3-bromo-5-nitro-1H-indole

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3-bromo-5-nitro-1H-indole Basic information
Product Name:3-bromo-5-nitro-1H-indole
Synonyms:3-bromo-5-nitro-1H-indole;3-Bromo-5-nitroindole;1H-Indole, 3-bromo-5-nitro-
CAS:525593-33-3
MF:C8H5BrN2O2
MW:241.04
EINECS:
Product Categories:
Mol File:525593-33-3.mol
3-bromo-5-nitro-1H-indole Structure
3-bromo-5-nitro-1H-indole Chemical Properties
Melting point 191-194 °C
Boiling point 417.6±25.0 °C(Predicted)
density 1.855
storage temp. 2-8°C
pka13.58±0.30(Predicted)
AppearanceWhite to yellow Solid
Safety Information
MSDS Information
3-bromo-5-nitro-1H-indole Usage And Synthesis
Synthesis
5-Nitroindole

6146-52-7

3-bromo-5-nitro-1H-indole

525593-33-3

Step A: A solution of pyridinium bromide (10.99 g, 34.3 mmol) in pyridine (200 mL) was slowly added dropwise to a solution of pyridinium bromide (10.99 g, 34.3 mmol) in pyridine (200 mL) of 5-nitroindole (5.00 g, 30.8 mmol) at -40 °C and under nitrogen protection. After the dropwise addition was completed, the reaction mixture was continued to be stirred at 0°C for 5 minutes. Subsequently, the reaction mixture was diluted with water (200 mL) at 0 °C and extracted with ether (200 mL). The organic layer was washed sequentially with 6 M hydrochloric acid (300 mL), 5% sodium bicarbonate solution (300 mL) and saturated saline (300 mL). The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent to give 3-bromo-5-nitroindole as a yellow powder with 80% purity containing 20% 5-nitroindole (6.80 g, 74% yield).

References[1] Tetrahedron Letters, 2003, vol. 44, # 20, p. 3927 - 3930
[2] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 17, p. 5965 - 5980
[3] RSC Advances, 2016, vol. 6, # 93, p. 90031 - 90034
[4] Tetrahedron Letters, 2015, vol. 56, # 9, p. 1096 - 1098
[5] Patent: WO2006/19831, 2006, A1. Location in patent: Page/Page column 415
3-bromo-5-nitro-1H-indole Preparation Products And Raw materials
Raw materials5-Nitroindole-->Diethyl bromomalonate-->Pyridinium tribromide-->Pyridine
Tag:3-bromo-5-nitro-1H-indole(525593-33-3) Related Product Information
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