4-Ethenylphenyl acetate
4-VINYLPHENYL ACETATE · 4-ETHENYLPHENOL ACETATE · ACETOXYSTYRENE · P-ACETOXYSTYRENE · VPAC · (4-Ethenylphenyl) acetate · Phenol, 4-ethenyl-, acetate · Phenol, 4-ethenyl-,1-acetate
Identifiers & Physical Properties
| CAS No. | 2628-16-2 |
|---|---|
| Molecular formula | C10H10O2 |
| Average molar mass | 162.18 g/mol |
| Monoisotopic mass | 162.06807956 g/mol |
| SMILES | C=Cc1ccc(OC(C)=O)cc1 |
| InChIKey | JAMNSIXSLVPNLC-UHFFFAOYSA-N |
| PubChem CID | 75821 |
| ChEMBL | CHEMBL3186305 |
| EC No. | 434-600-2 |
| DTXSID | DTXSID2044898 |
Chemical & Physical Properties
| XLogP | 2.5 |
|---|---|
| Topological polar surface area | 26.3 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 3 |
| Heavy atoms | 12 |
| Formal charge | 0 |
| Complexity | 167 |
| Physical Description | Liquid |
| 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 conditions | 2-8°C |
| Physical state | Liquid |
| Color | Clear colorless |
| Viscosity | 4.2cP(25°CBrookfield)(lit.) |
| 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) |
| UNSPSC Code | 12162002 |
| NACRES | NA.23 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302-H315-H317-H319 |
| GHS precautionary statements | P261-P264-P280-P301+P312-P302+P352-P305+P351+P338 |
| Hazard symbols | Xn |
| Risk statements (R) | 22-38-43-36/38 |
| Safety statements (S) | 36/37-26 |
| UN transport number | 2810 |
| Water hazard class (WGK) | 3 |
| RTECS number | SL3784000 |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2Skin Sens. 1 |
| Packing group | III |
| Customs code | 29153900 |
| Storage class | 10 - Combustible liquids |
| Toxicity | LD50 orl-rat: 1503 mg/kg EPASR* 8EHQ-1190-1082 |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | DangerH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 171 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Phenol, 4-ethenyl-, 1-acetate is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 4-ethenyl-, 1-acetate are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.Status: Active Update: 16-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/24914Phenol, 4-ethenyl-, acetate: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | SL3784000 |
| UN transport number | 2810 |
| Customs code | 29153900 |
| Toxicity | LD50 orl-rat: 1503 mg/kg EPASR* 8EHQ-1190-1082 |
| Risk statements (R) | 22-38-43-36/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn |
| Safety statements (S) | 36/37-26 |
| Hazard class | 6.1Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2Skin Sens. 1 |
| Storage class | 10 - Combustible liquids |
| Packing group | III |
| GHS hazard statements | H302-H315-H317-H319 |
| REACH registrations | Active |
| GHS precautionary statements | P261-P264-P280-P301+P312-P302+P352-P305+P351+P338 |
Applications & Uses
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.
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.
Preparation & Synthesis
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%).