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CAS No.: | 603-76-9 |
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Name: | 1-Methylindole |
Article Data: | 287 |
Molecular Structure: | |
Formula: | C9H9N |
Molecular Weight: | 131.177 |
Synonyms: | Indole,1-methyl- (7CI,8CI);1-Methyl-1H-indole;N-Methylindole;NSC212534; |
EINECS: | 210-057-5 |
Density: | 1.008 g/cm3 |
Melting Point: | 94 - 95oC |
Boiling Point: | 239.377 °C at 760 mmHg |
Flash Point: | 98.572 °C |
Solubility: | insoluble in water |
Appearance: | deep yellow viscous liquid with a very unpleasant smell |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 22-24/25-37/39-26 |
PSA: | 4.93000 |
LogP: | 2.17830 |
Conditions | Yield |
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With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; | 99% |
Stage #1: indole With sodium hydride In tetrahydrofuran Inert atmosphere; Stage #2: methyl iodide at 0 - 20℃; for 0.5h; Inert atmosphere; | 99% |
Stage #1: indole With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.25h; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 0.5h; | 99% |
Conditions | Yield |
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With H8O20P8Pt2(4-)*4C34H72N(1+) In methanol Inert atmosphere; Irradiation; | 99% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride In para-xylene at 130℃; for 20h; Catalytic behavior; Temperature; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube; | 99% |
With oxygen In N,N-dimethyl acetamide at 20℃; Schlenk technique; Irradiation; | 95% |
2,3-diiodo-1-methyl-1H-indole
1-methylindole
Conditions | Yield |
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Stage #1: 2,3-diiodo-1-methyl-1H-indole With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.333333h; Stage #2: With ammonium chloride In tetrahydrofuran; water; pentane at -78 - 20℃; | 99% |
Conditions | Yield |
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With potassium hydroxide In acetone | 99% |
Multi-step reaction with 3 steps 1.1: n-BuLi; CO2 / tetrahydrofuran / -78 °C 1.2: t-BuLi / tetrahydrofuran / -78 °C 1.3: 91 percent / ICH2CH2I 2.1: 100 percent / KOH / dimethylformamide 3.1: n-BuLi; ZnCl2 3.2: Pd(PPh3)2Cl2; 2-iodoindole View Scheme | |
Multi-step reaction with 4 steps 1.1: 90 percent 2.1: I2; KOH / dimethylformamide 3.1: n-Bu4NHSO4 / dimethylformamide 4.1: t-BuLi / tetrahydrofuran; pentane / 0.33 h / -78 °C 4.2: 99 percent / NH4Cl / H2O; tetrahydrofuran; pentane / -78 - 20 °C View Scheme |
Conditions | Yield |
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Stage #1: indole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Sealed tube; Stage #2: methyl halide In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Sealed tube; | 99% |
Stage #1: indole With sodium hydroxide In dimethyl sulfoxide Stage #2: methyl halide In dimethyl sulfoxide at 10 - 15℃; for 3h; | |
Stage #1: indole With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 0.5h; Inert atmosphere; Stage #2: methyl halide In N,N-dimethyl-formamide at 0 - 23℃; Inert atmosphere; |
1-methylindole
Conditions | Yield |
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With tris(pentafluorophenyl)borate; water In chloroform at 80℃; for 24h; Sealed tube; | 99% |
Conditions | Yield |
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With cetyltrimethylammonium chloride at 150 - 170℃; under 12001.2 - 24002.4 Torr; Inert atmosphere; Sealed tube; Autoclave; | 98.8% |
Conditions | Yield |
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With potassium carbonate In N,N-dimethyl-formamide at 50 - 130℃; for 9h; | 98% |
With tributyl-amine In N,N-dimethyl-formamide at 285℃; under 112511 Torr; for 0.05h; | 98% |
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 94 - 95℃; for 8h; | 97% |
Conditions | Yield |
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With potassium hydroxide In dimethyl sulfoxide at 20℃; | 97% |
Stage #1: indole With potassium hydroxide In N,N-dimethyl-formamide at 0℃; for 0.333333h; Stage #2: methyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 1h; | |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; | |
Stage #1: indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: methyl bromide In N,N-dimethyl-formamide at 0℃; | |
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; |
4-bromo-1-methyl-1H-indole
1-methylindole
Conditions | Yield |
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With potassium tert-butylate; benzyl alcohol In N,N-dimethyl-formamide at 130℃; for 2.5h; Reagent/catalyst; Schlenk technique; Inert atmosphere; | 96% |