2628-16-2 Usage
Chemical Properties
4-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.
Uses
4-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.
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%).
Flammability and Explosibility
Notclassified
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.
Check Digit Verification of cas no
The CAS Registry Mumber 2628-16-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,6,2 and 8 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2628-16:
(6*2)+(5*6)+(4*2)+(3*8)+(2*1)+(1*6)=82
82 % 10 = 2
So 2628-16-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H10O2/c1-3-9-4-6-10(7-5-9)12-8(2)11/h3-7H,1H2,2H3
2628-16-2Relevant articles and documents
Synthesis method of p-acetoxystyrene
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Paragraph 0033; 0036; 0037-0044, (2021/04/26)
The invention discloses a synthesis method of p-acetoxystyrene, which relates to the field of organic synthesis. The synthesis route of the synthesis method is as follows: 1, adding p-hydroxyacetophenone and an acetylation reagent into a first solvent, and carrying out esterification reaction under an alkaline condition to generate p-acetoxyacetophenone, 2, adding p-acetoxyacetophenone into a second solvent, and reducing the p-acetoxyacetophenone into 4-acetoxyphenyl methyl methanol under the catalysis of a catalyst in a hydrogen atmosphere, and 3, dehydrating the 4-acetoxyphenyl methyl methanol in an alkaline ionic liquid to obtain the p-acetoxystyrene. The method is high in yield, low in three wastes, green and clean, and the recovery cost and the equipment cost are reduced.
Electrochemical fluorosulfonylation of styrenes
Jiang, Yi-Min,Wu, Shao-Fen,Yan, Hong,Ye, Ke-Yin,Yu, Yi,Yuan, Yaofeng
supporting information, p. 11481 - 11484 (2021/11/16)
An environmentally friendly and efficient electrochemical fluorosulfonylation of styrenes has been developed. With the use of sulfonylhydrazides and triethylamine trihydrofluoride, a diverse array of β-fluorosulfones could be readily obtained. This reaction features mild conditions and a broad substrate scope, which could also be conveniently extended to a gram-scale preparation.
The photoredox-catalyzed hydrosulfamoylation of styrenes and its application in the novel synthesis of naratriptan
Chen, Miaomiao,Ding, Xin,Gao, Yongyue,He, Xingxing,Kang, Jin,Lu, Aidang,Wang, Qingmin,Wang, Ziwen,Zhang, Mingjun
supporting information, p. 9140 - 9143 (2021/09/14)
The hydrosulfamoylation of diverse aryl olefins provides facile access to alkylsulfonamides. Here we report a novel protocol utilizing radical-mediated addition and a thiol-assisted strategy to achieve the hydrosulfamoylation of diverse styrenes in modest to excellent yields under mild and economic reaction conditions. The methodology was found to provide an efficient and convenient approach for the synthesis of the anti-migraine drug naratriptan and it also can be used for the late-stage functionalization of natural products or medicines.
