3-BROMO-4-HYDROXYBENZONITRILE Chemical Properties

Melting point:

155-159 °C(lit.)

Boiling point:

271.1±25.0 °C(Predicted)

Density 

1.79±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly, Heated)

pka

6.30±0.18(Predicted)

form 

Solid

color 

Off-White to Pale Beige

BRN 

2207020

InChI

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

InChIKey

HLHNOIAOWQFNGW-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2315-86-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36/37

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-BROMO-4-HYDROXYBENZONITRILE Usage And Synthesis

Chemical Properties

brown crystals or needles

Uses

3-Bromo-4-hydroxybenzonitrile is a reactant that has been used in the preparation of tetrazoles.

Synthesis

4-Hydroxybenzonitrile (III) (5.0 g, 0.042 mol) was dissolved in acetonitrile (50 mL) under nitrogen atmosphere. The reaction mixture was cooled to -15 °C and trifluoromethanesulfonic acid (CF3SO3H) (3.7 mL, 6.3 g, 0.042 mol) was slowly added. Maintaining the reaction temperature at -15 °C, N-bromosuccinimide (NBS) (8.2 g, 0.046 mol) was added in 6 additions in batches. After addition, the reaction mixture was returned to room temperature and continued to be stirred under nitrogen atmosphere for 4 h. The reaction process was monitored by thin-layer chromatography (TLC) (unfolding reagent: hexane/ethyl acetate = 75:25, detection method: UV and KMnO4 color development). When the raw materials were completely consumed, the reaction mixture was diluted with aqueous sodium carbonate (Na2CO3) and extracted with methyl tert-butyl ether (MTBE) (3 x 50 mL). The organic layers were combined, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to give 3-bromo-4-hydroxybenzonitrile (IV) as a white solid (7.7 g, 93% yield).1H NMR (DMSO-d6, 300 MHz, 300 K): δ=8.04 (d, J=2.2Hz, 1H), 7.63 (dd, J=2.2Hz, 8.5Hz, 8.5 Hz. 1H), 7.04 (d, J=8.5Hz, 1H).

References

[1] Patent: US9181298, 2015, B2. Location in patent: Page/Page column 33; Sheet 8
[2] Journal of Organic Chemistry, 2005, vol. 70, # 11, p. 4267 - 4271
[3] Patent: WO2010/142653, 2010, A1. Location in patent: Page/Page column 14
[4] Patent: CN103333134, 2016, B. Location in patent: Paragraph 0101; 0102
[5] RSC Advances, 2014, vol. 4, # 49, p. 25898 - 25903

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