2-Fluoro-4-hydroxybenzonitrile Chemical Properties

Melting point:

123-125 °C (lit.)

Boiling point:

285.4±25.0 °C(Predicted)

Density 

1,45 g/cm³

storage temp. 

Sealed in dry,Room Temperature

solubility 

4.7g/l

pka

6.84±0.18(Predicted)

form 

powder to crystal

color 

White to Almost white

PH

4.2 (H2O, 20℃)(saturated aqueous solution)

BRN 

4741066

InChI

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

InChIKey

REIVHYDACHXPNH-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(O)C=C1F

CAS DataBase Reference

82380-18-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi,T

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-37/39

RIDADR 

3276

WGK Germany 

2

Hazard Note 

Irritant

HazardClass 

9

PackingGroup 

III

HS Code 

29269095

MSDS

• Language:English Provider:4-Cyano-3-fluorophenol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Fluoro-4-hydroxybenzonitrile Usage And Synthesis

Chemical Properties

Off-white Cryst

Uses

2-Fluoro-4-hydroxybenzonitrile may be used in the synthesis of 4-cyano-3-fluorophenyl 4-(hexadecyloxy) benzoate.

Uses

Intermediates of Liquid Crystals

General Description

2-Fluoro-4-hydroxybenzonitrile is a planar molecule. Its mol-ecules are arranged in linear chains via weak intermolecular O-HN hydrogen bonds.

Synthesis

General procedure for the synthesis of 2-fluoro-4-hydroxybenzonitrile from 4-bromo-2-fluorobenzonitrile: 4-bromo-2-fluorobenzonitrile (0.25 mmol), copper bromide (0.03 mmol), triethylamine (0.25 mmol, 1.0 eq.), formic acid (0.75 mmol, 3.0 eq.), and acetonitrile (179 mmol) were added to a reaction flask at room temperature. were used as reaction solvents. The reaction mixture was stirred at room temperature for 24 h under oxygen atmosphere. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, water (20 mL) and ethyl acetate (10 mL) were added to the reaction mixture for extraction, and the organic phases were combined and dried over anhydrous sodium sulfate. The dried organic phase was filtered and the filter cake was washed with ethyl acetate (5 mL × 3 times). Subsequently, the solvent was removed by rotary evaporator. The crude product was purified by column chromatography (eluent ratio: petroleum ether/ethyl acetate = 6:1) to afford the target product 2-fluoro-4-hydroxybenzonitrile in yellow liquid form in 82% yield.

References

[1] Organic Letters, 2018, vol. 20, # 3, p. 708 - 711
[2] Patent: CN107915586, 2018, A. Location in patent: Paragraph 0097-0100

2-Fluoro-4-hydroxybenzonitrile(82380-18-5)Related Product Information

• 3-Trifluoromethylphenol
• 2,4-Dichlorophenol
• 4-Hydroxybenzaldehyde
• Sodium cyanoborohydride
• ETHYL 2-CYANOACRYLATE
• 4-Fluorophenol
• Triclosan
• 4'-Hydroxyacetophenone
• 4-Hydroxybenzoic acid
• 2-Fluorophenol
• 2-Fluoro-4-hydroxybenzoic acid
• Methylparaben
• 4-Cyanophenol
• 4-Methoxyphenol
• 2'-Hydroxy-3-phenylpropiophenone
• 4-Hydroxybenzyl alcohol
• 2-Fluoro-4-methoxybenzonitrile
• 2-Fluoro-4-Cyano phenol