6-Methoxyindole supplier | CasNO.3189-13-7

Name
6-Methoxyindole
EINECS 221-689-6
CAS No. 3189-13-7
Article Data57
CAS DataBase
Density 1.169 g/cm³
Solubility
Melting Point 90-92 °C(lit.)
Formula C₉H₉NO
Boiling Point 297.8 °C at 760 mmHg
Molecular Weight 147.177
Flash Point 109.2 °C
Transport Information
Appearance white shiny crystals
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 6-Methoxy-1H-indole;1H-Indole, 6-methoxy-;Indole, 6-methoxy-;6-Methoxy-indole;
PSA 25.02000
LogP 2.17650

Synthetic route

: 16732-73-3
6-Methoxyindole-2-carboxylic acid

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
In quinoline for 0.2h; microwave;	99%
With copper In quinoline for 2h; Heating;	97.6%
With quinoline; copper Heating;	87%
With quinoline; copper at 220℃; for 0.2h; Microwave irradiation;	70%
With quinoline; copper oxide-chromium oxide at 200 - 210℃;

: 138344-18-0
tert-butyl 6-methoxy-1H-indole-1-carboxylate

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Heating;	98%

: 107734-26-9
6-methoxy-N-(toluenesulfonyl)indole

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With magnesium In methanol at 20℃; for 1.5h; Sonication;	96%

: 1335101-95-5
1-(E)-(2-(4-methoxy-2-nitrophenyl)vinyl)pyrrolidine

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate In ethanol at 75℃; for 7h;	93%

: 111795-95-0
(5-bromo-4-methoxy-2-nitrophenyl)acetonitrile

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With hydrogen; acetic acid; 10% palladium on active carbon In ethanol under 2280 Torr; for 2h; Ambient temperature;	90%

: 6-methoxy-1-tosylindoline

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
Stage #1: 6-methoxy-1-tosylindoline In tetrahydrofuran at -78℃; for 2h; Stage #2: With oxygen In tetrahydrofuran at 20℃;	86%

: 34158-98-0
acetaldehyde 3-methoxyphenylhydrazone

A: 3189-13-7
6-methoxylindole

B: 4837-90-5
4-methoxy-1H-indole

Conditions

Conditions	Yield
GIPKh-115 In benzene at 260 - 280℃; (g) phase;	A n/a B 85%
GIPKh-115 In benzene at 180 - 320℃; (g) phase. Object of study: effect of electronic factors;	A n/a B 85%
GIPKh-115 at 260 - 280℃; Yield given. Yields of byproduct given;

: 7556-47-0
6-methoxy-2,3-dihydro-1H-indole

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
Stage #1: 6-methoxy-2,3-dihydro-1H-indole In tetrahydrofuran at -78℃; for 2h; Stage #2: With oxygen In tetrahydrofuran at 20℃;	85%
With potassium tert-butylate In o-xylene at 140℃; for 36h; Inert atmosphere;	70%
With oxygen In N,N-dimethyl acetamide at 20℃; Schlenk technique; Irradiation;	44%
With monoamine oxidase D11 In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 168h; pH=7.8; Enzymatic reaction;	40%
Multi-step reaction with 2 steps 1.1: pyridine / dichloromethane 2.1: / tetrahydrofuran / 2 h / -78 °C 2.2: 20 °C View Scheme

: 2,2-dimethoxy-1-(4-methoxy-2-nitrophenyl)ethane

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With hydrogenchloride; iron; acetic acid In ethanol Temp. 70 - 75 deg C, 1 h. Temp. 85 deg C, 2 h;	84%

: 52415-29-9
6-bromo-1H-indole

: 124-41-4
sodium methylate

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With copper(l) iodide In N,N-dimethyl-formamide for 12h;	73%

: cyano-(4-methoxy-2-nitro-phenyl)-acetic acid benzyl ester

A: 3189-13-7
6-methoxylindole

B: 7556-47-0
6-methoxy-2,3-dihydro-1H-indole

C: 605668-99-3
2-(2-amino-ethyl)-5-methoxy-phenylamine

Conditions

Conditions	Yield
With hydrogen; acetic acid; palladium on activated charcoal In ethanol; water at 25℃; under 2585.74 Torr; for 18h;	A 73% B n/a C n/a

