2-Nitro-4-fluorophenol Chemical Properties

Melting point:

75-77 °C (lit.)

Boiling point:

234.1±20.0 °C(Predicted)

Density 

1.4306 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

6.76±0.14(Predicted)

color 

Orange to Green to Amber

BRN 

1950412

InChI

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

InChIKey

ZHRLVDHMIJDWSS-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

394-33-2(CAS DataBase Reference)

NIST Chemistry Reference

4-Fluoro-2-nitrophenol(394-33-2)

EPA Substance Registry System

4-Fluoro-2-nitrophenol (394-33-2)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29089000

MSDS

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

2-Nitro-4-fluorophenol Usage And Synthesis

Chemical Properties

yellow crystalline powder

Uses

4-Fluoro-2-nitrophenol may be used in the preparation of 5-fluoro-2-methoxyanilineand 5-fluoro-2-hydroxyaniline.

General Description

4-Fluoro-2-nitrophenol is formed during iron(III) nitrate nonahydrate activated by tungstophosphoric acid cesium salt catalyzed nitration of 4-fluorophenol.

Synthesis

The general procedure for the synthesis of 2-nitro-4-fluorophenol from 4-fluorophenol was as follows: silica-loaded Al(NO3)3-9H2O (1 mmol) was added to a solution of 4-fluorophenol (1 mmol) in acetone (5 mL) and the reaction mixture was stirred at room temperature. The reaction process was monitored by TLC. Upon completion of the reaction, the reaction mixture was filtered and the silica residue was washed with ethyl acetate (25 mL). The filtrate and washings were combined and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (100-200 mesh) to give 2-nitro-4-fluorophenol (95%) and 4-nitro-4-fluorophenol (3%).

References

[1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1983, p. 75 - 82
[2] Synthetic Communications, 1997, vol. 27, # 19, p. 3301 - 3311
[3] Synlett, 2003, # 2, p. 191 - 194
[4] Synthetic Communications, 2005, vol. 35, # 2, p. 263 - 270
[5] Synthetic Communications, 1998, vol. 28, # 15, p. 2773 - 2781

2-Nitro-4-fluorophenol(394-33-2)Related Product Information

• 2,6-DINITRO-4-FLUOROPHENOL
• 2-Nitro-4-fluorophenol
• 4-Fluoro-2-nitroanisole
• 5-FLUORO-2-NITROPHENOL,2-NITRO-5-FLUOROPHENOL,6-Nitro-3-fluorophenol,2-Nitro-5-Fluorophenol
• 2-Fluoro-6-nitrophenol
• 4-Fluoro-3-nitrophenol
• 2-nitro-3-fluorophenol
• Nitrophenol
• 4-Fluorophenol
• 2-Nitrophenol
• 3-(4-FLUORO-2-NITROPHENOXY)-N-METHYL-2-THIOPHENECARBOXAMIDE
• 3-(4-FLUORO-2-NITROPHENOXY)-N-[3-(TRIFLUOROMETHYL)PHENYL]-2-THIOPHENECARBOXAMIDE
• 4-fluoro-2-nitrophenyl 4-methylbenzenecarboxylate
• N-(2,5-DIMETHOXYPHENYL)-3-(4-FLUORO-2-NITROPHENOXY)-2-THIOPHENECARBOXAMIDE
• 3-(4-FLUORO-2-NITROPHENOXY)-N,N-DIMETHYL-2-THIOPHENECARBOXAMIDE
• N-(4-CHLOROPHENYL)-3-(4-FLUORO-2-NITROPHENOXY)-2-THIOPHENECARBOXAMIDE
• N-ALLYL-3-(4-FLUORO-2-NITROPHENOXY)-2-THIOPHENECARBOXAMIDE
• 4-FLUORO-2-NITROPHENYL 4-CHLOROBENZENECARBOXYLATE