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| | 5-METHOXY-1-METHYLINDOLE-3-CARBOXALDEHYDE Basic information |
| Product Name: | 5-METHOXY-1-METHYLINDOLE-3-CARBOXALDEHYDE | | Synonyms: | 3-Formyl-5-methoxy-1-methylindole;5-methoxy-1-methylindole-3-carbaldehyde;3-Formyl-5-methoxy-1-methyl-1H-indole;5-Methoxy-1-methyl-1H-indole-3-carboxaldehyde;5-METHOXY-1-METHYL-1H-INDOLE-3-CARBALDEHYD;5-METHOXY-1-METHYL-1H-INDOLE-3-CARBALDEHYDE;5-METHOXY-1-METHYLINDOLE-3-CARBOXALDEHYDE;AKOS JY2082772 | | CAS: | 39974-94-2 | | MF: | C11H11NO2 | | MW: | 189.21 | | EINECS: | 000-000-0 | | Product Categories: | | | Mol File: | 39974-94-2.mol |  |
| | 5-METHOXY-1-METHYLINDOLE-3-CARBOXALDEHYDE Chemical Properties |
| Melting point | 133-136°C | | Boiling point | 357.9±22.0 °C(Predicted) | | density | 1.14±0.1 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | form | solid | | color | Brown | | Water Solubility | It is insoluble in water. | | Sensitive | Air Sensitive | | BRN | 1528827 | | CAS DataBase Reference | 39974-94-2 |
| Hazard Codes | Xn | | Risk Statements | 36/37/38-22 | | Safety Statements | 26-36 | | HazardClass | IRRITANT | | HS Code | 2933998090 |
| Provider | Language |
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ALFA
| English |
| | 5-METHOXY-1-METHYLINDOLE-3-CARBOXALDEHYDE Usage And Synthesis |
| Uses | 5-Methoxy-1-methylindole-3-carboxaldehyde is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. | | Synthesis | 1. 5-methoxyindole-3-carboxaldehyde (300 mg, 1.71 mmol) was added to a stirring solution of sodium hydride suspension (82 mg, 2.05 mmol, 60% dispersed in mineral oil) in DMF (8 mL) in batches under argon protection, a process which needed to be completed within 5 minutes.
2. The reaction mixture was continued to be stirred for 30 minutes, followed by the addition of iodomethane (0.13 mL, 2.05 mmol) and continued stirring for 1 hour.
3. Upon completion of the reaction, 10% sodium bicarbonate solution (40 mL) was added and the mixture was extracted with ethyl acetate (4×).
4. The organic layers were combined, washed sequentially with 10% sodium bicarbonate solution (2×) and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated.
5. The crude product was purified by column chromatography (eluent: 50:50 ethyl acetate/hexane) to afford 5-methoxy-1-methylindole-3-carbaldehyde (320 mg, 99%) as a light yellow solid.
Rf = 0.35 (50:50 ethyl acetate/hexane); melting point = 130-132°C (literature value: 132-133°C).
1H NMR (CDCl3): δ 9.95 (s, 1H), 7.79 (d, 1H, J = 2.4 Hz), 7.62 (s, 1H), 7.25 (d, 1H, J = 8.8 Hz), 6.96 (dd, 1H, J = 2.4 and 8.9 Hz), 3.90 (s, 3H), 3.85 (s, 3H). | | References | [1] Tetrahedron, 2005, vol. 61, # 7, p. 1793 - 1801
[2] Organic Letters, 2013, vol. 15, # 11, p. 2636 - 2639
[3] Patent: US2003/8850, 2003, A1
[4] Journal of Medicinal Chemistry, 2018, vol. 61, # 14, p. 6261 - 6276
[5] Chemical Biology and Drug Design, 2015, vol. 86, # 4, p. 731 - 745 |
| | 5-METHOXY-1-METHYLINDOLE-3-CARBOXALDEHYDE Preparation Products And Raw materials |
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