...Expand

: 85355-57-3
1-(2-Bromo-2-chloro-ethyl)-4-methoxy-2-nitro-benzene

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With sodium acetate; iron; acetic acid In ethanol; water for 2h; Heating;	71%

: 2380-86-1
6-hydroxy-1H-indole

: 74-88-4
methyl iodide

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at -20℃; for 0.166667h;	68%

: C10H9N3O3

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With quinoline; copper at 220℃; for 0.2h; Microwave irradiation;	56%
Multi-step reaction with 2 steps 1: tetrakis(trifluoroacetato)rhodium(II) / toluene / 0.25 h / 100 °C / Microwave irradiation 2: quinoline; copper / 0.2 h / 220 °C / Microwave irradiation View Scheme

: 74-85-1
ethene

: 5344-78-5
4-bromo-3-nitroanizole

A: 3189-13-7
6-methoxylindole

B: 126759-34-0
1-methoxy-3-nitro-4-vinylbenzene

Conditions

Conditions	Yield
With triethylamine; tris-(o-tolyl)phosphine; palladium diacetate In acetonitrile at 120℃; under 22800 Torr; for 24h;	A 48% B 32%

...Expand

: 88-12-0
1-ethenyl-2-pyrrolidinone

: 59557-92-5
2-bromo-5-methoxyaniline

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine In acetonitrile at 100℃; for 20h; sealed tube;	46%

: 90610-20-1
4-methoxy-1-ethyl-2-nitrobenzene

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With tetrakis(trifluoroacetato)rhodium(II); caesium carbonate In N,N-dimethyl-formamide at 140℃; for 24h; Schlenk technique; Inert atmosphere;	45%

: 126759-34-0
1-methoxy-3-nitro-4-vinylbenzene

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With carbon monoxide; triphenylphosphine; palladium diacetate In acetonitrile under 3040 Torr; for 21h; Heating;	40%
Multi-step reaction with 2 steps 1: 65 percent / O2 (1 atm) / Na2PdCl4 / 24 h 2: 84 percent / Fe, acetic acid, 10percent HCl / ethanol / Temp. 70 - 75 deg C, 1 h. Temp. 85 deg C, 2 h View Scheme
Multi-step reaction with 2 steps 1: 80 percent / oxygen / palladium(II) chloride, copper(I) chloride / 1,2-dimethoxy-ethane / 24 h / 50 - 60 °C 2: 1.) H2, 2.) aq. HCl / 10percent rhodium-carbon / 1.) ethanol, room temperature, 1 atmosphere, 3 h, 2.) room temperature, 3 h View Scheme

: 105896-37-5
N-(3-methoxyphenyl)ethenesulfinamide

A: 3189-13-7
6-methoxylindole

B: 4837-90-5
4-methoxy-1H-indole

Conditions

Conditions	Yield
In toluene at 110℃; for 1h;	A 25% B 5%

: 99459-34-4
2,β-Dinitro-4-methoxy-styrol

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With palladium on activated charcoal; ethanol; ethyl acetate Hydrogenation.Reagens 4: Essigsaeure;
With ethanol; iron; acetic acid

: 123-75-1
pyrrolidine

: 17484-36-5
4-Methyl-3-nitroanisole

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With ammonium acetate; titanium(III) chloride 1) DMF, 100-110 deg C, 3 h, 2) water, DMF, 15 min; Yield given. Multistep reaction;

...Expand

: 17484-36-5
4-Methyl-3-nitroanisole

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With pyrrolidine; dimethylamide dimethyl acetal; hydrogen; palladium on activated charcoal 1.) DMF, 105 deg C, 19 h, 2.) ethyl acetate, 50 p.s.i., 3 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: 4 h / 110 °C 2: TiCl3, 4M NH4OAc / acetone View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 20 h / 115 °C / Inert atmosphere 2: iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate / ethanol / 7 h / 75 °C View Scheme

: 69111-92-8
2-(4-methoxy-2-nitrophenyl)acetaldehyde

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With sodium acetate; iron; acetic acid In ethanol; water for 2h; Heating; Yield given;

: 1-[(E)-2-(4-Methoxy-2-nitro-phenyl)-vinyl]-piperidine

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With titanium(III) chloride; ammonium acetate In acetone Yield given;

