2-Fluoro-5-nitroaniline Chemical Properties

Melting point:

97-100 °C (lit.)

Boiling point:

295.5±20.0 °C(Predicted)

Density 

1.3822 (estimate)

Flash point:

196 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Crystalline Powder

pka

1.13±0.10(Predicted)

color 

Ochre-yellow to light brown

Water Solubility 

Slightly soluble

BRN 

2803491

InChI

InChI=1S/C6H5FN2O2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H,8H2

InChIKey

KJVBJICWGQIMOZ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

369-36-8(CAS DataBase Reference)

NIST Chemistry Reference

2-Fluoro-5-nitroaniline(369-36-8)

EPA Substance Registry System

Benzenamine, 2-fluoro-5-nitro- (369-36-8)

Safety Information

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38

Safety Statements 

16-26-36

RIDADR 

UN 1325 4.1/PG 2

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29214210

MSDS

• Language:English Provider:2-Fluoro-5-nitroaniline
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Fluoro-5-nitroaniline Usage And Synthesis

Chemical Properties

ochre-yellow to light brown crystalline powder

Uses

It is employed as pharmaceutical intermediate.

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 6141, 1990 DOI: 10.1016/S0040-4039(00)97008-4

Synthesis

The general procedure for the synthesis of 2-fluoro-5-nitroaniline from 2,4-dinitrofluorobenzene is as follows: 18.61 g (0.10 mol) of 2,4-dinitrofluorobenzene, 0.5 g of 5% palladium-carbon catalyst, 100 mL of glacial acetic acid, and 100 mL of anhydrous ethanol were added to a 500 mL Parr hydrogenation unit. The device was equipped with a thermocouple and a cooling jacket. During the reaction, the temperature of the reaction mixture was maintained at 20-25°C, the hydrogen pressure was maintained at 370 psi, and the reaction time was 2.5 hours. Upon completion of the reaction, the reaction mixture was poured into 400 mL of water. It was extracted twice with 200 mL of dichloromethane, the organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure and the resulting residue was filtered through a silica gel pad and eluted with dichloromethane. The eluate was concentrated again under reduced pressure and the residue was further purified by column chromatography using dichloromethane:heptane (80:20, v/v) as eluent. Finally, the solvent was evaporated under reduced pressure to give 2.75 g of 2-fluoro-5-nitroaniline in 17.6% yield.

References

[1] Patent: US5105012, 1992, A
[2] Recueil des Travaux Chimiques des Pays-Bas, 1916, vol. 35, p. 142
[3] Chem. Zentralbl., 1913, vol. 84, # II, p. 760
[4] Patent: US5105012, 1992, A
[5] Patent: US5105012, 1992, A

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