M-HYDROXY BENZYL CYANIDE Chemical Properties

Melting point:

53 °C

Boiling point:

305.5±17.0 °C(Predicted)

Density 

1.167±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

9.51±0.10(Predicted)

color 

White to Orange to Green

Safety Information

HS Code 

2926.90.5050

M-HYDROXY BENZYL CYANIDE Usage And Synthesis

Uses

2-(3-Hydroxyphenyl)acetonitrile is used in preparation of Pyrrolidine Sulfonamide compounds as TRPV4 antagonists.

Synthesis

Step 1: Dissolve 2-(3-methoxyphenyl)acetonitrile (2 g, 13.59 mmol) in 13 mL of anhydrous dichloromethane under nitrogen protection and cool to 0°C. A 1 M solution of boron tribromide in dichloromethane (28.54 mL, 28.54 mmol) was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was stirred at room temperature for 20 hours. After completion of the reaction, the mixture was poured into ice water and extracted three times with dichloromethane. The organic phases were combined, washed with brine and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the crude product was purified by silica gel column chromatography using petroleum ether/ethyl acetate (80/20) as eluent to give 1.28 g (71% yield) of 2-(3-hydroxyphenyl)acetonitrile.

References

[1] Patent: US2006/142553, 2006, A1. Location in patent: Page/Page column 11 - 12
[2] Patent: WO2008/46598, 2008, A1. Location in patent: Page/Page column 57
[3] Patent: WO2013/651, 2013, A1. Location in patent: Page/Page column 35; 55
[4] Patent: US2014/88074, 2014, A1. Location in patent: Paragraph 0286; 0287; 0524; 0525
[5] Patent: US6180627, 2001, B2

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