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4-Acetoxystyrene

CAS No.
2628-16-2
Chemical Name:
4-Acetoxystyrene
Synonyms
4-VINYLPHENYL ACETATE;4-ETHENYLPHENOL ACETATE;P-ACETOXYSTYRENE;(4-Ethenylphenyl) acetate;Phenol, 4-ethenyl-, acetate;Phenol, 4-ethenyl-,1-acetate;c-908;ACS/ASM;ACETOXYSTYRENE;4-ACETOXYSTYRENE
CBNumber:
CB9777268
Molecular Formula:
C10H10O2
Molecular Weight:
162.19
MDL Number:
MFCD00075734
MOL File:
2628-16-2.mol
MSDS File:
SDS
Last updated:2024-03-14 18:29:10

4-Acetoxystyrene 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.)
Flash point 190 °F
storage temp. 2-8°C
form Liquid
color Clear colorless
BRN 1862793
InChI InChI=1S/C10H10O2/c1-3-9-4-6-10(7-5-9)12-8(2)11/h3-7H,1H2,2H3
InChIKey JAMNSIXSLVPNLC-UHFFFAOYSA-N
SMILES C1(OC(=O)C)=CC=C(C=C)C=C1
CAS DataBase Reference 2628-16-2(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 7S21904AYN
NIST Chemistry Reference Phenol, 4-ethenyl-, acetate(2628-16-2)
EPA Substance Registry System Phenol, 4-ethenyl-, acetate (2628-16-2)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H317-H319
Precautionary statements  P261-P264-P280-P301+P312-P302+P352-P305+P351+P338
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
Toxicity LD50 orl-rat: 1503 mg/kg EPASR* 8EHQ-1190-1082
NFPA 704
2
2 1

4-Acetoxystyrene price More Price(32)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 380547 4-Acetoxystyrene 96%, contains 200-300 ppm monomethyl ether hydroquinone as inhibitor 2628-16-2 25ml $142 2024-03-01 Buy
Sigma-Aldrich 380547 4-Acetoxystyrene 96%, contains 200-300 ppm monomethyl ether hydroquinone as inhibitor 2628-16-2 5ml $48.7 2023-06-20 Buy
TCI Chemical A1551 4-Vinylphenyl Acetate (stabilized with TBC) >98.0%(GC) 2628-16-2 5g $30 2024-03-01 Buy
TCI Chemical A1551 4-Vinylphenyl Acetate (stabilized with TBC) >98.0%(GC) 2628-16-2 25g $112 2024-03-01 Buy
Alfa Aesar L11601 4-Acetoxystyrene, 95%, stab. 2628-16-2 2g $20.65 2024-03-01 Buy
Product number Packaging Price Buy
380547 25ml $142 Buy
380547 5ml $48.7 Buy
A1551 5g $30 Buy
A1551 25g $112 Buy
L11601 2g $20.65 Buy

4-Acetoxystyrene Chemical Properties,Uses,Production

Description

4-Acetoxystyrene can be used to synthesize Poly(p-hydroxystyrene) as the main component of photoresist. The chemically amplified photoresist of the poly(p-hydroxystyrene) series is currently the mainstream photoresist product in the world, and it is one of the key technologies for processing photo-etched integrated circuits and manufacturing chips.

Chemical Properties

4-Acetoxystyrene is a clear and colorless liquid that is essentially 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.

Uses

4-Acetoxystyrene is a stable Styrene monomer which can be readily polymerized and copolymerized to low, medium and high molecular weight polymers. Undergoes free radical polymerization, similar to styrene.

Application

4-Acetoxystyrene is a polymer that can be used in microlithography and is the precursor of easily derivatized p-hydroxystyrene.

Preparation

The 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%).

2628-16-2.png

Hazard

4-Acetoxystyrene is a flammable liquid and can cause skin and eye irritation upon contact.

Flammability and Explosibility

Not classified

Safety Profile

Moderately toxic by ingestion.Slightly toxic by skin contact. An eye irritant. A combustibleliquid. When heated to decomposition it emits acrid smokeand irritating vapors.

storage

4-Acetoxystyrene should be handled with proper safety precautions and stored in a cool, dry place away from sources of ignition.

