5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With potassium hydroxide In methanol for 1h; Reflux; | 100% |
With potassium hydroxide In methanol for 1h; Reflux; Large scale; | 98% |
bromure d'acetylamino-2 methoxy-5 benzyltriphenylphosphonium
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With potassium tert-butylate In toluene for 0.25h; Heating; | 97% |
5-methoxy-2-methyl-3-(phenylthio)-1H-indole
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With thiosalicilyc acid In trifluoroacetic acid for 1.5h; Ambient temperature; | 96% |
4-methoxy-2-(prop-1-yn-1-yl)aniline
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With Pd(II)-Y zeolites In toluene at 110℃; for 20h; Catalytic behavior; | 96% |
With palladium dichloride In acetonitrile at 85℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With acetic acid for 8h; Reagent/catalyst; Reflux; Large scale; | 94% |
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran; ethanol for 6h; Reflux; | 92% |
With ethanol; potassium hydroxide In tetrahydrofuran Reflux; |
(3-Chloro-4-methoxy-phenyl)-isopropylidene-amine
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With sodium amide; sodium t-butanolate In tetrahydrofuran at 20℃; for 24h; | 87% |
Conditions | Yield |
---|---|
With oxygen; palladium diacetate; acetic acid In dimethyl sulfoxide at 70℃; under 760.051 Torr; for 18h; Schlenk technique; Molecular sieve; | 79% |
With oxygen; palladium diacetate; acetic acid In dimethyl sulfoxide at 70℃; for 18h; Schlenk technique; Molecular sieve; | 79% |
With copper diacetate; palladium diacetate In dimethyl sulfoxide at 40℃; for 24h; Inert atmosphere; | 55% |
N-(4-methoxyphenyl)-1-methylethenesulfinamide
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at -30℃; for 4h; | 75% |
2-methyl-3-methylthio-5-methoxy-1H-indole
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
aluminum nickel | 72% |
5-methoxy-2-nitro-benzaldehyde
tert-butyl 2-(triphenylphosphoranylidene)propionate
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With triphenylphosphine In diphenylether at 260℃; for 1h; | 48% |
N,N,N-tris(2-hydroxypropyl)amine hydrochloride
4-methoxy-aniline
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With tin(ll) chloride; dihydridotetrakis(triphenylphosphine)ruthenium In 1,4-dioxane; water at 180℃; for 20h; | 37% |
1-(5-methoxy-2-nitrophenyl)propan-2-one
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With sodium dithionite In tetrahydrofuran; water at 20℃; Large scale reaction; | 37% |
5-methoxy-2methyl-1H-indole-3-carboxylic acid
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With glycerol at 140℃; |
(E)-3-Ureido-but-2-enoic acid ethyl ester
acetone(4-methoxyphenyl)hydrazone
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
at 110℃; im Vakuum; |
Conditions | Yield |
---|---|
With zinc(II) chloride at 110℃; | |
With zinc(II) chloride at 140℃; Fisher indole cyclization; |
ethyl 5-methoxy-2-methyl-1H-indole-3-carboxylate
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With sodium hydroxide; ethanol; water |
n-octyl acetate
4-methoxy-2-trimethylsilylmethylbenzanilide
A
5-methoxy-2-methyl-1H-indole
B
n-octyl benzoate
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethylpiperidinyl-lithium 1) -10 degC, THF, 2) 0 degC, 20 min; Yield given. Multistep reaction; |
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With water at 25℃; Rate constant; |
triisopropanolamine
4-methoxy-aniline
A
5-methoxy-2-methyl-1H-indole
B
5-methoxy-3-methyl-1H-indole
Conditions | Yield |
---|---|
With tin(ll) chloride; ruthenium trichloride; triphenylphosphine In 1,4-dioxane at 180℃; for 20h; Yield given. Yields of byproduct given; |
5-methoxy-2-methyl-1H-indole
4-methoxyphenylhydrazine hydrochloride
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / 2-methyl-propan-2-ol / 0.5 h / Heating 2: 96 percent / thiosalicylic acid / trifluoroacetic acid / 1.5 h / Ambient temperature View Scheme |
2‐(bromomethyl)‐4‐methoxy‐1‐nitrobenzene
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: toluene / 1.) 6 h, RT; 2.) 3 h, 100 deg C 2: 74 percent / 48percent HBr, Zn / ethanol / 2 h / Heating 3: 92 percent / pyridine / CH2Cl2 / 1 h / Heating 4: 97 percent / t-BuOK / toluene / 0.25 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: N-bromosuccinimide (NBS), azoisobutyronitrile (AIBN) / CCl4 / 3 h / Heating 2: toluene / 1.) 6 h, RT; 2.) 3 h, 100 deg C 3: 74 percent / 48percent HBr, Zn / ethanol / 2 h / Heating 4: 92 percent / pyridine / CH2Cl2 / 1 h / Heating 5: 97 percent / t-BuOK / toluene / 0.25 h / Heating View Scheme |
