4-tert-Butoxystyrene Chemical Properties

Melting point:

−38 °C(lit.)

Boiling point:

256.8±9.0 °C Press: 760 Torr

Density 

0.936 g/mL at 25 °C(lit.)

vapor pressure 

17.999Pa at 20℃

refractive index 

n20/D 1.524(lit.)

Flash point:

207 °F

InChI

InChI=1S/C12H16O/c1-5-10-6-8-11(9-7-10)13-12(2,3)4/h5-9H,1H2,2-4H3

InChIKey

GRFNSWBVXHLTCI-UHFFFAOYSA-N

SMILES

C1(OC(C)(C)C)=CC=C(C=C)C=C1

LogP

3.83 at 22℃ and pH7

CAS DataBase Reference

95418-58-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2902900000

MSDS

• Language:English Provider:SigmaAldrich

4-tert-Butoxystyrene Usage And Synthesis

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.).

Chemical Properties

Colorless to Almost colorless clear liquid.

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.

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