Advantages

Grafting 4-Acetoxystyrene (AOS) onto Polypropylene (PP) could significantly improved PP's space charge distribution, DC resistivity, and DC breakdown strength. These improvements were related to carbonyl (polar group) and benzene ring derived from AOS. As the carbonyl in AOS is introduced onto the PP chains by the grafting reaction, the homo-charge injected from the electrodes during the voltage application is trapped by the carbonyl and neutralizes the hetero-charge, decreasing hetero-charge. With the increase of grafting degree, the concentration of carbonyl increases, the corresponding charge trapping ability rises, and thus the extent of neutralizing the hetero-charge increases. The space charge is effectively suppressed. Grafting AOS onto PP significantly increases breakdown performance since AOS possesses chemical construction similar to the benzil-type voltage stabilizer. Because of delocalized π-electrons, AOS possesses a low ionizing potential and high electron affinity, making it capable of capturing the energetic electrons by collision and dissipating the energy, and the breakdown strength is improved. On the other hand, the energy of hot electrons is consumed through Fries rearrangement of AOS, weakening the attack of hot electrons on molecular chains and resulting in enhanced breakdown strength[1].

References

[1] Yue Liang. “Preparation and electrical properties of 4-acetoxystyrene grafted polypropylene for HVDC cable insulation.” Journal of Materials Science: Materials in Electronics 31 5 (2020): 3890–3898.

108-24-7
2628-16-2
Synthesis of 4-Acetoxystyrene from Acetic anhydride
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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) 1-Acetoxy-4-vinylbenzene 4-Vinylphenol acetate Acetic acid p-vinylphenyl ester Styrene-4-ol acetate (4-ethenylphenyl) ethanoate 4-Acetoxystyrene, stabilized with 200-300 ppm MEHQ, 96% 4-Acetoxystyrene Acetic Acid 4-Vinylphenyl Ester 4-Acetoxystyrene,96%,stabilized with 200-300ppm MEHQ 4-Acetoxystyrene 96%, contains 200-300 ppm monomethyl ether hydroquinone as inhibitor 4-Acetoxystyrene, Stabilized with 200 to 300 ppm MEHQ 4-Acetoxystyrene, stabilized 4-ethenyl-phenoacetate c-908 p-vinyl-phenoacetate p-vinylphenolacetate ACETIC ACID 4-VINYLPHENYL ESTER 4-ACETOXYSTYRENE 4-ACETOXYSTYRENE MONOMER 4-ETHENYLPHENOL ACETATE MONOMER 4-Ethenylphenol acetate~4-Vinylphenyl acetate p-Acetoxy Styrene (p-Vinyl Phenyl Acetate) ACETOXYSTYRENE 4-Acetoxystyrene, 98%, stabilized with MEHQ 4-ACETOXYSTYRENE - STABILIZED WITH MEHQ 4-ACETOXYSTYRENE - STABILIZED WITH TBC 4-Acetoxystyrene, 98%, stabilized with TBC para-acetoxystyrene p-Acetoxystyrene 2628-16-2 4-Acetoxystyrene 4-Ethenylphenol acetate 2628-16-2 4-Ethenylphenol acetate 2628-16-2 p-Acetoxystyrene 2628-16-2 4-Acetoxystyrene 4-Acetoxystyrene 2628-16-2 p-Acetoxystyrene 4-Ethenylphenol acetate 2628-16-2 4-Ethenylphenol acetate COA 4-Ethenylphenol acetatephenoacetate 4-Vinylphenyl Acetate (stabilized with TBC)> 4-acetyloxyphenylene 4-ACETOXYSTYRENE 4-ACETOXYSTYRENE MONOMER 4-ETHENYLPHENOL ACETATE 4-ETHENYLPHENOL ACETATE MONOMER 4-VINYLPHENYL ACETATE ACETIC ACID 4-VINYLPHENYL ESTER P-ACETOXYSTYRENE 4-ethenyl-phenoacetate c-908 p-vinyl-phenoacetate p-vinylphenolacetate 4-Ethenylphenol acetate~4-Vinylphenyl acetate p-Acetoxy Styrene (p-Vinyl Phenyl Acetate) Phenol, 4-ethenyl-, acetate ACETOXYSTYRENE 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-ethenyl-phenoacetate (PACS) (4-Ethenylphenyl) acetate Phenol, 4-ethenyl-,1-acetate P-ACETOXYSTYRENE 4-ETHENYLPHENOL ACETATE 4-VINYLPHENYL ACETATE Phenol, 4-ethenyl-, acetate 4-Acetoxy-1-ethenylbenzene ACS/ASM 2628-16-2 CH3CO2C6H4CHCH2 Styrenes 2628-16-2