| Identification | More | [Name]
3-Bromoindazole | [CAS]
40598-94-5 | [Synonyms]
3-BROMO-1H-INDAZOLE
3-BROMOINDAZOLE
1H-Indazole, 3-bromo-
3-Bromo-1H-indazole ,97% | [Molecular Formula]
C7H5BrN2 | [MDL Number]
MFCD00159926 | [Molecular Weight]
197.03 | [MOL File]
40598-94-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
143-147 °C | [Boiling point ]
333.8±15.0 °C(Predicted) | [density ]
1.770±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
solid | [pka]
11.82±0.40(Predicted) | [Appearance]
White to off-white Solid | [Detection Methods]
HPLC | [CAS DataBase Reference]
40598-94-5(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
3-Bromoindazole was studied in its ability to inhibit blue light-mediated seedling development. Used to study the blue light mechanism and the genetic control of cryptochromes in the growth and development of plant species. | [Synthesis]
General procedure for the synthesis of 3-bromoindazole from indazole: 1H-indazole (3.00 g, 25.4 mmol) was suspended in 2.0 M sodium hydroxide solution (70 mL) at ambient temperature and a solution of bromine (3.00 g, 18.8 mmol) was slowly added. Subsequently, 2.0 M sodium hydroxide solution (30 mL) was added dropwise. The reaction mixture was stirred for 3 h. Sodium bisulfite (0.1 g) was added to quench the reaction, followed by acidification with the addition of 2.0 N hydrochloric acid solution (80 mL). The precipitate was collected by filtration and washed with water to give the final 3-bromoindazole (3.98 g, 80% yield). The product characterization data were as follows: melting point 136 °C; 1H NMR (CDCl3) δ 13.4 (broad single peak, 1H), 7.57 (multiple peaks, 2H), 7.45 (triple peak, 1H), 7.22 (triple peak, 1H); EI-MS (m/z) 198 [M+2]+, 196 [M]+. | [References]
[1] RSC Advances, 2016, vol. 6, # 93, p. 90031 - 90034
[2] Journal of Organic Chemistry, 2018, vol. 83, # 2, p. 930 - 938
[3] Organic Letters, 2015, vol. 17, # 4, p. 1042 - 1045
[4] Patent: US2002/103229, 2002, A1
[5] Patent: US2004/127536, 2004, A1 |
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