(4-Vinylphenyl)methanol Chemical Properties

Boiling point:

132-137 °C(Press: 15 Torr)

Density 

1.038±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Acetonitrile (Slightly), Chloroform (Slightly)

pka

14.38±0.10(Predicted)

form 

Oil

color 

Colourless

InChI

InChI=1S/C9H10O/c1-2-8-3-5-9(7-10)6-4-8/h2-6,10H,1,7H2

InChIKey

CLECMSNCZUMKLM-UHFFFAOYSA-N

SMILES

C1(CO)=CC=C(C=C)C=C1

(4-Vinylphenyl)methanol Usage And Synthesis

Uses

(4-Vinylphenyl)methanol is a chlorine-containing organic compound that is used as an intermediate in the production of other chemicals. It is also used as a solvent, plasticizer, and stabilizer.

Synthesis

The general procedure for the synthesis of (4-vinylphenyl)methanol from 4-vinylbenzoic acid was as follows: 4-vinylbenzoic acid (500 mg, 3.37 mmol) was dissolved in Et2O (25 mL) according to the methodology described in the literature [31] and slowly added dropwise to a 0 °C LiAlH4 (758 mg, 19.97 mmol) in THF (80 mL) suspension. The reaction mixture was gradually warmed to room temperature and stirred continuously for 1 hour. Upon completion of the reaction, water (256 μL), 10 wt% NaOH solution (512 μL) and water (768 μL) were added slowly and sequentially to quench the reaction. The mixture was vigorously stirred until a white solid was formed. The crude reaction mixture was filtered and the supernatant was dried with anhydrous Na2SO4 and concentrated under reduced pressure. The resulting oil was purified by silica gel column chromatography with hexane:EtOAc (4:1) as eluent to afford the target product (4-vinylphenyl)methanol (280 mg, 62%) as a colorless oil. The physical and spectral data of the product were in agreement with those reported in the literature [31].1H NMR (CDCl3, 500 MHz) δ: 4.66 (s, 2H), 5.24 (d, J = 11.5 Hz, 1H), 5.73 (d, J = 18.5 Hz, 1H), 6.69-6.75 (dd, J = 11.0, 6.5 Hz, 1H), 7.31 (d , J = 8.0 Hz, 2H), 7.39 (d, J = 8.0 Hz, 2H).

References

[1] Journal of the American Chemical Society, 2011, vol. 133, # 50, p. 20146 - 20148
[2] Reactive and Functional Polymers, 2014, vol. 81, # 1, p. 54 - 60
[3] Patent: WO2015/73882, 2015, A1. Location in patent: Page/Page column 10-11

(4-Vinylphenyl)methanol(1074-61-9)Related Product Information

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• VINYLBENZYL ALCOHOL
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