3,4,5-Trifluoronitrobenzene Chemical Properties

Boiling point:

208.6±35.0 °C(Predicted)

Density 

1.517 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.486(lit.)

Flash point:

167 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

Light yellow to Yellow to Orange

BRN 

2455018

InChI

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

InChIKey

PTTUMBGORBMNBN-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

66684-58-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29049090

MSDS

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

3,4,5-Trifluoronitrobenzene Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

3,4,5-Trifluoronitrobenzene is a nitrobenzene derivative that has been shown to be stable in the environment. 3,4,5-Trifluoronitrobenzene has been detected in environmental samples and is considered to be a potential pollutant. This compound is not expected to bioaccumulate significantly due to its low water solubility. The liquid crystal properties of 3,4,5-trifluoronitrobenzene are also studied for potential application in display technologies.

Synthesis

The general procedure for the synthesis of 3,4,5-trifluoronitrobenzene from 2,3,4-trifluoro-6-nitroaniline was as follows: a solution of tert-butyl nitrite (340 mL) in N,N-dimethylformamide (DMF, 150 mL) was slowly added to a stirred solution of DMF (1 L) containing 6-nitro-2,3,4-trifluoroaniline (500 g). The reaction was carried out at 45-75 °C for 3 h under argon protection. After keeping the same temperature and continuing stirring for 1 h, the reaction mixture was treated with 20% aqueous hydrochloric acid solution (2 L). After cooling, steam distillation of the resulting solution gave 3,4,5-trifluoronitrobenzene as a yellow liquid, which was separated from the distillate (289 g, 62% yield). The purity of the resulting product was about 90% by gas chromatography (GC) analysis.1H NMR (δ): 8.13-7.92 (m, 2H).

References

[1] Patent: WO2004/37765, 2004, A1. Location in patent: Page 7; 8-9

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