1H-Indole, 4-broMo-6-(trifluoroMethyl)- Chemical Properties

Boiling point:

298.1±35.0 °C(Predicted)

Density 

1.742±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

14.66±0.30(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C9H5BrF3N/c10-7-3-5(9(11,12)13)4-8-6(7)1-2-14-8/h1-4,14H

InChIKey

GVQHXKQOACYLJU-UHFFFAOYSA-N

SMILES

N1C2=C(C(Br)=CC(C(F)(F)F)=C2)C=C1

1H-Indole, 4-broMo-6-(trifluoroMethyl)- Usage And Synthesis

Uses

1H-Indole, 4-bromo-6-(trifluoromethyl)- can be used as a research compound for its unique reactivity due to the presence of both the halogen and the highly electronegative trifluoromethyl group.

Synthesis

A solution of 3-bromo-2-ethynyl-5-(trifluoromethyl)aniline (7.54 g, 28.6 mmol) was slowly added dropwise from its N-methylpyrrolidone (50 mL) solution to an N-methylpyrrolidone (200 mL) solution of potassium tert-butoxide (6.41 g, 57.1 mmol) at 0°C. The reaction mixture was stirred at room temperature for 4 hours. Subsequently, the reaction mixture was poured into brine (500 mL) and extracted with ethyl acetate (4 x 50 mL). The organic layers were combined, washed with brine (100 mL), dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography using a 10% to 25% ethyl acetate/hexane gradient elution to afford 4-bromo-6-trifluoromethyl-1H-indole (7.16 g, 95% yield) as a brown oil. The product was confirmed by 1H-NMR (CDCl3, 400 MHz) and LC/MS (HPLC Method 4): 1H-NMR δ 8.54 (bs, 1H), 7.63 (s, 1H), 7.53 (s, 1H), 7.40 (t, J = 2.8Hz, 1H), 6.66 (t, J = 2.8Hz, 1H); LC/MS: tR = 3.280min, 264.12 (MH)+.

References

[1] Patent: US2009/18132, 2009, A1. Location in patent: Page/Page column 85; 86
[2] Patent: US2015/266872, 2015, A1. Location in patent: Paragraph 0668; 0669
[3] Patent: EP2982670, 2016, A1

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