1-Methylindole supplier | CasNO.603-76-9

Name
1-Methylindole
EINECS 210-057-5
CAS No. 603-76-9
Article Data287
CAS DataBase
Density 1.008 g/cm³
Solubility insoluble in water
Melting Point 94 - 95oC
Formula C₉H₉N
Boiling Point 239.377 °C at 760 mmHg
Molecular Weight 131.177
Flash Point 98.572 °C
Transport Information
Appearance deep yellow viscous liquid with a very unpleasant smell
Safety 22-24/25-37/39-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Indole,1-methyl- (7CI,8CI);1-Methyl-1H-indole;N-Methylindole;NSC212534;
PSA 4.93000
LogP 2.17830

Synthetic route

: 120-72-9
indole

: 74-88-4
methyl iodide

: 603-76-9
1-methylindole

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%

: 824-21-5
N-methylindoline

: 603-76-9
1-methylindole

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%

: 120-72-9
indole

MeX: MeX

: 603-76-9
1-methylindole

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

: 120-72-9
indole

methyl halide: methyl halide

: 603-76-9
1-methylindole

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;

: 1-methyl-1H-indole-2,3,5,7-d4

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
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

Conditions	Yield
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

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%

: 120-72-9
indole

: 74-83-9
methyl bromide

: 603-76-9
1-methylindole

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%

: 40899-71-6
1-benzenesulfonylindole

: 865-33-8
potassium methanolate

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 4h; Sealed tube; Glovebox;	96%
In acetonitrile at 20℃;	96%

: 112398-75-1
5-chloro-1-methyl-1H-indole

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
With potassium tert-butylate; N,N-dimethyl-formamide In dimethyl sulfoxide at 35℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;	96%

: 120-72-9
indole

: 77-78-1
dimethyl sulfate

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
With potassium tert-butylate In acetone at 20℃; for 1h;	94%
With potassium hydroxide In acetone Methylation;	93%
With sodium amide; toluene
With potassium carbonate

: 5339-28-6
N-methyl-N-(2-vinylphenyl)amine

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
With p-benzoquinone; lithium chloride; dichloro bis(acetonitrile) palladium(II) In tetrahydrofuran for 18h; Heating;	94%

: 19012-03-4
N-methyl-3-formylindole

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
With palladium nanoparticles supported on fibrous silica In cyclohexane at 130℃; for 22h; Molecular sieve;	94%

: 61-70-1
N-methyl-2-indolinone

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
With dimethylethylsilane; 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; bis(pentafluorophenyl)borohydride In dichloromethane; toluene at 20℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;	94%

: 81471-20-7
3-bromo-1-methyl-1H-indole

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
With sodium tetrahydroborate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 20℃; for 19h; Reagent/catalyst; Time; Inert atmosphere;	93%
With di-tert-butyl peroxide; caesium carbonate; isopropyl alcohol at 120℃; for 24h; Inert atmosphere;	90 %Chromat.

: 81471-20-7
3-bromo-1-methyl-1H-indole

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 19h; Inert atmosphere;	93%

: 280563-07-7
1-methyl-5-iodoindole

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
With potassium tert-butylate; benzyl alcohol In N,N-dimethyl-formamide at 90℃; for 2h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	92%
With potassium tert-butylate; benzaldehyde In N,N-dimethyl-formamide at 90℃; for 2h; Schlenk technique; Inert atmosphere;	86%
With 1,3-bis(2,6-diisopropylphenyl)-2,4-diphenylimidazole In N,N-dimethyl-formamide at 20℃; for 36h; Glovebox;	85%
With 2-(2-methoxyethoxy)ethyl alcohol; oxygen; sodium hydride In 1,4-dioxane at 20℃; for 24h; Schlenk technique; chemoselective reaction;	76%

: 10075-52-2
5-bromo-1-methyl-H-indole

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
With 1,1,1,2,2,2-hexamethyldisilane; potassium methanolate; acetonitrile at 25℃; for 5h; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube;	92%
With 2-H-1,3-di-tert-butyl-1,3,2-diazaphosphorinane; 2,2'-azobis(isobutyronitrile) In toluene at 90℃; for 12h;	70%
With tributyl-amine; tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 1.8h; Inert atmosphere; Electrolysis;	64%

: 31271-90-6
1-(p-toluenesulfonyl)-1H-indole

: 865-33-8
potassium methanolate

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 4h; Solvent; Sealed tube; Glovebox;	92%
In acetonitrile at 20℃; Solvent;	95 %Chromat.