: 85355-35-7
Acetic acid 1-chloro-2-(4-methoxy-2-nitro-phenyl)-ethyl ester

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With sodium acetate; iron; acetic acid In ethanol; water for 2h; Heating;

: 75934-38-2
N-(2,2-Diethoxy-ethyl)-2,2,2-trifluoro-N-(3-methoxy-phenyl)-acetamide

A: 3189-13-7
6-methoxylindole

B: 4837-90-5
4-methoxy-1H-indole

Conditions

Conditions	Yield
With potassium hydroxide; trifluoroacetic anhydride 1) CF3COOH, 56 deg C, 56 h; 2) methanol, room temperature; Yield given. Multistep reaction. Yields of byproduct given;

: 126759-42-0
2-<(4-methoxy-2-nitrophenyl)methyl>-1,3-dioxane

: 3189-13-7
6-methoxylindole

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; rhodium contaminated with carbon 1.) ethanol, room temperature, 1 atmosphere, 3 h, 2.) room temperature, 3 h; Yield given. Multistep reaction;

: 102-71-6
triethanolamine

: 536-90-3
m-Anisidine

A: 3189-13-7
6-methoxylindole

B: 4837-90-5
4-methoxy-1H-indole

Conditions

Conditions	Yield
With tin(ll) chloride; ruthenium trichloride; triphenylphosphine In 1,4-dioxane at 180℃; for 20h; Yield given. Yields of byproduct given;

...Expand

6-methoxy-indole-carboxylic acid-(2): 6-methoxy-indole-carboxylic acid-(2)

: 3189-13-7
6-methoxylindole

: 3189-13-7
6-methoxylindole

: 7556-47-0
6-methoxy-2,3-dihydro-1H-indole

Conditions

Conditions	Yield
With borane-THF In tetrahydrofuran at 0℃; for 0.5h;	100%
Stage #1: 6-methoxylindole With sodium cyanoborohydride; acetic acid In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: With water; sodium hydroxide In N,N-dimethyl-formamide	100%
With sodium cyanoborohydride; acetic acid at 20℃; for 3h;	97%

: 3189-13-7
6-methoxylindole

: 30354-18-8
N,N-dimethyl(methylene)ammonium chloride

: 62467-65-6
1-(6-methoxy-1H-indol-3-yl)-N,N-dimethylmethanamine

Conditions

Conditions	Yield
In dichloromethane	100%

: 3189-13-7
6-methoxylindole

: 824-94-2
p-methoxybenzyl chloride

: 1142120-31-7
6-methoxy-N-(4-methoxybenzyl)indole

Conditions

Conditions	Yield
Stage #1: 6-methoxylindole With sodium hydride In N,N-dimethyl-formamide at 25℃; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 25℃; for 12h;	100%

: 3189-13-7
6-methoxylindole

: 192220-12-5, 199463-78-0
(C-benzyloxymethane-N-benzyl)nitrone

: 952235-30-2
1-[N-benzyl-N-(hydroxy)amino]-2-[N'-(tert-butoxycarbonyl)amino]-1-(6'-methoxyindol-3'-yl)ethane

Conditions

Conditions	Yield
Stage #1: 6-methoxylindole; (C-benzyloxymethane-N-benzyl)nitrone With hydrogenchloride In methanol at 0℃; Stage #2: With sodium hydrogencarbonate In methanol; water	100%

: 3189-13-7
6-methoxylindole

: 98-09-9
benzenesulfonyl chloride

: 56995-13-2
6-methoxy-1-(phenylsulfonyl)-1H-indole

Conditions

Conditions	Yield
Stage #1: 6-methoxylindole With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane at 4℃; Inert atmosphere; Sealed tube; Stage #2: benzenesulfonyl chloride In dichloromethane at 4 - 23℃; for 3h; Inert atmosphere; Sealed tube;	99%
Stage #1: 6-methoxylindole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	93.8%
Stage #1: 6-methoxylindole With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 20℃; for 1h;	92%

: 3189-13-7
6-methoxylindole

: 100-39-0
benzyl bromide

: 90811-54-4
1-benzyl-6-methoxy-1H-indole

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 12h;	99%
With potassium hydroxide In dimethyl sulfoxide at 20℃;	93%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere;	91%

