2,5-Bis(trifluoromethyl)aniline Chemical Properties

Boiling point:

70-71 °C15 mm Hg(lit.)

Density 

1.467 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.432(lit.)

Flash point:

160 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Oil

pka

0.24±0.10(Predicted)

Specific Gravity

1.467

color 

Clear Colourless

BRN 

2653046

InChI

InChI=1S/C8H5F6N/c9-7(10,11)4-1-2-5(6(15)3-4)8(12,13)14/h1-3H,15H2

InChIKey

XWMVIJUAZAEWIE-UHFFFAOYSA-N

SMILES

C1(N)=CC(C(F)(F)F)=CC=C1C(F)(F)F

CAS DataBase Reference

328-93-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,T,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39-45-36

RIDADR 

2810

WGK Germany 

3

Hazard Note 

Toxic/Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214990

MSDS

• Language:English Provider:2,5-Bis(trifluoromethyl)aniline
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,5-Bis(trifluoromethyl)aniline Usage And Synthesis

Chemical Properties

Clear colorless liquid

Uses

2,5-Bis(trifluoromethyl)aniline is a haloalkul substituted aniline used in the preparation of anti-benign prostatic hyperplasia drug, Dutasteride (D735000).

Uses

2,5-Bis(trifluoromethyl)aniline may be used in chemical synthesis.

Synthesis

Example 8: To an autoclave was added 1.05 g of Raney nickel catalyst (10 wt%) and 100 mL of isopropanol followed by 10.0 g of 2,5-bis(trifluoromethyl)nitrobenzene. Hydrogen was passed under stirring until the pressure reached 5 kg/cm2 and the temperature was raised to 70 °C. The reaction was continued at 70-90°C for 8 hours. After completion of the reaction, the temperature was allowed to drop to room temperature, the hydrogen pressure was released, the catalyst was removed by filtration and the filtrate was washed with isopropanol. The filtrate was concentrated to give 6.42 g of 2,5-bis(trifluoromethyl)aniline in 73% yield and 99.4% GC purity. The structure of the product was confirmed by GC-MS, 1H-NMR and 19F-NMR analysis.

References

[1] Patent: EP1468983, 2004, A1. Location in patent: Page 6
[2] Journal of the American Chemical Society, 1953, vol. 75, p. 4967
[3] Patent: WO2011/150156, 2011, A2. Location in patent: Page/Page column 132

2,5-Bis(trifluoromethyl)aniline(328-93-8)Related Product Information

• N-Methylaniline
• 3-(Trifluoromethyl)benzaldehyde
• Acid Blue 93
• p-Toluidine
• 3-Aminobenzotrifluoride
• 2-(Trifluoromethyl)benzoic acid
• 4-Aminobenzotrifluoride
• 4-(Trifluoromethoxy)aniline
• 2-Fluoroaniline
• 2,5-Bis(trifluoromethyl)nitrobenzene
• Dutasteride
• N,N-Dimethyl-1,4-phenylenediamine
• 4-Fluoroaniline
• 3,3',5,5'-Tetramethylbenzidine dihydrochloride
• N,N-Dimethylaniline
• 2-Aminobenzotrifluoride
• Aniline
• o-Toluidine