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603-76-9

Basic Information
CAS No.: 603-76-9
Name: 1-Methylindole
Article Data: 287
Molecular Structure:
Molecular Structure of 603-76-9 (1-Methylindole)
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: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-37/39-26
PSA: 4.93000
LogP: 2.17830
Synthetic route
120-72-9

indole

74-88-4

methyl iodide

603-76-9

1-methylindole

Conditions
ConditionsYield
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%
824-21-5

N-methylindoline

603-76-9

1-methylindole

Conditions
ConditionsYield
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
ConditionsYield
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%
120-72-9

indole

MeX

MeX

603-76-9

1-methylindole

Conditions
ConditionsYield
With potassium hydroxide In acetone99%
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
120-72-9

indole

methyl halide

methyl halide

603-76-9

1-methylindole

Conditions
ConditionsYield
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-methyl-1H-indole-2,3,5,7-d4

603-76-9

1-methylindole

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate; water In chloroform at 80℃; for 24h; Sealed tube;99%
271-26-1

3H-indole

616-38-6

carbonic acid dimethyl ester

603-76-9

1-methylindole

Conditions
ConditionsYield
With cetyltrimethylammonium chloride at 150 - 170℃; under 12001.2 - 24002.4 Torr; Inert atmosphere; Sealed tube; Autoclave;98.8%
120-72-9

indole

616-38-6

carbonic acid dimethyl ester

603-76-9

1-methylindole

Conditions
ConditionsYield
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%
120-72-9

indole

74-83-9

methyl bromide

603-76-9

1-methylindole

Conditions
ConditionsYield
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
ConditionsYield
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 Product Name: 1-Methylindole Molecular Weight: 131.17 CAS NO: 603-76-9 EC NO: 210-057-5 Molecular Formula: C9H9N

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    1-Methylindole CAS NO.603-76-9

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    Product name: 1-Methylindole CAS No.: 603-76-9 Molecule Formula:C9H9N Molecule Weight:131.17 Purity: 98.0% Package: 200kg/drum Description:Light yellow oil-like liquid Manufacture Standards:Enterprise Standard TEST

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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):

Toxicity Data With Reference

Hazard Codes :   Xi
Risk Statements :
R36/37/38:  Irritating to eyes, respiratory system and skin   

Safety Profile

Safety Statements :
S22:  Do not breathe dust 
S24/25:  Avoid contact with skin and eyes 
S37/39:  Wear suitable gloves and eye/face protection 
S26:  In case of contact with eyes, rinse immediately with plenty of WATER and seek medical advice 

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.