: 541-59-3
maleiimide

: 3189-13-7
6-methoxylindole

: 885320-48-9
3-(6-methoxy-1H-indol-3-yl)pyrrolidine-2,5-dione

Conditions

Conditions	Yield
With acetic acid at 190℃; for 2h; Michael addition; microwave irradiation;	99%
In acetic acid at 170℃; for 2h; Microwave irradiation;

: 3189-13-7
6-methoxylindole

: 107969-78-8, 6395-86-4
methyl 4-phenyl-2-oxo-3-butenoate

: 4-(6-methoxyindol-3-yl)-2-oxo-4-phenylbutyric acid methyl ester

Conditions

Conditions	Yield
With C35H48N4O4; samarium(III) trifluoromethanesulfonate In dichloromethane at -20℃; for 0.5h; asymmetric Friedel-Crafts alkylation; Inert atmosphere; optical yield given as %ee;	99%

: 3189-13-7
6-methoxylindole

: 1373942-86-9
tert-butyl 3-((tert-butoxycarbonyl)imino)-2-oxoindoline-1-carboxylate

: tert-butyl (R)-3-((tert-butoxycarbonyl)amino)-3-(6-methoxy-1H-indol-3-yl)-2-oxoindoline-1-carboxylate

Conditions

Conditions	Yield
Stage #1: tert-butyl 3-((tert-butoxycarbonyl)imino)-2-oxoindoline-1-carboxylate With C33H48N4O4; zinc trifluoromethanesulfonate In toluene at 35℃; for 0.5h; Inert atmosphere; Molecular sieve; Stage #2: 6-methoxylindole In toluene at 50℃; for 48h; Friedel-Crafts Alkylation; Inert atmosphere; Molecular sieve; enantioselective reaction;	99%

: 3189-13-7
6-methoxylindole

: C16H18N2O5

: tert-butyl (R)-3-((ethoxycarbonyl)amino)-3-(6-methoxy-1H-indol-3-yl)-2-oxoindoline-1-carboxylate

Conditions

Conditions	Yield
Stage #1: C16H18N2O5 With C33H48N4O4; zinc trifluoromethanesulfonate In toluene at 35℃; for 0.5h; Inert atmosphere; Molecular sieve; Stage #2: 6-methoxylindole In toluene at 50℃; for 48h; Friedel-Crafts Alkylation; Inert atmosphere; Molecular sieve; enantioselective reaction;	99%

: 3189-13-7
6-methoxylindole

: 3-(1-phenylvinyl)-1H-indole

: (R)-3-(1-(1H-indol-3-yl)-1-phenylethyl)-6-methoxy-1H-indole

Conditions

Conditions	Yield
Stage #1: 3-(1-phenylvinyl)-1H-indole With C76H57F12NO6P2 In 1,2-dichloro-ethane at -20℃; for 0.166667h; Molecular sieve; Stage #2: 6-methoxylindole In 1,2-dichloro-ethane at -20℃; for 24h; Molecular sieve; enantioselective reaction;	99%

: 3189-13-7
6-methoxylindole

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 70555-46-3
6-methoxy-1H-indole-3-carbaldehyde

Conditions

Conditions	Yield
With trichlorophosphate at 20℃; for 2.5h;	98%
With trichlorophosphate at 0 - 40℃; Vilsmeier formylation;	89%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate for 0.333333h; Vilsmeier-Haack Formylation; Cooling with ice; Stage #2: 6-methoxylindole at 20℃; for 1.5h; Vilsmeier-Haack Formylation;	59%

: 3189-13-7
6-methoxylindole

: 18162-48-6
tert-butyldimethylsilyl chloride

: 180635-97-6
1-(tert-butyldimethylsilyl)-6-methoxy-1H-indole

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 10h;	98%
Stage #1: 6-methoxylindole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.75h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 6h; Inert atmosphere;	79%
Stage #1: 6-methoxylindole With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 0.25h; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; hexane at 0℃; for 3h;

: 3189-13-7
6-methoxylindole

: 1220198-08-2
(2-bromo-ethoxy)-tert-butyl-dimethyl-silane

: 408355-39-5
1-[2-(tert-butyldimethylsilyloxy)-eth-1-yl]-6-methoxy-1H-indole

Conditions

Conditions	Yield
In N,N-dimethyl-formamide	98%

: 3189-13-7
6-methoxylindole

: 1533443-74-1
ethyl 5-methyl-2-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-3-carboxylate

