4-METHYL(1H)INDAZOLE
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4-METHYL(1H)INDAZOLE
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CAS No:
3176-63-4
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Formula:
C8H8N2
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Chemical Name:
4-METHYL(1H)INDAZOLE
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Synonyms:
4-METHYLINDAZOLE;4-METHYL(1H)INDAZOLE;1H-Indazole,4-methyl-;4-methyl-1H-indazole(SALTDATA:FREE)
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CAS No:
Safety Information
Xn
P264, P270, P301+P312, P330, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4-METHYL(1H)INDAZOLE Use and Manufacturing
2-Methyl-4-[1-(4-trifluoromethylphenyl)-1H-indazol-4-ylmelthylsulfanyl]phenoxyacetic; Step A; 4-Methyl-lH-indazole; Add tert-butyl nitrite (30 mL, 248 mmol) to a solution of commercially available 2, 3-dimethylaniline (20 mL, 165 mmol) in chloroform (600 mL) at room temperature under nitrogen, stir the mixture for 15 min and add 18-crown-6 (4.3 g, 16.5 mmol) and potassium acetate (32 g, 333 mmol). Stir the mixture for 45 min and then heat at reflux for 1 h. Add additional tert-butyl nitrite (10 mL, 82 mmol) and heat the mixture at reflux for an additional 1 h. Remove the solids from the cooled mixture and wash with chloroform (3 x 200 mL). Wash the filtrate washed with water (400 mL), dry over MgS04, remove the solvents under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (9: 1), to afford 4-methyl-lH-indazole as an off-white solid (5.4 g, 25percent) : lH NMR (CDC13) 8 2.70 (s, 3H), 6.90 (d, 1H), 7.50 (m, 2H), 8.10 (s, 1H).2-Methyl-4-[1-(4-trifluoromethylphenyl)-1H-indazol-4-ylmelthylsulfanyl]phenoxyacetic; Step A; 4-Methyl-lH-indazole; Add tert-butyl nitrite (30 mL, 248 mmol) to a solution of commercially available 2, 3-dimethylaniline (20 mL, 165 mmol) in chloroform (600 mL) at room temperature under nitrogen, stir the mixture for 15 min and add 18-crown-6 (4.3 g, 16.5 mmol) and potassium acetate (32 g, 333 mmol). Stir the mixture for 45 min and then heat at reflux for 1 h. Add additional tert-butyl nitrite (10 mL, 82 mmol) and heat the mixture at reflux for an additional 1 h. Remove the solids from the cooled mixture and wash with chloroform (3 x 200 mL). Wash the filtrate washed with water (400 mL), dry over MgS04, remove the solvents under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (9: 1), to afford 4-methyl-lH-indazole as an off-white solid (5.4 g, 25%) : lH NMR (CDC13) 8 2.70 (s, 3H), 6.90 (d, 1H), 7.50 (m, 2H), 8.10 (s, 1H).