1,2,3-Trifluoro-4-nitrobenzene Chemical Properties

Boiling point:

92 °C/20 mmHg (lit.)

Density 

1.541 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.492(lit.)

Flash point:

200 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

Light yellow to Yellow to Orange

Specific Gravity

1.541

BRN 

2449746

InChI

InChI=1S/C6H2F3NO2/c7-3-1-2-4(10(11)12)6(9)5(3)8/h1-2H

InChIKey

ARCACZWMYGILNI-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

771-69-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39-24/25

RIDADR 

UN2810

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29042090

MSDS

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1,2,3-Trifluoro-4-nitrobenzene Usage And Synthesis

Uses

2,3,4-Trifluoronitrobenzene is a useful research chemical.

Chemical Properties

clear yellow liquid after melting

Uses

2,3,4-Trifluoronitrobenzene was employed as starting reagent in the synthesis of ofloxacin. It was also used in the synthesis of the third generation quinolones antibacterial drugs.

General Description

2,3,4-Trifluoronitrobenzene is a fluoronitrobenzene and its biotransformation under methanogenic conditions has been studied by semicontinuous and batch tests. 2,3,4-Trifluoronitrobenzene is an important pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of 2,3,4-trifluoronitrobenzene from 2,3,4-trichloronitrobenzene: (2) 240 g of DMSO and 120 g of 2,3,4-trichloronitrobenzene were added to an anhydrous reaction flask with stirring turned on, and the temperature was raised to 75-80 °C under reduced pressure with continuous stirring for 2 hours. Subsequently, 76.8 g of KF and 12 g of TBAB were added to the reaction system and dehydrated under reduced pressure at 75-80 °C for 2 h until no droplets of water fell from the distillation head. (3) The reaction system was slowly warmed up to 180 °C to start the reaction. The reaction process was monitored by gas chromatography (GC), and the reaction was completed when the content of both 2-fluoro-3,4-dichloronitrobenzene and 2,3-dichloro-4-fluoronitrobenzene decreased to less than 0.2% after 10 h. The reaction was completed when the content of 2-fluoro-3,4-dichloronitrobenzene and 2,3-dichloro-4-fluoronitrobenzene dropped below 0.2%. The reaction mixture was cooled to 70-75 °C, filtered, and the filtrate was vacuum distilled and reintroduced into the anhydrous reaction unit. 46 g of KF and 12 g of TBAF were added and dehydrated under reduced pressure at 75-80 °C for 2 h until no water droplets appeared in the distillation head. The reaction temperature was set to 120 °C and ultrasonic power to 20 kHz and the reaction was continued. The reaction was monitored by GC and completed after 2 hours. The reaction mixture was cooled to 70-75°C and filtered and the filtrate was distilled to separate DMSO from the product. The final yield of 2,3,4-trifluoronitrobenzene was 99.7%.

References

[1] Patent: CN107325001, 2017, A. Location in patent: Paragraph 0028-0029; 0031-0034; 0036-0039; 0041-0044; 0046

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