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Basic Information
| CAS No.: | 603-76-9 |
|---|---|
| Name: | 1-Methylindole |
| 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 |
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Synthetic route
Conditions
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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% |
- 180623-97-6
2,3-diiodo-1-methyl-1H-indole
- 603-76-9
1-methylindole
Conditions
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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; |
- 603-76-9
1-methylindole
Conditions
| Conditions | Yield |
|---|---|
| With tris(pentafluorophenyl)borate; water In chloroform at 80℃; for 24h; Sealed tube; | 99% |
Conditions
| Conditions | Yield |
|---|---|
| With cetyltrimethylammonium chloride at 150 - 170℃; under 12001.2 - 24002.4 Torr; Inert atmosphere; Sealed tube; Autoclave; | 98.8% |
Conditions
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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; |
- 590417-55-3
4-bromo-1-methyl-1H-indole
- 603-76-9
1-methylindole
Conditions
| Conditions | Yield |
|---|---|
| With potassium tert-butylate; benzyl alcohol In N,N-dimethyl-formamide at 130℃; for 2.5h; Reagent/catalyst; Schlenk technique; Inert atmosphere; | 96% |
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1-Methylindole
Chemistry
Synonyms of 1-Methylindole(603-76-9): N-METHYLINDOLE;1-Methyl-1H-INDOLE;INDOLE, 1-methyl-;1-METHYLINDOLE (N-);1-METHYLINDOLE;1-METHYLINDOL;1H-INDOLE, 1-methyl-;L-MethylINDOLE
MF: C9H9N
MW: 131.17
EINECS: 210-057-5
BP: 133 °C26 mm Hg
Density : 1.051 g/mL at 20 °C
Refractive Index : n20/D 1.606
FP >230 °C
Storage temp : Refrigerator (+4°C)
Water Solubility : insoluble
Sensitive : Light Sensitive
BRN : 111026
Structural Formula of 1-Methylindole(603-76-9):
MF: C9H9N
MW: 131.17
EINECS: 210-057-5
BP: 133 °C26 mm Hg
Density : 1.051 g/mL at 20 °C
Refractive Index : n20/D 1.606
FP >230 °C
Storage temp : Refrigerator (+4°C)
Water Solubility : insoluble
Sensitive : Light Sensitive
BRN : 111026
Structural Formula of 1-Methylindole(603-76-9):
Toxicity Data With Reference
Hazard Codes : 
Xi
Risk Statements :
R36/37/38: Irritating to eyes, respiratory system and skin
Xi Risk Statements :
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Profile
Specification
Chemical Stability: Light sensitive. Darkens on exposure to light.
Conditions to Avoid: Incompatible materials, light.
Incompatibilities with Other Materials Strong oxidizing agents.
Hazardous Decomposition Products Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization Has not been reported.
Conditions to Avoid: Incompatible materials, light.
Incompatibilities with Other Materials Strong oxidizing agents.
Hazardous Decomposition Products Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization Has not been reported.