2-Fluoro-4-nitrophenol Chemical Properties

Melting point:

120-122 °C (lit.)

Boiling point:

281.2±25.0 °C(Predicted)

Density 

1.4306 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

5.67±0.22(Predicted)

color 

White to Light yellow

BRN 

1944995

InChI

InChI=1S/C6H4FNO3/c7-5-3-4(8(10)11)1-2-6(5)9/h1-3,9H

InChIKey

ORPHLVJBJOCHBR-UHFFFAOYSA-N

SMILES

C1(O)=CC=C([N+]([O-])=O)C=C1F

CAS DataBase Reference

403-19-0(CAS DataBase Reference)

EPA Substance Registry System

2-Fluoro-4-nitrophenol (403-19-0)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29089000

2-Fluoro-4-nitrophenol Usage And Synthesis

Chemical Properties

yellow crystalline powder

Uses

2-Fluoro-4-nitrophenol may be used in chemical synthesis.

General Description

2-Fluoro-4-nitrophenol is a derivative of m-fluoronitrobenzene. Crystal structure of complex of α-cyclodextrin with 2-fluoro-4-nitrophenol has been studied by the X-ray diffraction technique.

Synthesis

A. Synthesis of 2-fluoro-4-nitrophenol 2-Fluorophenol (32.3 g, 0.288 mol) was dissolved in dichloromethane under ice-salt bath conditions and cooled to -10 °C. 90% nitric acid (22 g, 0.31 mol HNO3) was added slowly, and the titration rate was controlled to maintain the reaction temperature at about -5 °C, and the titration process lasted for 1 hour. After completion of the dropwise addition, the reaction mixture was continued to be stirred at 0°C for 1 hour. At the end of the reaction, the precipitate was collected by filtration and washed several times with cold dichloromethane. Analysis by GC and thin layer chromatography (silica gel, 7:3 hexane-acetone) showed that the product was mainly a single compound and the by-products generated in the reaction were of low polarity and volatility. The solid was dissolved in ether, washed with water, dried over anhydrous magnesium sulfate, and the solvent evaporated. The resulting solid was recrystallized with methylcyclohexane to give 13 g of a pale yellow solid with a melting point of 119°-121°C. Nuclear magnetic resonance (CDCl3) analysis confirmed that the product was 2-fluoro-4-nitrophenol. B. Isolation of 2-fluoro-6-nitrophenol The dichloromethane mother liquor was washed with water, dried over anhydrous magnesium sulfate and the solvent was evaporated. The resulting solid was ground with boiling hexane (3 x 150 ml) to effectively remove the least polar and volatile by-products. The hexane solution was treated with activated carbon, filtered and concentrated to about 300 ml, and cooled to give 13.5 g (30% yield) of 2-fluoro-6-nitrophenol as a yellow solid with a melting point of 70°-86° C. The solid was then dried with water.

References

[1] Patent: US4750931, 1988, A
[2] Patent: EP142328, 1991, B1

2-Fluoro-4-nitrophenol(403-19-0)Related Product Information

• 1-Fluoro-2-nitrobenzene
• 2,6-DINITROPHENOL
• 4-Fluorophenol
• 2-Fluoro-4-nitrobenzoic acid
• 3-Nitrophenol
• 4-Fluoronitrobenzene
• 4-Nitrophenol
• 2,5-DINITROPHENOL
• 2-Nitrophenol
• Fluorine
• PICRIC ACID
• 3-FLUORO-4-NITROPHENOL (POWDER),3-FLUORO-4-NITROPHENOL (SOLID),3-Fluoro-4-nitrophenol99%,3-FLUORO-4-NITROPHENOL
• Nitrophenol
• 2,6-Difluoro-4-nitrophenol
• 4-Fluoro-2-nitrophenol99%,4-FLUORO-2-NITROPHENOL, 98+%,4-FLUORO-2-NITROPHENOL,4-Fluoro-2-nitrophenol 99%
• 2-BROMO-4-FLUORO-5-NITROPHENOL
• 2-Fluoro-3-nitrophenol,3-FLUORO-2-NITROPHENOL
• 4-FLUORO-3-NITROPHENOL 98%,4-Fluoro-3-nitrophenol