: 32387-21-6
1-methyl-3-indolecarboxylic acid

: 91-01-0
1,1-Diphenylmethanol

A: 53924-28-0
3-(1,1-diphenylmethyl)-1-methyl-1H-indole

B: 603-76-9
1-methylindole

Conditions

Conditions	Yield
With sodium tetrachloroaurate(III) dihyrate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 16h; Reagent/catalyst; Solvent; Sealed tube;	A 91% B 9%
With sodium tetrachloroaurate(III) dihyrate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 16h; Reagent/catalyst; Solvent; Sealed tube;	A 5% B 47%
With sodium tetrachloroaurate(III) dihyrate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 16h; Reagent/catalyst; Solvent; Sealed tube;	A 47% B 5%

...Expand

: 120-72-9
indole

methy halide: methy halide

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
Stage #1: indole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: methy halide at 0 - 20℃; for 24h;	90%

: 120-72-9
indole

: 373-68-2
tetramethylammonium fluoride

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
In toluene at 100℃; for 3h;	90%

: 219605-52-4
2′-N,N-dimethylaminophenylacetylene

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
With ethanol at 120℃; for 4h; Microwave irradiation; Inert atmosphere; Green chemistry;	89%

: 553-90-2
Dimethyl oxalate

: 120-72-9
indole

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide for 0.166667h; Heating;	88%
With potassium tert-butylate In N,N-dimethyl-formamide for 0.25h; Heating;	88%

: 120-72-9
indole

: 431-47-0
trifluoroacetic acid-methyl ester

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
Stage #1: indole With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: trifluoroacetic acid-methyl ester In N,N-dimethyl-formamide for 10h;	88%

: 89246-30-0
2-bromo-1-methyl-1H-indole

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 0.8h; Reagent/catalyst; Inert atmosphere;	87%

: 496-15-1
1-indoline

: 603-76-9
1-methylindole

Conditions

Conditions	Yield
With copper(II) choride dihydrate; oxygen In dimethyl sulfoxide at 20 - 120℃; for 0.166667h;	87%
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran; mineral oil / 24 h / 20 °C 2: tris(pentafluorophenyl)borate / para-xylene / 22 h / 150 °C / Inert atmosphere; Sealed tube View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dimethyl sulfoxide / 20 h / 150 °C / Sealed tube; Schlenk technique; Inert atmosphere 2: sodium carbonate / ethyl acetate / 24 h / 120 °C / Sealed tube; Green chemistry View Scheme
Multi-step reaction with 2 steps 1: acetic acid; sodium cyanoborohydride / water; methanol / 1 h / 20 °C 2: dichloro[1,3-bis(2-methylphenyl)-2-imidazolidinylidene](benzylidene) (tricyclohexylphosphine) ruthenium(II); oxygen / ethyl acetate / 46 h / 70 °C / 760.05 Torr / Sealed tube View Scheme

: 603-76-9
1-methylindole

: 1113-69-5
1,1-dicyano-2,2-bis(trifluoromethyl)ethene

: 2-[2,2,2-Trifluoro-1-(1-methyl-1H-indol-3-yl)-1-trifluoromethyl-ethyl]-malononitrile

Conditions

Conditions	Yield
	100%

: 603-76-9
1-methylindole

: 122-51-0
orthoformic acid triethyl ester

: 27065-95-8
tri(1-methyl-1H-indole-3-yl)methane

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol at 70℃; for 0.166667h;	100%
With iodine In acetonitrile at 20℃; for 0.133333h;	90%
With acid-washed montmorillonite K10 clay at 20℃;	87%
With acid-washed montmorillonite K10 clay (acid-clay) at 20℃;

: 603-76-9
1-methylindole

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 61995-39-9
4,5-Dichloro-3-hydroxy-1-(1-methyl-1H-indol-3-yl)-6-oxo-cyclohexa-2,4-diene-1,2-dicarbonitrile

Conditions

Conditions	Yield
In 1,4-dioxane for 24h; Ambient temperature;	100%

: 603-76-9
1-methylindole

: 85092-84-8
3-iodo-1-methyl-1H-indole

Conditions

Conditions	Yield
With N-iodo-succinimide In N,N-dimethyl-formamide at 0℃; for 1.5h; Inert atmosphere;	100%
With potassium hydroxide; iodine In N,N-dimethyl-formamide Ambient temperature;	98%
With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique; Glovebox;	97%

