5-BROMO-2-HYDROXYBENZONITRILE Chemical Properties

Melting point:

158-163 °C

Boiling point:

282.8±25.0 °C(Predicted)

Density 

1.79

storage temp. 

Inert atmosphere,Room Temperature

solubility 

slightly sol. in Methanol

form 

powder to crystal

pka

6.60±0.18(Predicted)

color 

White to Light yellow

InChI

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

InChIKey

PVCONXMDUZOPJH-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

40530-18-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

26-36/37/39-24/25

RIDADR 

3439

WGK Germany 

3

HazardClass 

IRRITANT, IRRITANT-HARMFUL

HS Code 

29269090

5-BROMO-2-HYDROXYBENZONITRILE Usage And Synthesis

Chemical Properties

Off-white crystalline

Synthesis

Synthesis of 5-bromo-2-hydroxybenzonitrile: To a solution of 5-bromosalicylaldehyde (80.0 g, 0.40 mol) in formic acid was added hydroxylamine hydrochloride (36.0 g, 0.52 mol) and sodium form (37.0 g, 0.52 mol) in sequence. The reaction mixture was stirred at 100 °C for 7 hours. After completion of the reaction, the solvent was removed by evaporation and the residue obtained was dissolved in ethyl acetate. The organic layer was washed with water and dried. The solvent was again removed by evaporation and petroleum ether was added to the residue, and the precipitated crystals were filtered to give 5-bromo-2-hydroxybenzonitrile (75.2 g, 95% yield).1H-NMR (DMSO-d6) δ: 6.98 (d, J = 8.9 Hz, 1H), 7.65 (dd, J = 8.9,2.4 Hz, 1H), 7.86 (d, J = 2.4 Hz , 1H), 11.41 (s, 1H).

References

[1] Patent: EP2128136, 2009, A1. Location in patent: Page/Page column 7
[2] Heterocyclic Communications, 2009, vol. 15, # 5, p. 335 - 341
[3] Indian Journal of Heterocyclic Chemistry, 2010, vol. 20, # 2, p. 129 - 132
[4] Synthetic Communications, 1992, vol. 22, # 14, p. 2125 - 2128
[5] New Journal of Chemistry, 2000, vol. 24, # 7, p. 541 - 546

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