4-BROMO-2-HYDROXYBENZONITRILE Chemical Properties

Melting point:

160 °C

Boiling point:

295.1±25.0 °C(Predicted)

Density 

1.79±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

6.20±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C7H4BrNO/c8-6-2-1-5(4-9)7(10)3-6/h1-3,10H

InChIKey

PAHSHGVACWNGEY-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(Br)C=C1O

Safety Information

Hazard Codes 

Xi

RIDADR 

3439

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

2926907090

4-BROMO-2-HYDROXYBENZONITRILE Usage And Synthesis

Chemical Properties

white crystalline

Uses

4-Bromo-2-hydroxybenzonitrile is a benzonitrile derivative containing hydroxyl and bromine atom substituents at the 2 and 4 positions. The substance can be used to prepare indole derivatives or small molecule inhibitors (plasma kinin releasing enzyme inhibitors).

Synthesis

General procedure for the synthesis of 4-bromo-2-hydroxybenzonitrile from 4-bromo-2-fluorobenzonitrile: 2-fluoro-5-bromobenzonitrile (30 g, 152.3 mmol), potassium acetate (222.4 g, 228.5 mmol), and 18-crown-6 ether (60.4 g, 228.5 mmol) were dissolved in acetonitrile (400 mL) and heated and refluxed for 36 hours. After completion of the reaction, the mixture was cooled to room temperature, 2.5 N NaOH solution (200 mL) was added and stirred overnight at room temperature. The reaction mixture was extracted with ether and the organic layer was discarded. The aqueous layer was acidified with 6 N HCl and extracted with ethyl acetate. The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was purified by fast column chromatography (40% ethyl acetate/hexane) to afford 4-bromo-2-hydroxybenzonitrile as a light yellow foamy solid (24.45 g, 81% yield). NMR hydrogen spectrum (300 MHz, DMSO-d6): δ 7.13 (dd, J = 1.7, 8.3 Hz, 1H), 7.17 (d, J = 1.7 Hz, 1H), 7.61 (d, J = 8.3 Hz, 1H).

References

[1] Synthetic Communications, 2004, vol. 34, # 5, p. 751 - 758
[2] Heterocyclic Communications, 2011, vol. 17, # 1-2, p. 10 - 16
[3] Patent: US2004/14723, 2004, A1. Location in patent: Page/Page column 7
[4] Patent: EP2632465, 2015, B1. Location in patent: Paragraph 0416
[5] Patent: WO2008/25509, 2008, A1

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