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[ CAS No. 40598-94-5 ]

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Chemical Structure| 40598-94-5
Chemical Structure| 40598-94-5
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CAS No. :40598-94-5 MDL No. :MFCD00159926
Formula : C7H5BrN2 Boiling Point : 179.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :197.03 g/mol Pubchem ID :721568
Synonyms :

Safety of [ 40598-94-5 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P301+P310-P305+P351+P338 UN#:2811
Hazard Statements:H301-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 40598-94-5 ]

  • Upstream synthesis route of [ 40598-94-5 ]
  • Downstream synthetic route of [ 40598-94-5 ]

[ 40598-94-5 ] Synthesis Path-Upstream   1~11

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YieldReaction ConditionsOperation in experiment
80% With hydrogenchloride; bromine; sodium hydrogensulfite In sodium hydroxide A.
3-Bromo-1H-indazole
To a suspension of 1H-indazole (3.00 g, 25.4 mmol) in 2.0 M sodium hydroxide solution (70 mL) at ambient temperature was added a solution of bromine (3.00 g, 18.8 mmol) in 2.0 M sodium hydroxide solution (30 mL) dropwise.
After stirring for 3 hours, to the reaction mixture was added sodium bisulfite (0.1 g), followed by 2.0 N hydrochloric acid solution (80 mL).
The precipitates were filtered and washed with water to provide the title compound (3.98 g, 80percent yield): mp 136° C.; 1H NMR (CDCl3) δ 13.4 (br s, 1H), 7.57 (m, 2H), 7.45 (t, 1H), 7.22 (t, 1H); EI-MS (m/z) 198 [M+2]+, 196 [M]+.
80% at 20℃; for 3 h; Bromine (1.5g, 9.4mmol) in 2M NaOH solution (lOmL) was added drop wise tosuspension of indazole (1.5g, 12.7mmol) in 2M NaOH solution (23mL) at ambient temperature. Stined the reaction mass for 3h at room temperature and added sodium bisulfate (0.05g) followed by the addition of 2N HC1. The solid precipitated was filtered out and washed with water, suction dried followed by in Rotavap under reduced pressure to afford the title compound (2g, 80percent). LCMS: mlz = 197.1 (M+H).
45% With bromine; sodium hydrogensulfite In sodium hydroxide 3-Bromoindazole 4a was prepared using a procedure described by Boulton, B. E. and Coller, A. W (Aust. J Chem., 1974, 27, 2343-2346):
A solution of bromine (0.99 g, 6.19 mmol) in 10percent NaOH was slowly added to a suspension of indazole (1 g, 8.50 mmol) in 2 N NaOH (25 mL).
The reaction mixture became a thick white slurry.
After stirring for 2 hours, a small amount of sodium bisulfite was added and the solution was neutralized with 1 N HCl.
The white solid was filtered and washed with water.
Recrystallization from water gave 0.76 g (45percent yield) of 3-bromoindazole 4a:
1H NMR (CDCl3) δ 7.22-7.27 (m, 1H), 7.43-7.52 (m, 2H), 7.60-7.67 (m, 1H);
IR (KBr, cm-1) 3154, 2944, 2915, 1624, 1479, 1331, 1242, 1026, 901, 770, 735, 639;
MS m/e 195 (MH-);
Anal. Calcd for C7H5BrN2: C, 42.67; H, 2.56; N, 14.22 Found: C, 42.37; H, 2.55; N, 14.06.
Reference: [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,
[6] Patent: US2005/9876, 2005, A1,
[7] Patent: WO2016/193939, 2016, A1, . Location in patent: Page/Page column 84
[8] Synthesis, 2011, # 16, p. 2651 - 2663
[9] Patent: US2002/99208, 2002, A1,
[10] Journal fuer Praktische Chemie (Leipzig), 1924, vol. <2> 108, p. 314
[11] Patent: WO2006/50006, 2006, A2, . Location in patent: Page/Page column 47-48
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Reference: [1] Chemische Berichte, 1899, vol. 32, p. 1799[2] Justus Liebigs Annalen der Chemie, 1899, vol. 305, p. 354 Anm. 10
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Reference: [1] Chemische Berichte, 1899, vol. 32, p. 1781
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Reference: [1] Patent: US2002/99208, 2002, A1,
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Reference: [1] Synthesis, 1992, # 10, p. 937 - 939
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Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1141,1157
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Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1141,1157
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Reference: [1] Chemische Berichte, 1899, vol. 32, p. 1781
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Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1141,1157
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Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1141,1157
[2] Chemische Berichte, 1922, vol. 55, p. 1141,1157
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  • [ 130641-38-2 ]
Reference: [1] Patent: WO2011/15501, 2011, A1,
[2] Patent: WO2011/15502, 2011, A1,
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