3-Methyl-6-nitro-1H-indazole
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3-Methyl-6-nitro-1H-indazole
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CAS No:
6494-19-5
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Formula:
C8H7N3O2
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Chemical Name:
3-Methyl-6-nitro-1H-indazole
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Synonyms:
1H-Indazole,3-methyl-6-nitro-;3-Methyl-6-nitro-1H-indazole;3-Methyl-6-nitroindazole;6-Nitro-3-methylindazole
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CAS No:
Safety Information
24/25-36/37
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P501
H302+H312+H332
|Warning|H302+H312+H332 (100%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 2 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
3-Methyl-6-nitro-1H-indazole Use and Manufacturing
Intermediate A solution of tert-butyl nitrite (12.5ml, 0.075mol) in glacial aceticacid (50ml) was added dropwise to a 2-1 (12.5g, 0.075mol) in glacial aceticacid (375mL) solution. Continue stirring the reaction 30min. The reactionsolution was concentrated to dryness, the resulting orange solid was dissolvedin ethyl acetate (150 mL), and saturated aqueous sodium bicarbonate (125mL ×3), dried, filtered, and concentrated to give 13.0 g of a yellow solid, yield98percent, Step 1 To a solution of Second Step [Show Image] To an ethyl acetate solution (50 mL) of the product (1.17 g, 6.60 mmol) of the first step, 10percent Pd-C (0.46 g) was added, followed by stirring under a hydrogen gas flow at room temperature for 10 hours. The insoluble substances were filtered through cerite and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:n-hexane = 3:1) to obtain 0.57 g of 6-amino-3-methylindazole. 1H-NMR (CDCl3) d: 2.50 (s, 3H), 6.4-6.65 (m, 2H), 7.43 (d, 1H, J = 8.4 Hz), 9.35 (br, 1H).
3-Methyl-6-nitroindazole a reactant used in the preparation of Pazopanib (P210925), an oral angiogenesis inhibitor targeting VEGFR and PDGFR.
Computed Properties
Molecular Weight:177.16
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:177.053826475
Monoisotopic Mass:177.053826475
Topological Polar Surface Area:74.5
Heavy Atom Count:13
Complexity:216
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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