Benzene, 1-ethenyl-2-(1-Methylethoxy)-

Benzene, 1-ethenyl-2-(1-Methylethoxy)- Property

Boiling point:

231.2±9.0 °C(Predicted)

Density 

0.938±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C11H14O/c1-4-10-7-5-6-8-11(10)12-9(2)3/h4-9H,1H2,2-3H3

InChIKey

SXCKVSZTZAMSRS-UHFFFAOYSA-N

SMILES

C1(C=C)=CC=CC=C1OC(C)C

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Benzene, 1-ethenyl-2-(1-Methylethoxy)- Chemical Properties,Usage,Production

Uses

2-Isopropoxystyrene is an organic intermediate that can be prepared by first preparing O-(2-propoxy)salicylaldehyde from salicylaldehyde, and then preparing 2-isopropoxystyrene through the Wittig reaction.

Synthesis

1-Isopropoxy-2-vinylbenzene was synthesized as follows: first, 15.65 g of methyltriphenylphosphonium bromide was suspended in 100 mL of dry tetrahydrofuran (THF), and 19.0 mL of n-butyllithium (n-BuLi, 2.5 M n-hexane solution) was slowly added to this suspension at room temperature. The reaction mixture was then transformed into an orange colored solution with continuous stirring for 4 hours. Subsequently, 6.00 g (36.5 mmol) of 2-isopropoxybenzaldehyde dissolved in 25 mL of anhydrous THF was slowly added dropwise under stirring. Upon completion of the dropwise addition, the formation of a white precipitate was observed in the reaction system. After continued stirring of the reaction mixture for 1 h, vacuum concentration was carried out to give a viscous yellow oil. The crude product was purified by a short silica gel column (eluent: heptane) followed by vacuum distillation to give 3.66 g of 1-isopropoxy-2-vinylbenzene as a colorless liquid. The structure of the product was confirmed by 1H-NMR (300 MHz, CDCl3) and GC-MS analysis: 1H-NMR (300 MHz, CDCl3) δ 1.27 (d, J = 6.1 Hz, 6H), 4.47 (m, 1H), 5.15 (dd, J1 = 11.2 Hz, J2 = 1.6 Hz, 1H), 5.65 (dd, J1 = 17.8 Hz, J2 = 1.6 Hz, 1H), 6.78-6.88 (m, 2H), 6.92-7.05 (m, 1H), 7.08-7.16 (m, 1H), 7.40 (dd, J1 = 7.6 Hz, J2 = 1.7 Hz, 1H); GC-MS showed purity of >99.0%, MS (EI): 162.

References

[1] Organometallics, 2018, vol. 37, # 14, p. 2212 - 2216
[2] Chemistry - A European Journal, 2004, vol. 10, # 3, p. 777 - 784
[3] Patent: WO2015/155593, 2015, A1. Location in patent: Page/Page column 50