2,6-Difluoronitrobenzene Chemical Properties

Melting point:

0C

Boiling point:

91-92 °C/11 mmHg (lit.)

Density 

1.503 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.494(lit.)

Flash point:

190 °F

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to lump to clear liquid

color 

Light yellow to Yellow to Green

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C6H3F2NO2/c7-4-2-1-3-5(8)6(4)9(10)11/h1-3H

InChIKey

SSNCMIDZGFCTST-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

19064-24-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

16-26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29049090

MSDS

• Language:English Provider:SigmaAldrich

2,6-Difluoronitrobenzene Usage And Synthesis

Uses

1,3-Difluoro-2-nitrobenzene is a useful chemical reagent.

Chemical Properties

Light yellow to dark yellow solid

Uses

2,6-Difluoronitrobenzene may be used in the preparation of secondary amine precursors, required for the synthesis of two families of nitric oxide donors.

General Description

2,6-Difluoronitrobenzene is an organic building block. Molecular structure, conformation and potential to internal rotation of 2,6-difluoronitrobenzene been studied by gas-phase electron diffraction (GED), MP2 ab initio, and by B3LYP density functional calculations.

Synthesis

Step 1: A mixture of sodium perborate tetrahydrate (65 g, 422 mmol) in glacial acetic acid (250 mL) was stirred at 80 °C. 2,6-Difluoroaniline (11.0 g, 85 mmol) was dissolved in glacial acetic acid (50 mL) and slowly added to the above mixture. The reaction temperature was maintained between 80-90°C for 1 hour. The cooled reaction mixture was poured into water and extracted twice with ether. The organic layers were combined, washed with dilute sodium bicarbonate solution, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was purified by a Biotage fast chromatography system (FlasH90i, silica gel column, 10% THF/hexane as eluent) and the product was washed with hexane to give 2,6-difluoronitrobenzene (7.0 g, 52% yield). Mass spectrum (ESI) m/z 160 ([M + H]+).

References

[1] Patent: US2005/222148, 2005, A1. Location in patent: Page/Page column 58
[2] Patent: US2008/153873, 2008, A1. Location in patent: Page/Page column 20
[3] Journal of Organic Chemistry, 1992, vol. 57, # 21, p. 5577 - 5585
[4] European Journal of Organic Chemistry, 2006, # 5, p. 1109 - 1112
[5] Patent: US2006/9509, 2006, A1. Location in patent: Page/Page column 8

2,6-Difluoronitrobenzene(19064-24-5)Related Product Information

• 1-Fluoro-2-nitrobenzene
• 4-Fluoronitrobenzene
• 2,4-Dinitrophenylhydrazine
• 1,3-Dinitrobenzene
• 3,4-Difluoronitrobenzene 99%,3,4-DIFLUORONITROBENZENE,3,4-Difluoronitrobenzene99%,4-Difluoronitrobenzene
• Nitrobenzene
• PENTAFLUORONITROBENZENE
• 2,3,4,6-TETRAFLUORONITROBENZENE
• 1,3,5-Trifluoro-2-nitrobenzene
• 2,3,5,6-TETRAFLUORONITROBENZENE
• 5-CHLORO-2,4-DIFLUORONITROBENZENE
• 2-Acetonyloxo-3,4-difluoronitrobenzene
• 2-CHLORO-3,4-DIFLUORONITROBENZENE,2-Chloro-3,4,-difluoronitrobenzene96%,1-Chloro-2,3-difluoronitrobenzene,2-Chloro-3,4,-difluoronitrobenzene 96%
• 2,3-DIFLUORONITROBENZENE
• 3-CHLORO-4,5-DIFLUORONITROBENZENE,4-CHLORO-4,5-DIFLUORONITROBENZENE
• 2-METHOXY-3,4-DIFLUORONITROBENZENE
• 3-Chloro-2,4-difluoronitrobenzene 97%,3-CHLORO-2,4-DIFLUORONITROBENZENE,3-Chloro-2,4-difluoronitrobenzene97%
• 1,3-DIFLUORO-5-METHOXY-2-NITRO-BENZENE