bromure d'amino-2 methoxy-5 benzyltriphenylphosphonium
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 92 percent / pyridine / CH2Cl2 / 1 h / Heating 2: 97 percent / t-BuOK / toluene / 0.25 h / Heating View Scheme |
bromure de nitro-2 methoxy-5 benzyltriphenylphosphonium
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 74 percent / 48percent HBr, Zn / ethanol / 2 h / Heating 2: 92 percent / pyridine / CH2Cl2 / 1 h / Heating 3: 97 percent / t-BuOK / toluene / 0.25 h / Heating View Scheme |
dihydroxy-methyl-borane
2-bromo-5-methoxy-1H-indole
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane Suzuki coupling; Reflux; |
ethyl 2-(5-fluoro-2-nitrophenyl)-3-oxobutanoate
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sulfuric acid; acetic acid / 30 - 70 °C / Large scale reaction 2: methanol / 30 - 35 °C / Large scale reaction 3: sodium dithionite / tetrahydrofuran; water / 20 °C / Large scale reaction View Scheme |
1-(5-fluoro-2-nitrophenyl)propan-2-one
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanol / 30 - 35 °C / Large scale reaction 2: sodium dithionite / tetrahydrofuran; water / 20 °C / Large scale reaction View Scheme |
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
Stage #1: 5-methoxy-2-methyl-1H-indole With potassium hydroxide In N,N-dimethyl-formamide for 0.333333h; Stage #2: With iodine In N,N-dimethyl-formamide for 1h; | 100% |
5-methoxy-2-methyl-1H-indole
2,3,5,6-tetramethyl-4-oxo-1-phenylthiocyclohexa-2,5-dienyl 2-chloroacetate
A
5-methoxy-2-methyl-3-(phenylthio)-1H-indole
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 0.166667h; Yields of byproduct given; | A 99% B n/a |
5-methoxy-2-methyl-1H-indole
2,3,5,6-tetramethyl-4-oxo-1-phenylthiocyclohexa-2,5-dienyl 2-chloroacetate
5-methoxy-2-methyl-3-(phenylthio)-1H-indole
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 20℃; for 0.166667h; | 99% |
5-methoxy-2-methyl-1H-indole
1-(2,3,4,5,6-pentafluorophenylthio)-2,3,5,6-tetramethyl-4-oxocyclohexa-2,5-dienyl 2-chloroacetate
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -30 - 0℃; for 0.166667h; | A n/a B 99% |
5-methoxy-2-methyl-1H-indole
3-bromo-5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With N-Bromosuccinimide; silica gel In dichloromethane for 0.5h; | 99% |
With N-Bromosuccinimide; silica gel In dichloromethane at 20℃; for 0.5h; | 99% |
With N-Bromosuccinimide; silica gel In dichloromethane at 20℃; for 0.5h; Inert atmosphere; | 93% |
With bromine In N,N-dimethyl-formamide at 20℃; for 0.5h; | |
With N-Bromosuccinimide In dichloromethane at 20℃; for 1h; Inert atmosphere; |
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With diphenyl hydrogen phosphate In 1,2-dichloro-ethane at 20℃; | 99% |
5-methoxy-2-methyl-1H-indole
hexyl-methyl-ketone
5-methoxy-2-methyl-3-(1-methylheptyl)-1H-indole
Conditions | Yield |
---|---|
With indium(III) tris[bis(trifluoromethanesulfonyl)amide]; methyldiphenylsilane In 1,4-dioxane at 50℃; for 24h; Inert atmosphere; Schlenk technique; | 99% |
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol; RuBF4((S,S)-N-Me-Msdpen)(p-cymene); hydrogen at 10℃; under 37503.8 Torr; for 7h; Autoclave; enantioselective reaction; | 99% |
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With hydrogenchloride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S,R)-ZhaoPhos; hydrogen; acetic acid In dichloromethane at 25℃; under 30402 Torr; for 48h; Autoclave; enantioselective reaction; | 99% |
5-methoxy-2-methyl-1H-indole
methyl iodide
5-methoxy-1,2-dimethyl-1H-indole
Conditions | Yield |
---|---|
With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.833333h; | 98% |
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 1h; | 80% |
Stage #1: 5-methoxy-2-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 80% |
5-methoxy-2-methyl-1H-indole
2-methyl-1H-indol-5-ol
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane at 0 - 20℃; for 2h; | 98% |
With boron tribromide In dichloromethane; water | 93% |
