2-tert-butyl-5-nitro-1H-indole

2-tert-butyl-5-nitro-1H-indole Property

Boiling point:

377.0±22.0 °C(Predicted)

Density 

1.209

storage temp. 

Sealed in dry,Room Temperature

pka

15.98±0.30(Predicted)

InChI

InChI=1S/C12H14N2O2/c1-12(2,3)11-7-8-6-9(14(15)16)4-5-10(8)13-11/h4-7,13H,1-3H3

InChIKey

KWEGNNIENUBTCE-UHFFFAOYSA-N

SMILES

N1C2=C(C=C([N+]([O-])=O)C=C2)C=C1C(C)(C)C

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-tert-butyl-5-nitro-1H-indole Chemical Properties,Usage,Production

Synthesis

The reaction was carried out in the presence of copper(I) iodide (1.2 mg, 6.3 μmol) in DMF (45 mL) at reflux for 6 h. The reaction was carried out in the presence of 2-(3,3-dimethyl-1-butyn-1-yl)-4-nitroaniline (2.7 g, 12.4 mmol). Upon completion of the reaction, volatiles were removed by distillation under reduced pressure and the black residue obtained was purified by silica gel column chromatography (eluent: 20% ethyl acetate/hexane). The target product was collected and ground with hexane to give 2.34 g (87% yield) of 2-tert-butyl-5-nitroindole as a yellow crystalline solid. The product was confirmed by 1H NMR (CDCl3): δ 8.51 (d, J = 1.9 Hz, 1H), 8.33 (br s, 1H), 8.07 (dd, J = 8.9, 2.3 Hz, 1H), 7.35 (d, J = 8.8 Hz, 1H), 6.44 (d, J = 1.9 Hz, 1H), 1.44 (s, 9H). Mass spectrometry (MS) showed a molecular ion peak m/z of 219 ([MH]+).

References

[1] Patent: WO2004/35571, 2004, A1. Location in patent: Page 25