: 1533444-34-6
ethyl (R)-3-(6-methoxy-1H-indol-3-yl)-5-methyl-2-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-3-carboxylate

Conditions

Conditions	Yield
With C38H33O4P In toluene at -78℃; for 6h; enantioselective reaction;	98%

: 3189-13-7
6-methoxylindole

: 100-51-6
benzyl alcohol

: 3-benzyl-6-methoxy-1H-indole

Conditions

Conditions	Yield
With C18H18Cl4N2Ni2O2; potassium 2-methylbutan-2-olate In neat (no solvent) at 140℃; for 6h;	98%
Stage #1: 6-methoxylindole; benzyl alcohol With potassium phosphate; C24H20FeN2O4 In neat (no solvent) at 20℃; for 2h; Schlenk technique; Inert atmosphere; UV-irradiation; Stage #2: In neat (no solvent) at 110℃; for 16h; Schlenk technique; Inert atmosphere;	73%

: 3189-13-7
6-methoxylindole

: 302912-31-8
ethyl-4-cyanobenzoylformate

: (4-cyano-phenyl)-hydroxy-(6-methoxy-1H-indol-3-yl)-acetic acid ethyl ester

Conditions

Conditions	Yield
With PHN-DHQ-OH In diethyl ether at 23℃; for 58h; Friedel-Crafts reaction;	97%

: 3189-13-7
6-methoxylindole

: 302912-31-8
ethyl-4-cyanobenzoylformate

: (4-cyano-phenyl)-hydroxy-(6-methoxy-1H-indol-3-yl)-acetic acid ethyl ester

Conditions

Conditions	Yield
With 4-((S)-(phenanthren-9-yloxy)((2R,4S,8R)-8-vinylquinuclidin-2-yl)methyl)quinolin-6-ol In diethyl ether at 23℃; for 59h; Friedel-Crafts reaction;	97%

: 3189-13-7
6-methoxylindole

: 7669-54-7
2-nitrobenzenesulfenyl chloride

: 691399-75-4
6-methoxy-3-(2-nitro-phenylsulfanyl)-1H-indole

Conditions

Conditions	Yield
In diethyl ether at 20℃; for 1.06667h;	97%

: 3189-13-7
6-methoxylindole

: 13154-24-0
triisopropylsilyl chloride

: 6-methoxy-1-(triisopropylsilyl)-1H-indole

Conditions

Conditions	Yield
Stage #1: 6-methoxylindole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Stage #2: triisopropylsilyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃;	97%

: 3189-13-7
6-methoxylindole

: 50-00-0
formaldehyd

: 124-40-3
dimethyl amine

: 62467-65-6
1-(6-methoxy-1H-indol-3-yl)-N,N-dimethylmethanamine

Conditions

Conditions	Yield
In acetic acid for 15h; Ambient temperature;	96%
With ethanol; acetic acid
With 1,4-dioxane; acetic acid
With acetic acid at 0 - 20℃; for 4h;
With acetic acid at 0 - 25℃; for 12h;

...Expand

: 3189-13-7
6-methoxylindole

: 24424-99-5
di-tert-butyl dicarbonate

: 138344-18-0
tert-butyl 6-methoxy-1H-indole-1-carboxylate

Conditions

Conditions	Yield
With dmap In dichloromethane at 20℃; for 8h; Inert atmosphere;	96%
With dmap In dichloromethane at 0 - 20℃; Inert atmosphere;	90%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h;	89%
With dmap In dichloromethane at 40℃;	86%

: 3189-13-7
6-methoxylindole

: 75-36-5
acetyl chloride

: 99532-52-2
1-(6-methoxy-1H-indol-3-yl)ethan-1-one

Conditions

Conditions	Yield
Stage #1: 6-methoxylindole With diethylaluminium chloride In hexane; dichloromethane at 0℃; for 0.5h; Stage #2: acetyl chloride In hexane; dichloromethane at 50℃; for 0.166667h; microwave irradiation; Further stages.;	96%
Stage #1: 6-methoxylindole With diethylaluminium chloride In hexane; dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: acetyl chloride In hexane; dichloromethane at 0℃; Inert atmosphere;
Stage #1: 6-methoxylindole; acetyl chloride In toluene at 0℃; for 0.166667h; Stage #2: With tin(IV) chloride In toluene for 12h;
Stage #1: 6-methoxylindole With diethylaluminium chloride In hexane; dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: acetyl chloride In hexane; dichloromethane at 0℃; Inert atmosphere;

