Product Name

  • Name

    5-METHOXY-2-METHYLINDOLE

  • EINECS 214-066-5
  • CAS No. 1076-74-0
  • Article Data42
  • CAS DataBase
  • Density 1.134 g/cm3
  • Solubility
  • Melting Point 86-88 °C(lit.)
  • Formula C10H11NO
  • Boiling Point 308.501 °C at 760 mmHg
  • Molecular Weight 161.203
  • Flash Point 113.125 °C
  • Transport Information
  • Appearance white to light beige crystalline powder
  • Safety 37/39-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 1076-74-0 (5-METHOXY-2-METHYLINDOLE)
  • Hazard Symbols IrritantXi
  • Synonyms Indole,5-methoxy-2-methyl- (6CI,7CI,8CI);2-Methyl-5-methoxyindole;5-Methoxy-2-methyl-1H-indole;5-Methoxy-2-methylindole;5-Methoxy-2-methyllindole;NSC 63817;
  • PSA 25.02000
  • LogP 2.48490

Synthetic route

methyl 5-methoxy-2-methyl-1H-indole-1-carboxylate

methyl 5-methoxy-2-methyl-1H-indole-1-carboxylate

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
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
104894-18-0

bromure d'acetylamino-2 methoxy-5 benzyltriphenylphosphonium

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With potassium tert-butylate In toluene for 0.25h; Heating;97%
5-methoxy-2-methyl-3-(phenylthio)-1H-indole
98055-12-0

5-methoxy-2-methyl-3-(phenylthio)-1H-indole

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With thiosalicilyc acid In trifluoroacetic acid for 1.5h; Ambient temperature;96%
4-methoxy-2-(prop-1-yn-1-yl)aniline
938052-33-6

4-methoxy-2-(prop-1-yn-1-yl)aniline

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With Pd(II)-Y zeolites In toluene at 110℃; for 20h; Catalytic behavior;96%
With palladium dichloride In acetonitrile at 85℃; Inert atmosphere;
4-methoxy-aniline
104-94-9

4-methoxy-aniline

hydroxy-2-propanone
116-09-6

hydroxy-2-propanone

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With acetic acid for 8h; Reagent/catalyst; Reflux; Large scale;94%
5-methoxy-2-methyl-1-tosyl-1H-indole

5-methoxy-2-methyl-1-tosyl-1H-indole

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; ethanol for 6h; Reflux;92%
With ethanol; potassium hydroxide In tetrahydrofuran Reflux;
(3-Chloro-4-methoxy-phenyl)-isopropylidene-amine
153865-35-1

(3-Chloro-4-methoxy-phenyl)-isopropylidene-amine

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With sodium amide; sodium t-butanolate In tetrahydrofuran at 20℃; for 24h;87%
4-methoxy-aniline
104-94-9

4-methoxy-aniline

acetone
67-64-1

acetone

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
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
181651-13-8

N-(4-methoxyphenyl)-1-methylethenesulfinamide

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at -30℃; for 4h;75%
2-methyl-3-methylthio-5-methoxy-1H-indole
50461-37-5

2-methyl-3-methylthio-5-methoxy-1H-indole

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
aluminum nickel72%
5-methoxy-2-nitro-benzaldehyde
20357-24-8

5-methoxy-2-nitro-benzaldehyde

tert-butyl 2-(triphenylphosphoranylidene)propionate
56904-86-0

tert-butyl 2-(triphenylphosphoranylidene)propionate

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With triphenylphosphine In diphenylether at 260℃; for 1h;48%
N,N,N-tris(2-hydroxypropyl)amine hydrochloride
58901-12-5

N,N,N-tris(2-hydroxypropyl)amine hydrochloride

4-methoxy-aniline
104-94-9

4-methoxy-aniline

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
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
25981-89-9

1-(5-methoxy-2-nitrophenyl)propan-2-one

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With sodium dithionite In tetrahydrofuran; water at 20℃; Large scale reaction;37%
5-methoxy-2methyl-1H-indole-3-carboxylic acid
32387-22-7

5-methoxy-2methyl-1H-indole-3-carboxylic acid

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With glycerol at 140℃;
(E)-3-Ureido-but-2-enoic acid ethyl ester
5435-44-9, 22243-66-9

