1-Methyl-1H-indazole-3-carbaldehyde

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1-Methyl-1H-indazole-3-carbaldehyde Basic information
Product Name:1-Methyl-1H-indazole-3-carbaldehyde
Synonyms:1-METHYL-1H-INDAZOLE-3-CARBOXALDEHYDE;1-Methyl-1H-indazol-3-carbaldehyde;3-Formyl-1-methyl-1H-indazole;1-Methyl-1H-indazole-3-carboxaldehyde97%;1-Methyl-1H-indazole-3-carboxaldehyde 97%;1H-Indazole-3-carboxaldehyde, 1-methyl-;1-Methylindazole-3-carbaldehyde;1-Methyl-1H-indazole-3-carbaldehyde
CAS:4002-83-9
MF:C9H8N2O
MW:160.17
EINECS:
Product Categories:
Mol File:4002-83-9.mol
1-Methyl-1H-indazole-3-carbaldehyde Structure
1-Methyl-1H-indazole-3-carbaldehyde Chemical Properties
Melting point 61 °C
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
AppearanceLight yellow to yellow Solid
Safety Information
Hazard Codes Xn
Risk Statements 22
HS Code 2933998090
MSDS Information
1-Methyl-1H-indazole-3-carbaldehyde Usage And Synthesis
Synthesis
(1-METHYL-1H-INDAZOL-3-YL)METHANOL

1578-96-7

1-METHYL-1H-INDAZOLE-3-CARBALDEHYDE

4002-83-9

b) Synthesis of 1-methyl-1H-indazole-3-carboxaldehyde: 1-methyl-1H-indazole-3-methanol (0.320 g, 1.97 mmol, prepared from step a) was dissolved in 25 mL of dichloromethane (DCM), followed by the addition of Dess-Martin periodontane (0.920 g, 2.17 mmol). The reaction mixture was stirred at room temperature for 30 minutes. Upon completion of the reaction, 150 mL of diethyl ether was added to dilute, and 50 mL of 2 M sodium hydroxide solution was added to hydrolyze the suspension, and stirring was continued for 10 min. The organic layer was separated, washed sequentially with 1 M sodium hydroxide solution and water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by a pre-populated silica gel column (Isolute, 10 g) with the eluent dichloromethane: methanol (98:2, v/v). The target product 1-methyl-1H-indazole-3-carbaldehyde was obtained in a yield of 0.271 g and 86%. The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 10.21 (s, 1H), 8.29 (m, 1H), 7.50-7.43 (m, 2H), 7.36 (m, 1H), 4.18 (s, 3H).

References[1] Patent: WO2005/66132, 2005, A1. Location in patent: Page/Page column 45-46
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