2-Propenoic acid, 3-[(4'-cyano[1,1'-biphenyl]-4-yl)oxy]propyl ester Chemical Properties

Boiling point:

499.8±40.0 °C(Predicted)

Density 

1.17±0.1 g/cm3 (20 ºC 760 Torr)

InChI

InChI=1S/C19H17NO3/c1-2-19(21)23-13-3-12-22-18-10-8-17(9-11-18)16-6-4-15(14-20)5-7-16/h2,4-11H,1,3,12-13H2

InChIKey

KFMJYBHOBTUCGH-UHFFFAOYSA-N

SMILES

C(OCCCOC1=CC=C(C2=CC=C(C#N)C=C2)C=C1)(=O)C=C

2-Propenoic acid, 3-[(4'-cyano[1,1'-biphenyl]-4-yl)oxy]propyl ester Usage And Synthesis

Chemical Properties

White solid.

Uses

2-Propenoic acid, 3-[(4'-cyano[1,1'-biphenyl]-4-yl)oxy]propyl ester can be used as a synthetic intermediate for polymerizable liquid crystal compounds such as displays.

Preparation

Intermediate A was obtained by mixing 9.8 g (50.0 mmol) 4-cyano-4'-hydroxybiphenol, 7.0 g (50.0 mmol) 3-bromo-1-propanol, 13.8 g (100 mmol) potassium carbonate, and 150 ml acetone. 12.0 g of the intermediate compound (A) obtained above was dissolved in 40 ml of THF along with 7.7 ml of triethylamine and a small amount of BHT and stirred at room temperature, in which a solution of 4.6 ml of acryloyl chloride in 40 ml of THF was dropped over 15 minutes under cooling on a water bath. After the dropping, the reaction solution was stirred for 30 minutes, after which the water bath was removed and stirring was continued overnight while returning to room temperature, followed by filtration of a precipitated TEA hydrochloride salt. About 3/4 of the THF was distilled off from the resulting filtrate, to which 50 ml of methylene chloride was added. The resulting organic phase was washed successively with 50 ml of a saturated sodium hydrogen carbonate aqueous solution, 50 ml of 0.5N-HCl and 50 ml of a saturated saline solution, and dried over magnesium sulfate, followed by distilling off the solvent to obtain a product. After recrystallization with ethanol, 6.0 g of 2-Propenoic acid, 3-[(4'-cyano[1,1'-biphenyl]-4-yl)oxy]propyl ester was obtained.