2628-16-2 Usage
Description
4-Ethenylphenol acetate, also known as 4-Acetoxystyrene, is a stable styrene monomer that can be readily polymerized and copolymerized to create polymers with varying molecular weights. It serves as a precursor to p-hydroxystyrene, which is easily derivatized. 4-Ethenylphenol acetate undergoes free radical polymerization, similar to styrene, and is characterized by its clear, colorless liquid appearance.
Uses
Used in Polymer Industry:
4-Ethenylphenol acetate is used as a monomer for the production of low, medium, and high molecular weight polymers. Its ability to homopolymerize and copolymerize with styrene and other compatible monomers makes it a versatile building block for various polymer applications.
Used in Chemical Synthesis:
As a precursor to p-hydroxystyrene, 4-Ethenylphenol acetate is used in the synthesis of various chemical compounds. The p-hydroxystyrene derived from it can be further modified or functionalized to create a range of specialty chemicals.
Used in Epoxy Resin Industry:
4-Ethenylphenol acetate is used as a curing agent for epoxy resins. The homopolymers and copolymers of p-vinylphenol, which are obtained by hydrolyzing the polymers of 4-Acetoxystyrene, are effective curing agents for epoxy resins, enhancing their performance in various applications.
Used in Manufacturing of Epoxy Resins:
In addition to their role as curing agents, homopolymers and copolymers of p-vinylphenol are also used in the preparation of epoxy resins. This is achieved through a reaction with epichlorohydrin, resulting in epoxy resins with specific properties tailored for various industrial applications.
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
Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- And Alkynylnaphthoquinones and Derivatives
Demidoff, Felipe C.,Rodrigues Filho, Eduardo José P.,De Souza, Andréa Luzia F.,Netto, Chaquip D.,De Carvalho, Leandro L.
supporting information, p. 4097 - 4109 (2021/08/31)
Functionalized 1,4-naphthoquinones have been employed as versatile synthons in organic synthesis, in addition to presenting a large array of biological activities. Herein, the applications of 2-amino-/ acetylamino-substituted 3-iodo-1,4-naphthoquinones in cross-coupling reactions are described to successfully afford sixteen novel 3-styryl-1,4-naphthoquinones (amino-stilbene-quinone hybrids) and four 3-alkynyl-1,4-naphthoquinone in overall good yields. Interestingly, the alkynylated derivatives could be obtained from ligand- and Pd-free Cu I -mediated cross-coupling reactions, after extensive investigations to exclude Pd as a co-catalyst. Lastly, the desilanized terminal alkyne was subjected to click chemistry reactions to give two novel triazole-1,4-naphthoquinone hybrids.
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.