PHENOTHIAZINE);4-ACETOXYSTYRENE / 4-VINYLPHENYL ACETATE;4-ACETOXYSTYRENE, 95%, STAB. WITH 15-25PPM PHENOTHIAZINE;4-Acetoxystyrene, 95%, stab.;4-Vinylphenyl Acetate (stabilized with TBC);(4-Ethenylphenyl) acetate;1-Acetoxy-4-vinylbenzene;4-Vinylphenol acetate
CAS:2628-16-2
MF:C10H10O2
MW:162.19
EINECS:434-600-2
Product Categories:Styrenes
Mol File:2628-16-2.mol
4-Acetoxystyrene Chemical Properties
Melting point 7-8 °C (lit.)
Boiling point 260 °C (lit.)
density 1.06 g/mL at 25 °C (lit.)
refractive index n20/D 1.538(lit.)
Fp 190 °F
storage temp. 2-8°C
form Liquid
color Clear colorless
BRN 1862793
InChIKeyJAMNSIXSLVPNLC-UHFFFAOYSA-N
CAS DataBase Reference2628-16-2(CAS DataBase Reference)
NIST Chemistry ReferencePhenol, 4-ethenyl-, acetate(2628-16-2)
EPA Substance Registry SystemPhenol, 4-ethenyl-, acetate (2628-16-2)
Safety Information
Hazard Codes Xn
Risk Statements 22-38-43-36/38
Safety Statements 36/37-26
RIDADR 2810
WGK Germany 3
RTECS SL3784000
TSCA Yes
HazardClass 6.1
PackingGroup III
HS Code 29153900
ToxicityLD50 orl-rat: 1503 mg/kg EPASR* 8EHQ-1190-1082
MSDS Information
ProviderLanguage
4-Ethenylphenol acetate English
SigmaAldrich English
ALFA English
4-Acetoxystyrene Usage And Synthesis
Chemical Properties4-Acetoxystyrene is a clear colorless liquid, the acetic acid ester of p-vinylphenol. It will homopolymerize readily in the same manner that styrene homopolymerizes and can also be copolymerized with styrene and with monomers which are copolymerizable with styrene. 4-Acetoxystyrene is homopolymerized and copolymerized in aqueous emulsion and, without isolation, the polymer is hydrolyzed to homopolymers and copolymers of p-vinylphenol with a base. Homopolymers and copolymers of p-vinylphenol are used as epoxy resin curing agents and in the preparation of epoxy resins by reaction with epichlorohydrin.
Uses4-Acetoxystyrene is a stable Styrene monomer which can be readily polymerized and copolymerized to low, medium and high molecular weight polymers. Precursor to p-hydroxystyrene that is readily derivatized. Undergoes free radical polymerization, similar to styrene.
PreparationThe preparation of 4-Acetoxystyrene is as follows:Add p-hydroxystyrene (120g) to a 2L four-neck bottle. triethylamine(106g), phenothiazine (1.2g), Methyl tert-butyl ether (480 g), Dry ice-ethanol bath to -5 to 0 °C, acetyl chloride (86g) was added dropwise with stirring. The internal temperature is controlled at -5 to 0 °C. After the completion of the dropwise addition, the temperature was raised at 10 to 20 °C to continue the reaction for 1 hour. Sampling analysis (central control 1, raw material After completion of the reaction, the mixture was filtered, and the cake was washed with methyl t-butyl ether (50 g × 3). The filtrate was quenched by the addition of 4 g of methanol, and the reaction was stirred for 10 minutes. After completion, phenothiazine (1.2 g) was added and the reaction mixture was concentrated.Methyl tert-butyl ether (580 g) was recovered to give a crude product (160 g).The crude product was distilled under reduced pressure to give the product, p-acetoxy styrene (142 g), yield 87.7%, and sampled for analysis (main content >99%).
Flammability and ExplosibilityNotclassified
Safety ProfileModerately toxic by ingestion.Slightly toxic by skin contact. An eye irritant. A combustibleliquid. When heated to decomposition it emits acrid smokeand irritating vapors.

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