(E)-3-Ureido-but-2-enoic acid ethyl ester

acetone(4-methoxyphenyl)hydrazone
1078-72-4

acetone(4-methoxyphenyl)hydrazone

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
at 110℃; im Vakuum;
acetone(4-methoxyphenyl)hydrazone
1078-72-4

acetone(4-methoxyphenyl)hydrazone

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With zinc(II) chloride at 110℃;
With zinc(II) chloride at 140℃; Fisher indole cyclization;
ethyl 5-methoxy-2-methyl-1H-indole-3-carboxylate
34572-31-1

ethyl 5-methoxy-2-methyl-1H-indole-3-carboxylate

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With sodium hydroxide; ethanol; water
n-octyl acetate
112-14-1

n-octyl acetate

4-methoxy-2-trimethylsilylmethylbenzanilide
117616-04-3

4-methoxy-2-trimethylsilylmethylbenzanilide

A

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

B

n-octyl benzoate
94-50-8

n-octyl benzoate

Conditions
ConditionsYield
With 2,2,6,6-tetramethylpiperidinyl-lithium 1) -10 degC, THF, 2) 0 degC, 20 min; Yield given. Multistep reaction;
C10H10(3)HNO

C10H10(3)HNO

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With water at 25℃; Rate constant;
triisopropanolamine
122-20-3

triisopropanolamine

4-methoxy-aniline
104-94-9

4-methoxy-aniline

A

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

B

5-methoxy-3-methyl-1H-indole
21987-25-7

5-methoxy-3-methyl-1H-indole

Conditions
ConditionsYield
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-indole-carboxylic acid-(3)

5-methoxy-2-methyl-indole-carboxylic acid-(3)

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

4-methoxyphenylhydrazine hydrochloride
19501-58-7

4-methoxyphenylhydrazine hydrochloride

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
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
67567-46-8

2‐(bromomethyl)‐4‐methoxy‐1‐nitrobenzene

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
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
5-methoxy-2-nitrotoluene
5367-32-8

5-methoxy-2-nitrotoluene

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
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
104894-16-8

bromure d'amino-2 methoxy-5 benzyltriphenylphosphonium

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
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
104894-14-6

bromure de nitro-2 methoxy-5 benzyltriphenylphosphonium

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
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
13061-96-6

dihydroxy-methyl-borane

2-bromo-5-methoxy-1H-indole
169383-96-4

2-bromo-5-methoxy-1H-indole

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane Suzuki coupling; Reflux;
ethyl 2-(5-fluoro-2-nitrophenyl)-3-oxobutanoate
1266659-05-5

ethyl 2-(5-fluoro-2-nitrophenyl)-3-oxobutanoate

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
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
1266659-06-6

1-(5-fluoro-2-nitrophenyl)propan-2-one

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
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
1076-74-0

5-methoxy-2-methyl-1H-indole

2-methyl-5-methoxy-3-iodo-1H-indole

2-methyl-5-methoxy-3-iodo-1H-indole

Conditions
ConditionsYield
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
1076-74-0

5-methoxy-2-methyl-1H-indole

2,3,5,6-tetramethyl-4-oxo-1-phenylthiocyclohexa-2,5-dienyl 2-chloroacetate
194720-38-2

2,3,5,6-tetramethyl-4-oxo-1-phenylthiocyclohexa-2,5-dienyl 2-chloroacetate

A

5-methoxy-2-methyl-3-(phenylthio)-1H-indole
98055-12-0

5-methoxy-2-methyl-3-(phenylthio)-1H-indole

B

4-hydroxy-2,3,5,6-tetramethylphenyl 2-chloroacetate

4-hydroxy-2,3,5,6-tetramethylphenyl 2-chloroacetate

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 0.166667h; Yields of byproduct given;A 99%
B n/a
5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

2,3,5,6-tetramethyl-4-oxo-1-phenylthiocyclohexa-2,5-dienyl 2-chloroacetate
194720-38-2

2,3,5,6-tetramethyl-4-oxo-1-phenylthiocyclohexa-2,5-dienyl 2-chloroacetate

5-methoxy-2-methyl-3-(phenylthio)-1H-indole
98055-12-0

5-methoxy-2-methyl-3-(phenylthio)-1H-indole

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 20℃; for 0.166667h;99%
5-methoxy-2-methyl-1H-indole
1076-74-0

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
335642-28-9

1-(2,3,4,5,6-pentafluorophenylthio)-2,3,5,6-tetramethyl-4-oxocyclohexa-2,5-dienyl 2-chloroacetate