: 636-98-6
p-nitrobenzene iodide

: 3189-13-7
6-methoxylindole

: 1234333-70-0
6-methoxy-1-(4-nitrophenyl)-1H-indole

Conditions

Conditions	Yield
With 1,2-ethanedione dioxime; tetrabutylammomium bromide; copper(l) chloride; sodium hydroxide In water at 100℃; for 24h; Inert atmosphere; sealed tube;	96%

: 3189-13-7
6-methoxylindole

: 372-09-8
cyanoacetic acid

: 1082892-90-7
3-(6-methoxy-1H-indol-3-yl)-3-oxopropanenitrile

Conditions

Conditions	Yield
With propionic acid anhydride at 65 - 75℃; for 0.116667h;	96%
With propionic acid anhydride at 100℃;

: 3189-13-7
6-methoxylindole

: 74-83-9
methyl bromide

: 1968-17-8
6-methoxy-1-methyl-1H-indole

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃;	96%

: 3189-13-7
6-methoxylindole

: 3612-20-2
1-phenylmethyl-4-piperidone

: 52157-77-4
6-methoxy-3-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Conditions

Conditions	Yield
With sodium methylate In methanol for 5h; Heating;	95%

6-Methoxyindole Specification

The IUPAC name of 6-Methoxyindole is 6-methoxy-1H-indole. With the CAS registry number 3189-13-7, it is also named as 1H-Indole, 6-methoxy-. The product's categories are Blocks; Indoles Oxindoles; Indole / Indoline / Oxindole; Indole and Indoline; Pharmacetical; Pyrroles & Indoles; Indoles; Indole Series; Simple Indoles; Indole; Pyrroles & Indoles; Building Blocks; Heterocyclic Building Blocks. Besides, it is white shiny crystals, which should be stored in closed, cool and dry place. It is light sensitive. In addition, its molecular formula is C₉H₉NO and molecular weight is 147.18.

The other characteristics of this product can be summarized as: (1)EINECS: 221-689-6; (2)ACD/LogP: 2.00; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 2; (5)ACD/LogD (pH 7.4): 2; (6)ACD/BCF (pH 5.5): 19.42; (7)ACD/BCF (pH 7.4): 19.42; (8)ACD/KOC (pH 5.5): 290.94; (9)ACD/KOC (pH 7.4): 290.94; (10)#H bond acceptors: 2; (11)#H bond donors: 1; (12)#Freely Rotating Bonds: 1; (13)Index of Refraction: 1.637; (14)Molar Refractivity: 45.2 cm³; (15)Molar Volume: 125.8 cm³; (16)Surface Tension: 45.7 dyne/cm; (17)Density: 1.169 g/cm³; (18)Flash Point: 109.2 °C; (19)Melting point: 90-94 °C; (20)Enthalpy of Vaporization: 51.61 kJ/mol; (21)Boiling Point: 297.8 °C at 760 mmHg; (22)Vapour Pressure: 0.00234 mmHg at 25 °C.

Preparation of 6-Methoxyindole: this chemical can be prepared by 6-Methoxy-indole-2-carboxylic acid.

This reaction needs Quinoline by microwave. The reaction time is 12 min. The yield is 99 %.

Uses of 6-Methoxyindole: it can react with 2-Nitro-propene to get 6-Methoxy-3-(2-nitro-propyl)-indole.

This reaction needs Benzene by heating. The yield is 67 %.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
(1)SMILES: COc1ccc2cc[nH]c2c1
(2)InChI: InChI=1/C9H9NO/c1-11-8-3-2-7-4-5-10-9(7)6-8/h2-6,10H,1H3
(3)InChIKey: QJRWYBIKLXNYLF-UHFFFAOYAN
(4)Std. InChI: InChI=1S/C9H9NO/c1-11-8-3-2-7-4-5-10-9(7)6-8/h2-6,10H,1H3
(5)Std. InChIKey: QJRWYBIKLXNYLF-UHFFFAOYSA-N

Product Name

6-Methoxyindole

Synthetic route

6-Methoxyindole Specification

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