1-BOC-5-CYANOINDOLE

1-BOC-5-CYANOINDOLE Property

Melting point:

128-129 °C(Solv: ethanol (64-17-5); hexane (110-54-3))

Boiling point:

386.4±34.0 °C(Predicted)

Density 

1.12±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

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.

1-BOC-5-CYANOINDOLE Chemical Properties,Usage,Production

Synthesis

In a 100 mL round bottom flask, 5-cyanoindole (2.0 g, 14.07 mmol) was dissolved in 20 mL of anhydrous tetrahydrofuran (THF). To this solution, 4-dimethylaminopyridine (DMAP, 0.86 g, 7.03 mmol) was added and the mixture was stirred for 0.5 h at room temperature. Subsequently, di-tert-butyl dicarbonate (Boc2O, 3.07 g, 14.07 mmol) was added and the reaction continued to be stirred for 2 hours. After completion of the reaction, the reaction was quenched with water and extracted with ether (2×). The organic layers were combined, washed sequentially with 1N hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate (MgSO4) and concentrated to give 1-Boc-5-cyanoindole (3.26 g, 96% yield) as a white solid. The product was characterized by 1H NMR (DMSO-d6): δ 8.20-8.14 (m, 2H), 7.83 (d, 1H), 7.70 (d, 1H), 6.80 (d, 1H), 1.63 (s, 9H).

References

[1] Synthesis, 2009, # 21, p. 3617 - 3632
[2] Journal of Organic Chemistry, 2002, vol. 67, # 21, p. 7551 - 7552
[3] Patent: WO2004/43950, 2004, A1. Location in patent: Page 134
[4] Patent: WO2005/51957, 2005, A1. Location in patent: Page/Page column 54-55
[5] Patent: WO2011/60389, 2011, A1. Location in patent: Page/Page column 98-99