95418-58-9 Usage
Description
4-tert-butoxystyrene is a pendant functionalized styrene that structurally, It is similar to PMOS, both carrying an alkoxyl p-substituent, whose electron-donating and resonance effects allow them to be'polymerized by cationic, anionic, and radical mechanisms. It is used to treatment of its polymers with an acid leads to poly(4-vinylphenol), which finds a wide variety of applications to photoresists, epoxy-curing agents, adhesives, etc.).
Uses
4-tert-Butoxystyrene is used in organic synthesis. It is used to synthesize 4'-tert-butoxy-biphenyl-4-carboxylic acid methyl ester.
Synthesis
Preparation of 4-tert-Butoxystyrene (3-tert-Butoxystyrene). To a 2000-mL three-necked round-bottom flask equipped with a dropping funnel, thermometer, reflux condenser, paddle stirrer and nitrogen inlet were placed 19.4 g (0.80 mol) of magnesium turnings and enough freshly dried and distilled tetrahydrofuran (THF) to cover the turnings. There were then added dropwise with stirring a solution of 143.3g (0.78 mol) of freshly distilled 4-bromostyrene (bp 46-47°C (0.03 mm)) in 500mL of THF. After 20mL of the 4-bromostyrene had been added, an exothermic reaction set in and was maintained between 25 and 35°C by adjusting the rate of addition of the bromo compound and with the aid of an ice bath. After the addition had been completed, the reaction mixture was heated to 60°C for 0.5h. Using a NaC1-ice bath, the mixture was cooled to 0°C and a solution of 100.88g (0.52 mol) of tert-butyl peroxybenzoate in 200 mL of THF was added via the dropping funnel at such a rate that the reaction temperature was maintained between 0 and 5°C. After completion of the addition, the reaction mixture was stirred at 25°C for 2 h. The organic layer was separated from the solid magnesium benzoate by decantation and the volume of the solution reduced on a rotary evaporator. The yellow oil that remained was washed with 1000 mL of 3% aqueous HCl solution and the organic layer separated. The aqueous layer was washed with two 200-mL portions of ether, and the ether and organic layers were combined and together washed with two 75-mL portions of a 10% NaOH solution followed by washing with water until the aqueous washings were neutral. After the solution was dried over Na2S04 and the ether was removed via a rotary evaporator, the remaining pale yellow oil was purified by fractional distillation in the presence of a few milligrams of ionol (2,6-ditert-butyl-4-methylphenol) as an inhibitor. There were obtained 46 g (50% yield, bp 45°C (0.02 mm)) of 4-tert-Butoxystyrene having the following elemental analysis.
References
Living cationic sequential block copolymerization of isobutylene with 4-tert-butoxystyrene: synthesis and characterization of poly(p-hydroxystyrene-b-isobutylene-b-p-hydroxystyrene) triblock copolymers. Bouchékif, H.; Som, A.; Sipos, L.; Faust, R.; Journal of Macromolecular Science, Part A: Pure and Applied Chemistry (2007), 44(4), 359-366.
Check Digit Verification of cas no
The CAS Registry Mumber 95418-58-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,5,4,1 and 8 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 95418-58:
(7*9)+(6*5)+(5*4)+(4*1)+(3*8)+(2*5)+(1*8)=159
159 % 10 = 9
So 95418-58-9 is a valid CAS Registry Number.
InChI:InChI=1/C12H16O/c1-5-10-6-8-11(9-7-10)13-12(2,3)4/h5-9H,1H2,2-4H3
95418-58-9Relevant articles and documents
Iron-Catalyzed Direct Julia-Type Olefination of Alcohols
Landge, Vinod G.,Babu, Reshma,Yadav, Vinita,Subaramanian, Murugan,Gupta, Virendrakumar,Balaraman, Ekambaram
, p. 9876 - 9886 (2020/09/03)
Herein, we report an iron-catalyzed, convenient, and expedient strategy for the synthesis of styrene and naphthalene derivatives with the liberation of dihydrogen. The use of a catalyst derived from an earth-abundant metal provides a sustainable strategy to olefins. This method exhibits wide substrate scope (primary and secondary alcohols) functional group tolerance (amino, nitro, halo, alkoxy, thiomethoxy, and S- A nd N-heterocyclic compounds) that can be scaled up. The unprecedented synthesis of 1-methyl naphthalenes proceeds via tandem methenylation/double dehydrogenation. Mechanistic study shows that the cleavage of the C-H bond of alcohol is the rate-determining step.
Light driven decarboxylative cross coupling of acrylic acid and iodobenzene using [Mo132] type keplerate as a catalyst
Das, Santu,Misra, Archismita,Roy, Soumyajit
, p. 77 - 82 (2017/03/29)
Photochemical decarboxylative cross coupling reaction is one of the most significant research areas in industrial chemistry. Many research groups working on the topic use a photoredox catalyst merged with another coordination catalyst. The major problem in this case is the cost of such a cooperative catalyst system. Thus, to reduce the cost of the catalyst, designing a self-sufficient catalyst system is required. In our present work we have synthesized a giant molybdenum based polyoxometalate which acts as a photocatalyst as well as a coordination catalyst. We have shown that acrylic acid gets decarboxylated in the presence of UV light and gets coupled with iodobenzene to form styrene with maximum yield of 62%. The catalyst material is also stable under the reaction conditions and hence it is reusable.
A general solution for unstable boronic acids: Slow-release cross-coupling from air-stable MIDA boronates
Knapp, David M.,Gillis, Eric P.,Burke, Martin D.
supporting information; experimental part, p. 6961 - 6963 (2009/09/30)
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