A

4-hydroxy-2,3,5,6-tetramethylphenyl 2-chloroacetate

4-hydroxy-2,3,5,6-tetramethylphenyl 2-chloroacetate

B

3-(2,3,4,5,6-pentafluorophenylthio)-5-methoxy-2-methylindole

3-(2,3,4,5,6-pentafluorophenylthio)-5-methoxy-2-methylindole

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -30 - 0℃; for 0.166667h;A n/a
B 99%
5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

3-bromo-5-methoxy-2-methyl-1H-indole
883141-55-7

3-bromo-5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
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
1076-74-0

5-methoxy-2-methyl-1H-indole

2-(2,5-dihydro-1H-pyrrol-1-yl)benzaldehyde

2-(2,5-dihydro-1H-pyrrol-1-yl)benzaldehyde

3-(2-(1H-pyrrol-1-yl)benzyl)-5-methoxy-2-methyl-1H-indole

3-(2-(1H-pyrrol-1-yl)benzyl)-5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With diphenyl hydrogen phosphate In 1,2-dichloro-ethane at 20℃;99%
5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

hexyl-methyl-ketone
111-13-7

hexyl-methyl-ketone

5-methoxy-2-methyl-3-(1-methylheptyl)-1H-indole
1251532-65-6

5-methoxy-2-methyl-3-(1-methylheptyl)-1H-indole

Conditions
ConditionsYield
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
1076-74-0

5-methoxy-2-methyl-1H-indole

(-)-5-methoxy-2-methylindoline

(-)-5-methoxy-2-methylindoline

Conditions
ConditionsYield
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
1076-74-0

5-methoxy-2-methyl-1H-indole

(S)-2-methyl-5-methoxyindoline

(S)-2-methyl-5-methoxyindoline

Conditions
ConditionsYield
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
1076-74-0

5-methoxy-2-methyl-1H-indole

methyl iodide
74-88-4

methyl iodide

5-methoxy-1,2-dimethyl-1H-indole
17591-06-9

5-methoxy-1,2-dimethyl-1H-indole

Conditions
ConditionsYield
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
1076-74-0

5-methoxy-2-methyl-1H-indole

2-methyl-1H-indol-5-ol
13314-85-7

2-methyl-1H-indol-5-ol

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 0 - 20℃; for 2h;98%
With boron tribromide In dichloromethane; water93%
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
1076-74-0

5-methoxy-2-methyl-1H-indole

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl 5-methoxy-2-methyl-1H-indole-1-carboxylate

tert-butyl 5-methoxy-2-methyl-1H-indole-1-carboxylate

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 22h;98%
With dmap In acetonitrile at 20℃;0.92 g
5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

tert-butyl ((ethylthio)(phenyl)methyl)carbamate
1323902-49-3

tert-butyl ((ethylthio)(phenyl)methyl)carbamate

tert-butyl (5-methoxy-2-methyl-1H-indol-3-yl)(phenyl)methylcarbamate
1612786-56-7

tert-butyl (5-methoxy-2-methyl-1H-indol-3-yl)(phenyl)methylcarbamate

Conditions
ConditionsYield
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
445262-62-4

3',5'-dimethoxy-[1,1'-biphenyl]-2-carbaldehyde

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

3-(1,3-dimethoxy-9H-fluoren-9-yl)-5-methoxy-2-methyl-1H-indole
1372797-84-6

3-(1,3-dimethoxy-9H-fluoren-9-yl)-5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
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
1076-74-0

5-methoxy-2-methyl-1H-indole

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

Ethyl 3,3,3-trifluoro-2-hydroxy-2-(5-methoxy-2-methyl-indol-3-yl)propionate
1297914-66-9

Ethyl 3,3,3-trifluoro-2-hydroxy-2-(5-methoxy-2-methyl-indol-3-yl)propionate

Conditions
ConditionsYield
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
1076-74-0

5-methoxy-2-methyl-1H-indole

2-(2,5-dihydro-1H-pyrrol-1-yl)-4-methylbenzaldehyde

2-(2,5-dihydro-1H-pyrrol-1-yl)-4-methylbenzaldehyde

5-methoxy-2-methyl-3-(4-methyl-2-(1H-pyrrol-1-yl)benzyl)-1H-indole

5-methoxy-2-methyl-3-(4-methyl-2-(1H-pyrrol-1-yl)benzyl)-1H-indole

Conditions
ConditionsYield
With diphenyl hydrogen phosphite In 1,2-dichloro-ethane at 20℃;97%
5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