: 603-76-9
1-methylindole

: 5153-67-3
nitrostyrene

: 109811-96-3
1-methyl-3-(2-nitro-1-phenylethyl)-1H-indole

Conditions

Conditions	Yield
With Zn(2+)*2C6H6NO2S2(1-) In ethanol at 20℃; for 24h;	100%
With 1H-pyrrolo[2,3-b]pyridinium substituted-borate salt In toluene at 0 - 20℃; for 24h;	99%
Stage #1: nitrostyrene With (S)-10,10'-bis[(S)-4-isopropyl-4,5-dihydrooxazol-2-yl]-9,9'-biphenanthrene; zinc(II) trifluoroacetate In diethyl ether at 20℃; for 0.25h; Inert atmosphere; Stage #2: 1-methylindole In diethyl ether at 20℃; Friedel-Crafts alkylation; Inert atmosphere;	99%

: 603-76-9
1-methylindole

: 78-94-4
methyl vinyl ketone

: 91956-43-3
4-(1-methyl-1H-indol-3-yl)-butan-2-one

Conditions

Conditions	Yield
With trityl tetrafluoroborate In dichloromethane Inert atmosphere;	100%
With rac-9-phenyl-9H-cyclopenta[1,2-c:4,3-c']diphenanthren-9-ylium tetrakis(3,5-bis(tri-fluoromethyl)phenyl)borate In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation; Glovebox; Inert atmosphere;	100%
hafnium tetrachloride In acetonitrile at 20℃; for 0.333333h;	99%

: 603-76-9
1-methylindole

: 104-88-1
4-chlorobenzaldehyde

: 3-[(4-chlorophenyl)(1-methyl-1H-indol-3-yl)methyl]-1-methyl-1H-indole

Conditions

Conditions	Yield
With o-benzenedisulfonimide at 20℃; for 0.0833333h; Friedel Crafts alkylation; neat (no solvent);	100%
With cellulose sulfuric acid at 50℃; for 0.333333h; Neat (no solvent); Grinding; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction;	98%
With N-Bromosuccinimide at 20℃; for 6h;	96%

: 603-76-9
1-methylindole

: 62668-02-4
(E)-1,3-diphenyl-2-propen-1-ol

: 3-((E)-1,3-diphenyl-2-propenyl)-1-methyl-1H-indole

Conditions

Conditions	Yield
With 5,11,17,23-tetrasulfonate-25,26,27,28-tetrakis(propoxy)calix[4]arene tetrasodium salt In water at 50℃; for 61h; Reagent/catalyst; Concentration; Time; Green chemistry;	100%
With magnetic Fe3O4-grafted calix[6]arene sulfonic acid In water at 50℃; for 24h; Catalytic behavior; Reagent/catalyst;	99.9%
With zinc dibromide In neat (no solvent) for 1.5h; Milling; Green chemistry; chemoselective reaction;	92%

: 603-76-9
1-methylindole

: 728-87-0
4,4'-Dimethoxybenzhydrol

: 3-[bis(4-methoxyphenyl)methyl]-1-methyl-1H-indole

Conditions

Conditions	Yield
With 5,11,17,23-tetrasulfonate-25,26,27,28-tetrakis(propoxy)calix[4]arene tetrasodium salt In water at 50℃; for 24h; Reagent/catalyst; Concentration; Green chemistry;	100%
With magnetic Fe3O4-grafted calix[4]arene sulfonic acid In water at 50℃; for 25h; Catalytic behavior; Reagent/catalyst;	99.9%
With sodium tetrachloroaurate(III) dihydrate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 80℃; for 16h; Sealed tube;	95%
With o-benzenedisulfonimide In neat (no solvent) at 20℃; for 0.25h; Friedel-Crafts Alkylation;	94%
With dodecylbenzene-sulphonic acid In water at 80℃; for 24h; Friedel-Crafts reaction;	92%

: 603-76-9
1-methylindole

: 918108-96-0
thuriferic acid methyl ester

: 1032712-17-6
C32H31NO8

Conditions

Conditions	Yield
With indium(III) bromide In dichloromethane at 20℃; for 2h; Michael addition; diastereoselective reaction;	100%

: 603-76-9
1-methylindole

: C10H6(N(CH3)2)2(BC8H14)(1+)*N(SO2CF3)2(1-)=(C10H6(N(CH3)2)2(BC8H14))N(SO2CF3)2

A: 1283232-87-0
3-(9-borabicyclo[3.3.1]nonan-9-yl)-1-methyl-1H-indole

B: C2HF6NO4S2*C14H18N2

Conditions

Conditions	Yield
In dichloromethane at 50℃; for 2h; Sealed vessel; Inert atmosphere;	A 100% B n/a

