| Identification | More | [Name]
4-tert-Butoxystyrene | [CAS]
95418-58-9 | [Synonyms]
4-TERT-BUTOXYSTYRENE
P-T-BUTOXYSTYRENE
p-tert-butoxystyrene
4-T-BUTOXYSTYRENE
butoxy styrene
4-tert-butoxystyene
(1-Butoxyethenyl)benzene
(1-Butoxyvinyl)benzene
Butyl 1-phenylethenyl ether
1-Vinyl-4-(tert-butyloxy)benzene
4-(tert-Butyloxy)styrene
4-tert-Butyloxystyrene
p-(tert-Butyloxy)styrene
tert-Butyl(4-vinylphenyl) ether
T-BUTYL=P-VINYLPHENYL=ETHER | [EINECS(EC#)]
619-127-3 | [Molecular Formula]
C12H16O | [MDL Number]
MFCD00145183 | [Molecular Weight]
176.25 | [MOL File]
95418-58-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
−38 °C(lit.)
| [Boiling point ]
72-73 °C0.1 mm Hg(lit.)
| [density ]
0.936 g/mL at 25 °C(lit.)
| [vapor pressure ]
17.999Pa at 20℃ | [refractive index ]
n20/D 1.524(lit.)
| [Fp ]
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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3 | [HS Code ]
2902900000 |
| Hazard Information | Back Directory | [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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