4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE Chemical Properties

Melting point:

68-70°C

Boiling point:

195°C 1mm

Density 

1.129±0.06 g/cm3(Predicted)

Flash point:

195°C/1mm

storage temp. 

Sealed in dry,Room Temperature

BRN 

2702492

CAS DataBase Reference

1700-29-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

22

Safety Statements 

22-36/37

RIDADR 

3439

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

2926907090

MSDS

• Language:English Provider:ALFA

4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE Usage And Synthesis

Synthesis

4-Phenylmethoxy-3-methoxyphenylacetonitrile was prepared by reaction of 4-hydroxy-3-methoxyphenylacetonitrile (1.08 g, 6.60 mmol, 1.0 eq.) and benzyl bromide (1.24 g, 7.26 mmol, 1.1 eq.) in acetone (14 mL) according to the modified method of Imbri et al. First, K2CO3 (1.10 g, 7.92 mmol, 1.2 eq.) was added to the acetone solution of 4-hydroxy-3-methoxyphenylacetonitrile and the suspension was stirred for 10 min. Subsequently, benzyl bromide was added slowly dropwise via syringe. The reaction mixture was heated to reflux for 4 hours. Upon completion of the reaction, the suspension was separated by filtration and the precipitated solid was washed with acetone (10 mL). The filtrate was concentrated under reduced pressure and diluted with dichloromethane (DCM, 50 mL). The organic layer was washed sequentially with 2N NaOH (30 mL) and brine (30 mL) and then dried with Na2SO4. Finally, the solvent was removed by vacuum to afford the target product, 4-phenylmethoxy-3-methoxyphenylacetonitrile, as a yellow solid (1.67 g, 6.59 mmol, quantitative yield). The thin layer chromatography (TLC) Rf value of the product was 0.43 (cyclohexane/ethyl acetate, 2:1). The melting point was 65-66 °C. Nuclear magnetic resonance hydrogen (1H NMR, 400 MHz, CDCl3) and carbon (13C NMR, 100.6 MHz, CDCl3) data were consistent with the literature reports, confirming the structure of the product.

References

[1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 22, p. 6137 - 6148
[2] Chemistry - A European Journal, 2013, vol. 19, # 45, p. 15080 - 15083

4-BENZYLOXY-3-METHOXYPHENYLACETONITRILE(1700-29-4)Related Product Information

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• 2-Benzyloxyphenol
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