3-Bromo-5-chloro-1H-indazole

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3-Bromo-5-chloro-1H-indazole Basic information
Product Name:3-Bromo-5-chloro-1H-indazole
Synonyms:3-BROMO-5-CHLORO (1H)INDAZOLE;1H-Indazole, 3-bromo-5-chloro-
CAS:885521-43-7
MF:C7H4BrClN2
MW:231.48
EINECS:
Product Categories:
Mol File:885521-43-7.mol
3-Bromo-5-chloro-1H-indazole Structure
3-Bromo-5-chloro-1H-indazole Chemical Properties
density 1.878
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
AppearanceLight yellow to yellow Solid
Safety Information
HazardClass IRRITANT
MSDS Information
3-Bromo-5-chloro-1H-indazole Usage And Synthesis
Synthesis
5-CHLORO (1H)INDAZOLE

698-26-0

3-Bromo-5-chloro-1H-indazole

885521-43-7

General procedure for the synthesis of 3-bromo-5-chloro-1H-indazole from 5-chloro-1H-indazole: 5-chloro-1H-indazole (2.5 g, 16.1 mmol) was dissolved in dichloromethane (150 mL) and N-bromosuccinimide (2.9 g, 16.6 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure and the residue was dissolved in ethyl acetate (100 mL) and washed sequentially with water (50 mL) and saturated saline (50 mL). The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 3-bromo-5-chloro-1H-indazole (3.7 g, 94% yield) as a brown solid. The product was confirmed by 1H NMR (DMSO-d6, 400MHz): δ 13.63 (s, 1H), 7.67-7.59 (m, 2H), 7.49-7.44 (m, 1H).TLC analytical conditions: 50% ethyl acetate/heptane (Rf = 0.43).

References[1] Patent: WO2017/31325, 2017, A1. Location in patent: Paragraph 0764
[2] Synthesis, 2011, # 16, p. 2651 - 2663
[3] Patent: US2013/281433, 2013, A1. Location in patent: Paragraph 1088
3-Bromo-5-chloro-1H-indazole Preparation Products And Raw materials
Raw materials5-CHLORO (1H)INDAZOLE-->Dichloromethane-->N-Bromosuccinimide
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