...Expand

: 603-76-9
1-methylindole

: 3140-75-8
4,4′,4″‑[(1,3,5‑triazine‑2,4,6‑triyl)tris(oxy)]tribenzaldehyde

: 1431159-05-5
C78H63N9O3

Conditions

Conditions	Yield
With silica sulfuric acid In acetonitrile at 20℃; for 0.5h; Friedel-Crafts Alkylation;	100%

: 860772-38-9
(E)‐1‐(1‐methyl‐1H‐imidazole‐2‐yl)‐but‐2‐en‐1‐one

: 603-76-9
1-methylindole

: 1-(1-methyl-1H-imidazol-2-yl)-3-(1-methyl-1H-indol-3-yl)butan-1-one

Conditions

Conditions	Yield
With [ZnIIYIII(N,N'-bis(3-methoxysalicylidene)cyclohexane-1,2-diamine)(NO3)2(o-vanillin)2(MeOH)](MeOH) In ethyl acetate at 20℃; for 72h; Friedel-Crafts Alkylation; Inert atmosphere;	100%
With copper(II) nitrate trihydrate In aq. buffer at 20℃; for 72h; pH=6.5; Friedel-Crafts Alkylation;	88%
With copper(II) nitrate trihydrate In aq. buffer at 20℃; for 72h; pH=6.5; Reagent/catalyst; Friedel-Crafts Alkylation; enantioselective reaction;	88%
With 4,4'-dimethyl-2,2'-bipyridines; copper(II) nitrate trihydrate In acetonitrile at 20℃; for 72h; Catalytic behavior; Reagent/catalyst; Friedel-Crafts Alkylation; Inert atmosphere;	80%
With copper(II) nitrate trihydrate In acetonitrile at 20℃; for 16h; pH=7; Friedel-Crafts Alkylation;

: 603-76-9
1-methylindole

: 23949-31-7
1-(2,4-dimethoxy-phenyl)-1,3-dihydro-isobenzofuran

: C25H25NO3

Conditions

Conditions	Yield
With iron(III) chloride In 1,4-dioxane at 20℃; for 6h;	100%

: 603-76-9
1-methylindole

: 1,1'-dimethyl-2',3'-dihydro-1H,1'H-2,3'-biindole

Conditions

Conditions	Yield
With dimethylaluminum chloride In hexane; toluene at -30℃; for 18h; Temperature;	100%

: 603-76-9
1-methylindole

: 1631-33-0
Et3SiD

: 1-methyl-1H-indole-2,3-d2

Conditions

Conditions	Yield
With norborn-2-ene; carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In toluene at 150℃; for 16h; Inert atmosphere;	100%

: 868765-12-2
2-phenylethynyl-quinoline-3-carbaldehyde

: 603-76-9
1-methylindole

: 1-(1-methyl-1H-indol-3-yl)-3-phenyl-1H-pyrano[4,3-b]quinoline

Conditions

Conditions	Yield
With silver trifluoromethanesulfonate In 1,2-dichloro-ethane for 1 - 24h; Inert atmosphere; Reflux;	100%

: 603-76-9
1-methylindole

: 1421925-29-2
7-chloro-2-(phenylethynyl)quinoline-3-carbaldehyde

: 7-chloro-1-(1-methyl-1H-indol-3-yl)-3-phenyl-1H-pyrano[4,3-b]quinoline

Conditions

Conditions	Yield
With silver trifluoromethanesulfonate In 1,2-dichloro-ethane for 1 - 24h; Inert atmosphere; Reflux;	100%

: 603-76-9
1-methylindole

: 1170697-31-0
1-methyl-3-propyl-1H-indole

: 2-(1’-methylindol-3’-yl)-1-methyl-3-propylindole

Conditions

Conditions	Yield
Stage #1: 1-methyl-3-propyl-1H-indole With 2,6-di-tert-butyl-pyridine; trifluoromethylsulfonic anhydride; dimethyl sulfoxide In dichloromethane; dimethyl sulfoxide at -78℃; for 0.25h; Inert atmosphere; Stage #2: 1-methylindole In dichloromethane; dimethyl sulfoxide for 0.25h; Inert atmosphere;	100%

: 603-76-9
1-methylindole

: 1263090-20-5
1-benzyl-7-(trifluoromethyl)indoline-2,3-dione

: C25H19F3N2O2

Conditions

Conditions	Yield
With C24H30N8; scandium tris(trifluoromethanesulfonate) In acetonitrile at 20℃; for 18h; Friedel-Crafts Alkylation; Inert atmosphere; Molecular sieve; chemoselective reaction;	100%