Stage #1: 5-methoxy-2-methyl-1H-indole With boron tribromide In dichloromethane at -78 - 20℃; for 0.5h; Inert atmosphere; Stage #2: With water; sodium hydrogencarbonate In dichloromethane Cooling with ice; | 93% |
5-methoxy-2-methyl-1H-indole
di-tert-butyl dicarbonate
Conditions | Yield |
---|---|
With dmap In acetonitrile at 20℃; for 22h; | 98% |
With dmap In acetonitrile at 20℃; | 0.92 g |
5-methoxy-2-methyl-1H-indole
tert-butyl ((ethylthio)(phenyl)methyl)carbamate
tert-butyl (5-methoxy-2-methyl-1H-indol-3-yl)(phenyl)methylcarbamate
Conditions | Yield |
---|---|
With N-iodo-succinimide In dichloromethane at -78℃; for 0.0833333h; Friedel-Crafts Alkylation; Sealed tube; Inert atmosphere; chemoselective reaction; | 98% |
3',5'-dimethoxy-[1,1'-biphenyl]-2-carbaldehyde
5-methoxy-2-methyl-1H-indole
3-(1,3-dimethoxy-9H-fluoren-9-yl)-5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
Stage #1: 5-methoxy-2-methyl-1H-indole With (S)-3,3’-bis(9-anthracenyl)-1,1’-binaphthyl-2,2’-diyl N-triflyl-phosphoramide In o-xylene at -15 - 20℃; for 0.166667h; Friedel Crafts alkylation; Molecular sieve; Inert atmosphere; Stage #2: 3',5'-dimethoxy-[1,1'-biphenyl]-2-carbaldehyde In o-xylene at -15℃; Friedel Crafts acylation; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 97% |
5-methoxy-2-methyl-1H-indole
ethyl-3,3,3-trifluoropyruvate
Ethyl 3,3,3-trifluoro-2-hydroxy-2-(5-methoxy-2-methyl-indol-3-yl)propionate
Conditions | Yield |
---|---|
With (SIr,RC)-[(η5-C5Me5)Ir{(R)-propane-1,2-diylbis(diphenylphosphane)}(H2O)][SbF6]2 In dichloromethane for 0.233333h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; Optical yield = 55 %ee; | 97% |
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With diphenyl hydrogen phosphite In 1,2-dichloro-ethane at 20℃; | 97% |
5-methoxy-2-methyl-1H-indole
(2-nitroethenyl)benzene
5-methoxy-2-methyl-3-(2-nitro-1-phenylethyl)-1H-indole
Conditions | Yield |
---|---|
In water at 150℃; for 0.1h; Michael addition; Microwave irradiation; | 96% |
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-pyridine In dichloromethane at 25℃; for 0.666667h; regioselective reaction; | 96% |
5-methoxy-2-methyl-1H-indole
cyclopent-2-enone
3-(2-methyl-5-methoxy-1H-indol-3-yl)cyclopentanone
Conditions | Yield |
---|---|
With aminosulfonic acid In acetonitrile at 80℃; for 8h; Michael condensation; | 95% |
With gluconic acid In water at 100℃; for 10h; Michael addition; | 90% |
5-methoxy-2-methyl-1H-indole
5-bromo-2-(2,5-dihydro-1H-pyrrol-1-yl)benzaldehyde
Conditions | Yield |
---|---|
With diphenyl hydrogen phosphite In 1,2-dichloro-ethane at 20℃; | 95% |
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer In acetonitrile at 80℃; for 12h; | 95% |
With chloro(1,5-cyclooctadiene)rhodium(I) dimer In acetonitrile at 80℃; under 760.051 Torr; for 12h; Schlenk technique; | 95% |
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With diphenyl hydrogen phosphite In 1,2-dichloro-ethane at 20℃; | 94% |
5-methoxy-2-methyl-1H-indole
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate In dichloromethane at 20℃; for 5h; regioselective reaction; | 94% |
5-methoxy-2-methyl-1H-indole
1-(1-azidovinyl)-4-fluorobenzene
Conditions | Yield |
---|---|
With indium(III) chloride In dichloromethane at 28 - 30℃; for 6h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With bis[(trifluoromethanesulfonyl)imidate]-2-(dicyclohexyl(2’,6’-dimethoxybiphenyl))phosphine gold(I) In acetonitrile at 30℃; for 24h; | 94% |
IUPAC Name: 5-methoxy-2-methyl-1H-indole
Synonyms of 1H-Indole,5-methoxy-2-methyl- (CAS NO.1076-74-0): EINECS 214-066-5 ; 5-Methoxy-2-methylindole
CAS NO: 1076-74-0
Molecular Formula: C10H11NO
Molecular Weight of 1H-Indole,5-methoxy-2-methyl- (CAS NO.1076-74-0): 161.2004
Molecular Structure:
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 14.16 Å2
Index of Refraction: 1.621
Molar Refractivity: 50.03 cm3
Molar Volume: 142.1 cm3
Surface Tension: 43.4 dyne/cm
Density of 1H-Indole,5-methoxy-2-methyl- (CAS NO.1076-74-0): 1.134 g/cm3
Flash Point: 113.1 °C
Enthalpy of Vaporization: 52.73 kJ/mol
Boiling Point: 308.5 °C at 760 mmHg
Vapour Pressure: 0.00123 mmHg at 25°C
Melting point: 86-88 °C
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 37/39-26
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.
WGK Germany: 3
HazardClass: IRRITANT
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