3-Fluoro-4-hydroxybenzonitrile Chemical Properties

Melting point:

133-135°C

Boiling point:

253.9±25.0 °C(Predicted)

Density 

1.34±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

6.58±0.18(Predicted)

color 

White to Almost white

InChI

InChI=1S/C7H4FNO/c8-6-3-5(4-9)1-2-7(6)10/h1-3,10H

InChIKey

DPSSSDFTLVUJDH-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

405-04-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39-37/39

RIDADR 

3439

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

2926907090

3-Fluoro-4-hydroxybenzonitrile Usage And Synthesis

Uses

3-Fluoro-4-hydroxybenzonitrile is an important organic intermediate, mainly used in the preparation of pharmaceuticals and pesticides, and has wide applications in the manufacture of dyes, engineering plastics and photosensitive materials.

Chemical Properties

Off-white Crysstalline

Synthesis

The general procedure for the synthesis of 3-fluoro-4-hydroxybenzonitrile using 3-fluoro-4-methoxybenzonitrile as starting material was as follows: to a solution of 3-fluoro-4-methoxybenzonitrile (15.6 g, 0.103 mol) in dichloromethane (100 mL) was slowly added boron tribromide (BBr3, 20 mL, 0.211 mol) at 0 °C. The reaction mixture was refluxed under nitrogen protection for 3 days. Upon completion of the reaction, the reaction was quenched with ice water and extracted with dichloromethane. The organic layers were combined, washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give 13.3 g of gray solid product in 94% yield. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.38-7.42 (m, 2H), 7.09 (dd, J = 8.8 Hz, 8.4 Hz, 1H), 5.68 (s, 1H).

References

[1] Patent: WO2013/97773, 2013, A1. Location in patent: Paragraph 0159; 0277
[2] Helvetica Chimica Acta, 1984, vol. 67, p. 1572 - 1579
[3] Patent: WO2005/123748, 2005, A1. Location in patent: Page/Page column 85-86
[4] Patent: WO2006/135316, 2006, A1. Location in patent: Page/Page column 59
[5] Patent: WO2006/137770, 2006, A1. Location in patent: Page/Page column 34

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