5-methoxy-2-methyl-3-(2-nitro-1-phenylethyl)-1H-indole
1227380-56-4

5-methoxy-2-methyl-3-(2-nitro-1-phenylethyl)-1H-indole

Conditions
ConditionsYield
In water at 150℃; for 0.1h; Michael addition; Microwave irradiation;96%
5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

2,2,2-trifluoroethyl(2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate

2,2,2-trifluoroethyl(2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate

5-methoxy-2-methyl-3-(2,2,2-trifluoroethyl)-1H-indole

5-methoxy-2-methyl-3-(2,2,2-trifluoroethyl)-1H-indole

Conditions
ConditionsYield
With 2,6-di-tert-butyl-pyridine In dichloromethane at 25℃; for 0.666667h; regioselective reaction;96%
5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

cyclopent-2-enone
930-30-3

cyclopent-2-enone

3-(2-methyl-5-methoxy-1H-indol-3-yl)cyclopentanone
1321804-40-3

3-(2-methyl-5-methoxy-1H-indol-3-yl)cyclopentanone

Conditions
ConditionsYield
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
1076-74-0

5-methoxy-2-methyl-1H-indole

5-bromo-2-(2,5-dihydro-1H-pyrrol-1-yl)benzaldehyde
742100-39-6

5-bromo-2-(2,5-dihydro-1H-pyrrol-1-yl)benzaldehyde

3-(5-bromo-2-(1H-pyrrol-1-yl)benzyl)-5-methoxy-2-methyl-1H-indole

3-(5-bromo-2-(1H-pyrrol-1-yl)benzyl)-5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With diphenyl hydrogen phosphite In 1,2-dichloro-ethane at 20℃;95%
5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

carbon monoxide
201230-82-2

carbon monoxide

2-methyl-5-methoxy-N-p-toluenesulfonyl-1H-indole-3-carboxamide

2-methyl-5-methoxy-N-p-toluenesulfonyl-1H-indole-3-carboxamide

Conditions
ConditionsYield
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
1076-74-0

5-methoxy-2-methyl-1H-indole

2-(2,5-dihydro-1H-pyrrol-1-yl)-4-methoxybenzaldehyde

2-(2,5-dihydro-1H-pyrrol-1-yl)-4-methoxybenzaldehyde

5-methoxy-3-(4-methoxy-2-(1H-pyrrol-1-yl)benzyl)-2-methyl-1H-indole

5-methoxy-3-(4-methoxy-2-(1H-pyrrol-1-yl)benzyl)-2-methyl-1H-indole

Conditions
ConditionsYield
With diphenyl hydrogen phosphite In 1,2-dichloro-ethane at 20℃;94%
ammonium thiocyanate

ammonium thiocyanate

5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

5-methoxy-2-methyl-3-thiocyanato-1H-indole

5-methoxy-2-methyl-3-thiocyanato-1H-indole

Conditions
ConditionsYield
With dipotassium peroxodisulfate In dichloromethane at 20℃; for 5h; regioselective reaction;94%
5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

1-(1-azidovinyl)-4-fluorobenzene
1374152-38-1

1-(1-azidovinyl)-4-fluorobenzene

3-(1-(4-fluorophenyl)vinyl)-5-methoxy-2-methyl-1H-indole

3-(1-(4-fluorophenyl)vinyl)-5-methoxy-2-methyl-1H-indole

Conditions
ConditionsYield
With indium(III) chloride In dichloromethane at 28 - 30℃; for 6h; Inert atmosphere;94%
5-methoxy-2-methyl-1H-indole
1076-74-0

5-methoxy-2-methyl-1H-indole

4-methoxyphenylacetylen
768-60-5

4-methoxyphenylacetylen

5-methoxy-3-(1-(4-methoxyphenyl)vinyl)-2-methyl-1H-indole

5-methoxy-3-(1-(4-methoxyphenyl)vinyl)-2-methyl-1H-indole

Conditions
ConditionsYield
With bis[(trifluoromethanesulfonyl)imidate]-2-(dicyclohexyl(2’,6’-dimethoxybiphenyl))phosphine gold(I) In acetonitrile at 30℃; for 24h;94%

5-Methoxy-2-methyl-1H-indole Chemical Properties

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

5-Methoxy-2-methyl-1H-indole Safety Profile

Hazard Codes: IrritantXi
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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