4-PHENOXYPHTHALONITRILE Chemical Properties

Melting point:

98-100 °C(lit.)

Boiling point:

399.8±37.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder, crystals or chunks

Appearance

Off-white to yellow Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

4-PHENOXYPHTHALONITRILE Usage And Synthesis

Uses

4-Phenoxyphthalonitrile is a C4-substituted phthalonitrile with monoamine oxidase inhibitory activity. 4-Phenoxyphthalonitrile is used in organic pigments and dyes. Dyes and metabolites.

Synthesis

General procedure for the synthesis of 4-phenoxyphthalonitrile from 4-nitrophthalonitrile and phenol: To a solution of tetrahydrofuran (THF, 15 mL) containing sodium hydride (NaH, 0.15 g) and phenol (0.353 g, 0.0375 mol), slowly add 4-nitrophthalonitrile (0.50 g, 0.0028 mol) to the THF (15 mL ) solution. The reaction mixture was heated to reflux for 8 hours. Upon completion of the reaction, 1,2-diisocyano-4-phenoxybenzene (8) was obtained by filtration and the solid was washed with ethyl acetate. The filtrate and washings were combined and the solvent was removed by evaporation under reduced pressure. The white precipitate obtained was purified by fast column chromatography using ethyl acetate: hexane (1:4) as eluent. The yield was 0.737 g in 86.4% with an Rf value of 0.36 (ethyl acetate: hexane, 1:4).1H NMR (300 MHz, CDCl3) δ 0.90 (s, 2H), 3.46 (m, 5H, CH), 7.07 (m, 3H, ArH).13C NMR (300 MHz, CDCl3) δ 71.01, 117.45, 119.69, 119.92, 126.95, 127.34, 134.43, 135.20.

References

[1] Asian Journal of Chemistry, 2017, vol. 29, # 3, p. 489 - 495
[2] Russian Journal of Organic Chemistry, 2006, vol. 42, # 4, p. 603 - 606
[3] Journal of Photochemistry and Photobiology A: Chemistry, 2010, vol. 209, # 2-3, p. 232 - 237
[4] Bioorganic Chemistry, 2012, vol. 40, # 1, p. 114 - 124
[5] Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 6.2, p. 964 - 967

4-PHENOXYPHTHALONITRILE(38791-62-7)Related Product Information

• Hydroquinone
• 3-PHENOXYPHTHALONITRILE
• 4-(1H-1,2,3-benzotriazol-1-yl)-5-phenoxyphthalonitrile
• 3-PHENOXYPHTHALONITRILE 98,3-PHENOXYPHTHALONITRILE 98%
• Phthalonitrile
• 4-METHOXYPHTHALONITRILE
• 3-Methoxybenzonitrile
• 3-PHENOXYBENZONITRILE
• 4-(4-ALPHA-CUMYLPHENOXY)PHTHALONITRILE
• 4-METHOXY-2-METHYLBENZONITRILE
• 4-(4-FORMYLPHENOXY)PHTHALONITRILE
• 4-Hydroxyphthalonitrile
• 3-Cyanophenol
• 4-(2',6'-DIMETHYLPHENOXY)PHTHALONITRILE
• 4-PHENOXYPHTHALONITRILE
• 4-PHENOXYBENZONITRILE