2-Fluoro-6-nitrophenol Chemical Properties

Melting point:

92-94°C

Boiling point:

201.5±20.0 °C(Predicted)

Density 

1.511±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

5.67±0.24(Predicted)

color 

Light yellow to Yellow to Orange

BRN 

1870307

InChI

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

InChIKey

HIGRXCJEFUYRNW-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

1526-17-6(CAS DataBase Reference)

EPA Substance Registry System

2-Fluoro-6-nitrophenol (1526-17-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37/39-36/37

RIDADR 

2811

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

29089990

MSDS

• Language:English Provider:2-Fluoro-6-nitrophenol
• Language:English Provider:ALFA

2-Fluoro-6-nitrophenol Usage And Synthesis

Uses

2-Fluoro-6-nitrophenol has antifungal- and high plant-growth-regulating activity.

Synthesis

A. Synthesis of 2-fluoro-4-nitrophenol To a stirred dichloromethane solution of 2-fluorophenol (32.3 g, 0.288 mol) was slowly added 90% nitric acid (1 g, 0.31 mol HNO3) in an ice-salt bath cooled to -10°C. The addition process was controlled to be completed in 1 hour. During the reaction, the temperature was maintained at about -5 °C. After the addition was completed, stirring was continued 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 that the by-products produced in the reaction were of low polarity and volatility. The solid was dissolved in ether, washed with water, dried (MgSO4) 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. NMR (CDCl3) analysis confirmed the product as 2-fluoro-4-nitrophenol. The dichloromethane mother liquor was treated, washed with water, dried (MgSO4) and the solvent evaporated. The solid obtained was ground with boiling hexane (3 x 150 ml) to effectively remove the least polar and highly volatile reaction by-products. The hexane solution was treated with activated charcoal, filtered and concentrated to about 300 ml and cooled to give 13.5 g (30% yield) of the by-product 2-fluoro-6-nitrophenol as a yellow solid with a melting point of 70°-86 °C.

References

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

2-Fluoro-6-nitrophenol(1526-17-6)Related Product Information

• 2-FLUORO-6-NITRO-PHENYLAMINE
• 2-Fluoro-6-nitrobenzoic acid
• 2-Fluoro-6-nitroanisole
• 2,3-Difluoro-6-nitroanisole
• 2,3-DIFLUORO-6-NITROPHENOL
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• 2,3-DIFLUORO-6-NITROANISOLE
• 4-Nitrophenol
• 3-Nitrophenol
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