: 603-76-9
1-methylindole

: 706-08-1, 5153-69-5
trans-1-(4-fluorophenyl)-2-nitro-ethene

: 1430076-20-2
3-(1-(4-fluorophenyl)-2-nitroethyl)-1-methyl-1H-indole

Conditions

Conditions	Yield
With Zn(2+)*2C6H6NO2S2(1-) In ethanol at 20℃; for 24h;	100%
With C22H35N4S(1+)*BF4(1-) In dichloromethane at 20℃; for 44h; Friedel-Crafts Alkylation; Inert atmosphere;	92%
With rose bengal In water at 60℃; Friedel-Crafts Alkylation; Irradiation;	81%
With 2C32H12BF24(1-)*C13H16N4S(2+) In chloroform-d1 at 20℃; Inert atmosphere;

: 603-76-9
1-methylindole

: C19H16BF3NO(1-)

: ((4R*,6R*)-6-(1-methyl-1H-indol-3-yl)-4-(o-tolyl)-1,4,5,6-tetrahydropyridin-3-yl)(phenyl)methanone

Conditions

Conditions	Yield
With trifluoroacetic acid In tetrahydrofuran; methanol at 20℃; diastereoselective reaction;	100%

: 603-76-9
1-methylindole

: 87-42-3
6-chloro-7H-purine

: 6-(1-methyl-1H-indol-3-yl)-7H-purine

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid; 1,1,1,3',3',3'-hexafluoro-propanol at 60℃; for 24h; Reagent/catalyst;	100%

: 603-76-9
1-methylindole

: 50-00-0
formaldehyd

: 124-40-3
dimethyl amine

: 52972-61-9
3-(N,N-dimethylaminomethyl)-1-methylindole

Conditions

Conditions	Yield
Stage #1: 1-methylindole; formaldehyd; dimethyl amine With acetic acid In water at 0 - 50℃; Mannich reaction; Stage #2: With sodium hydroxide In water	99%
With acetic acid at 0 - 50℃; for 14h;	91%
With zinc(II) chloride In ethanol at 20℃; for 2.5h; Mannich reaction;	82%

...Expand

: 603-76-9
1-methylindole

: 2058-74-4
1-methyl-1H-indole-2,3-dione

: 75833-69-1
1-methyl-3,3-bis(1-methyl-1H-indol-3-yl)-2,3-dihydro-1H-indol-2-one

Conditions

Conditions	Yield
With C19H22N4; scandium tris(trifluoromethanesulfonate) In acetonitrile at 20℃; for 18h; Friedel-Crafts Alkylation; Inert atmosphere; Molecular sieve; chemoselective reaction;	99%
In acetic acid at 35℃; for 24h;	92%
With H6P2W18O62 In water at 60℃; for 0.5h;	90%

: 603-76-9
1-methylindole

: 950-81-2
4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one

: <4-Antipyryl-><1-methyl-3-indolyl->carbenium-tetrafluoroborate

Conditions

Conditions	Yield
With tetrafluoroboric acid In diethyl ether; dichloromethane for 0.5h;	99%

: 603-76-9
1-methylindole

: 13887-54-2
methyl 2-methoxy-2-(piperidin-1-yl)acetate

: methyl 2-(1-methyl-1H-indol-3-yl)-2-(piperidin-1-yl)acetate

Conditions

Conditions	Yield
With hafnium tetrakis(trifluoromethanesulfonate); chloro-trimethyl-silane In dichloromethane at 20℃; for 1h;	99%
With Methyltrichlorosilane In acetonitrile for 39h; Ambient temperature;	88%

: 603-76-9
1-methylindole

: 1147550-11-5
ammonium thiocyanate

: 23518-17-4
N-methyl-3-thiocyanato-1H-indole

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate In methanol Ambient temperature;	99%
In acetonitrile at 20℃; for 3h; Electrochemical reaction; Inert atmosphere;	99%
With oxygen In tetrahydrofuran at 25℃; under 750.075 Torr; for 10h; Irradiation;	98%

1-Methylindole Chemical Properties

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):

1-Methylindole Toxicity Data With Reference

Hazard Codes :

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

1-Methylindole 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

1-Methylindole 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.

Product Name

1-Methylindole

Synthetic route

1-Methylindole Chemical Properties

1-Methylindole Toxicity Data With Reference

1-Methylindole Safety Profile

1-Methylindole Specification

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