2,5-Difluoronitrobenzene Chemical Properties

Melting point:

-11.7 °C (lit.)

Boiling point:

206.5 °C (lit.)

Density 

1.467 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.509(lit.)

Flash point:

194 °F

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid

color 

Clear yellow

Specific Gravity

1.467

Water Solubility 

insoluble

BRN 

2210200

InChI

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

InChIKey

XNJAYQHWXYJBBD-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

364-74-9(CAS DataBase Reference)

NIST Chemistry Reference

2,5-Difluoronitrobenzene(364-74-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

2810

WGK Germany 

3

RTECS 

CZ5715000

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29049090

MSDS

• Language:English Provider:1,4-Difluoro-2-nitrobenzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,5-Difluoronitrobenzene Usage And Synthesis

Chemical Properties

CLEAR YELLOW LIQUID

Uses

2,5-Difluoronitrobenzene was used in the synthesis of :

• N-alkylated 2-arylaminobenzimidazoles
• quinoxalinones
• N-(2-nitro-4-fluorophenyl)-l,2,3,4-tetrahydroisoquinoline

Synthesis

GENERAL STEPS: In a FEP or PFA reactor fitted with a PTFE-lined magnetic stir bar and connected to a gas scrubber bottle, substituted benzene (0.95-1.10 mmol), 1,1,1,3,3-pentafluorobutane (2 mL per mL of C6H5R), and BF3-Et2O (1.3-1.5 mmol/mmol C6H5R) were added. The mixture was stirred at 0-5 °C (ice bath) for 10-15 min, followed by batchwise addition of XeF2 (1.2-1.3 mmol/mmol C6H5R). After each addition, the mixture was stirred at 22-25 °C for 3-5 min and recooled. After the addition was completed, the dark solution was continued to be stirred at 22-25 °C for 15-30 min. At the end of the reaction, the reaction was quenched by the addition of 10% aqueous KHCO3, the upper organic layer was separated and filtered through a short column packed with silica gel (40-60 μm) and subsequently dried with magnesium sulfate. The final products were analyzed by 19F NMR and GC/MS. The major products are listed in the table and the others are as follows (with GC/MS data).

References

[1] Russian Journal of Organic Chemistry, 2016, vol. 52, # 10, p. 1400 - 1407
[2] Zh. Org. Khim., 2016, vol. 52, # 10, p. 1412 - 1419,8

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