5-Bromo-2-(trifluoromethoxy)aniline Chemical Properties

Boiling point:

230.2±35.0 °C(Predicted)

Density 

1.726±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

1.38±0.10(Predicted)

form 

liquid

color 

Pale yellow

InChI

InChI=1S/C7H5BrF3NO/c8-4-1-2-6(5(12)3-4)13-7(9,10)11/h1-3H,12H2

InChIKey

FOJWHUFRHXEUBA-UHFFFAOYSA-N

SMILES

C1(N)=CC(Br)=CC=C1OC(F)(F)F

Safety Information

Hazard Codes 

Xi

RIDADR 

UN2811

HS Code 

2922500090

5-Bromo-2-(trifluoromethoxy)aniline Usage And Synthesis

Description

5-Bromo-2-(trifluoromethoxy)aniline has a wide range of applications in scientific research. It is used as a reagent in organic synthesis and as a catalyst in polymerization reactions. It is also used as a building block for the synthesis of other organic compounds, such as pharmaceuticals and agrochemicals. It is also used in the synthesis of heterocyclic compounds and in the preparation of metal complexes.

Uses

5-Bromo-2-(trifluoromethoxy)aniline (5-BTA) is a drug with inhibitory activity against cell proliferation and has been shown to be effective in inhibiting the growth of certain cancer cells, such as those expressing tyrosine kinase isoforms. 5-BTA is also capable of blocking cell proliferation through inhibition of other enzymes (e.g., protein kinases). The oral Bioavailability of 5-BTA has been demonstrated in rats and mice. A2780 cells are human lung cancer cells with mutations in the gene encoding tyrosine kinase. Selectivity for tyrosine kinase isoforms was observed in vitro and in vivo.

Synthesis

Synthesis of 5-bromo-2-(trifluoromethoxy)aniline (1): to a solution of 4-bromo-2-nitro-1-(trifluoromethoxy)benzene (2.0 g, 7.0 mmol) in acetic acid (10.0 mL) was added powdered iron (1.0 g, 17.9 mmol) batchwise at 0-10 °C. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the acetic acid was removed by distillation and the residue was diluted with water and the pH was adjusted to alkaline with saturated sodium bicarbonate solution. Subsequently, the aqueous phase was extracted with ethyl acetate (2 x 50 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the brown colloidal solid product 1 (1.2 g, 70% yield).1H NMR (400 MHz, DMSO-d6): δ 5.68 (s, 2H), 6.65-6.66 (dd, J=2.4 Hz, 6.2 Hz, 1H), 6.95-6.96 (d, J=2.5 Hz. 1H), 7.01-7.01 (dd, J=1.4Hz, 8.6Hz, 1H). ms m/z (M+H): 256.3.

References

[1] Patent: WO2014/149164, 2014, A1. Location in patent: Paragraph 00758; 00892
[2] Patent: EP3150592, 2017, A1. Location in patent: Paragraph 0126; 0127; 0128

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