| Identification | Back Directory | [Name]
3-bromo-5-nitro-1H-indole | [CAS]
525593-33-3 | [Synonyms]
3-Bromo-5-nitroindole
3-bromo-5-nitro-1H-indole
1H-Indole, 3-bromo-5-nitro- | [Molecular Formula]
C8H5BrN2O2 | [MDL Number]
MFCD11110951 | [MOL File]
525593-33-3.mol | [Molecular Weight]
241.04 |
| Chemical Properties | Back Directory | [Melting point ]
191-194 °C | [Boiling point ]
417.6±25.0 °C(Predicted) | [density ]
1.855 | [storage temp. ]
2-8°C | [pka]
13.58±0.30(Predicted) | [Appearance]
White to yellow Solid |
| Hazard Information | Back Directory | [Synthesis]
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 |
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