4-Methoxyindole supplier | CasNO.4837-90-5

Name
4-Methoxyindole
EINECS -0
CAS No. 4837-90-5
Article Data45
CAS DataBase
Density 1.169 g/cm³
Solubility
Melting Point 69-70 °C(lit.)
Formula C₉H₉NO
Boiling Point 306.9 °C at 760 mmHg
Molecular Weight 147.177
Flash Point 109.2 °C
Transport Information
Appearance light brown to grey crystalline powder
Safety 26-36-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 4-methoxy-1H-indole;1H-Indole, 4-methoxy-;4-Methoxy Indole;4-Methoxy-indole;
PSA 25.02000
LogP 2.17650

Synthetic route

: 103260-65-7
4-methoxy-1H-indole-2-carboxylic acid

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

Conditions

Conditions	Yield
In quinoline for 0.2h; microwave;	97%
With quinoline; copper for 2h; Heating;	94%
copper In quinoline for 2h; Heating / reflux;	94%
With quinoline; copper oxide-chromium oxide at 200 - 210℃;

: 20876-27-1
(6-methoxy-2-nitrophenyl)acetonitrile

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

Conditions

Conditions	Yield
With hydrogen; acetic acid; 10% palladium on active carbon In ethanol under 2280 Torr; for 2h; Ambient temperature;	96%
With palladium 10% on activated carbon; hydrogen; acetic acid at 20℃; for 12h;

: 112970-67-9
4-methoxy-1-<(4-methylphenyl)sulfonyl>indole

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

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 12h; Heating;	96%
With sodium hydride In N,N-dimethyl acetamide at 60℃; for 3h; Inert atmosphere;	74%

: 2380-94-1
1H-indol-4-ol

: 74-88-4
methyl iodide

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

Conditions

Conditions	Yield
With potassium carbonate In methanol; butanone for 6h; Heating;	95%
Stage #1: 1H-indol-4-ol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; for 1h;	92%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	91%

: 2-ethenyl-3-methoxynitrobenzene

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

Conditions

Conditions	Yield
With carbon monoxide; triphenylphosphine; palladium diacetate In acetonitrile under 3040 Torr; for 20h; Heating;	89%

: 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;

: 2-methoxy-6-nitrophenylacetaldehyde semicarbazone

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

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 3102.9 Torr; for 6h;	82%

: 7555-94-4
2,3-dihydro-4-methoxy-1H-indole

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

Conditions

Conditions	Yield
With C55H49N4OP2Ru In o-xylene at 140℃; under 750.075 Torr; for 48h; Inert atmosphere; Schlenk technique; Green chemistry;	82%
With potassium tert-butylate In o-xylene at 140℃; for 36h; Inert atmosphere;	55%

: 96631-91-3
3-methoxy-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene

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

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In tetrahydrofuran for 1h;	70%
With hydrogen; palladium on activated charcoal In methanol; dichloromethane at 20℃;	63%

: (3-Methoxy-2-trimethylsilanylethynyl-phenyl)-carbamic acid tert-butyl ester

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

Conditions

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol for 5h; Heating;	70%

: [(E)-2-(2-Methoxy-6-nitro-phenyl)-vinyl]-dimethyl-amine

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

Conditions

Conditions	Yield
With titanium(III) chloride; ammonium acetate buffer for 0.166667h;	61%

: 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%

: 22630-08-6
tris(piperidino)-methane

: 4837-88-1
6-methoxy-2-nitrotoluene

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

Conditions

Conditions	Yield
With iron; silica gel 1) 120 deg C, 4 h, under vacuum 2) 1 h reflux in toluene-acetic acid; Yield given. Multistep reaction;

: 85355-48-2
(2-Methoxy-6-nitro-phenyl)-acetaldehyde

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

Conditions

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

: 117609-03-7
1-[(E)-2-(2-Methoxy-6-nitro-phenyl)-vinyl]-piperidine

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

Conditions

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

: 85355-37-9
Acetic acid 1-chloro-2-(2-methoxy-6-nitro-phenyl)-ethyl ester

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

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;

: 4837-88-1
6-methoxy-2-nitrotoluene

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

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

Conditions

Conditions	Yield
With pyrrolidine; hydrazine hydrate; nickel 1.) DMF, 125 deg C, 3 h; 2.) methanol, 50-60 deg C, 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

4-methoxy-indole-carboxylic acid-(2): 4-methoxy-indole-carboxylic acid-(2)

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

Conditions

Conditions	Yield
at 245 - 250℃;

: 111258-23-2
methyl 4-methoxy-1H-indole-2-carboxylate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / aq. NaOH / 0.5 h / Heating 2: 94 percent / Cu; quinoline / 2 h / Heating View Scheme

: 143702-35-6
(Z)-2-azido-3-(2-methoxyphenyl)acrylic acid methyl ester

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / xylene / 1 h / Heating 2: 99 percent / aq. NaOH / 0.5 h / Heating 3: 94 percent / Cu; quinoline / 2 h / Heating View Scheme

: 135-02-4
ortho-anisaldehyde

(S)-(Fmoc-amino)-cyclohexyl-acetic acid on Wang resin: (S)-(Fmoc-amino)-cyclohexyl-acetic acid on Wang resin

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 68 percent / methanol / 1.5 h / -10 °C 2: 88 percent / xylene / 1 h / Heating 3: 99 percent / aq. NaOH / 0.5 h / Heating 4: 94 percent / Cu; quinoline / 2 h / Heating View Scheme

: 5460-31-1
3-nitro-o-cresol

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 54 percent / CuI; DMF / acetonitrile / 10 h / 180 °C / 6000.6 - 7500.75 Torr / microwave irradiation 2: 63 percent / H2 / Pd/C / methanol; CH2Cl2 / 20 °C View Scheme

: 4837-88-1
6-methoxy-2-nitrotoluene

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / CuI; DMF / 3 h / 180 °C / 6000.6 - 7500.75 Torr / microwave irradiation 2: 63 percent / H2 / Pd/C / methanol; CH2Cl2 / 20 °C View Scheme
Multi-step reaction with 2 steps 1: pyrrolidine / dimethylformamide / 3 h / 125 °C 2: 61 percent / aq. TiCl3, ammonium acetate buffer / 0.17 h View Scheme
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 / 3 h / Reflux 2: zinc; acetic acid; hydrogenchloride / water / 0.5 h / 20 °C View Scheme

: 67853-37-6
2-bromo-1-methoxy-3-nitrobenzene

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / PPh3 / Pd(dba)2 / toluene / 23.5 h / Heating 2: 89 percent / PPh3, CO / Pd(OAc)2 / acetonitrile / 20 h / 3040 Torr / Heating View Scheme
Multi-step reaction with 5 steps 1: 88 percent / iron / ethanol; acetic acid / 3.5 h / Heating 2: 72 percent / pyridine / 6 h / Ambient temperature 3: tetrakis(triphenylphosphine)palladium(0) / toluene / 36 h / Heating 4: 68 percent / bis(acetonitrile)palladium chloride, p-benzoquinone, lithium chloride / dimethylformamide / 28 h / 100 - 110 °C 5: 96 percent / 20percent aq. NaOH / methanol / 12 h / Heating View Scheme

Yield

Multi-step reaction with 2 steps
1: 89 percent / PPh3 / Pd(dba)2 / toluene / 23.5 h / Heating
2: 89 percent / PPh3, CO / Pd(OAc)2 / acetonitrile / 20 h / 3040 Torr / Heating
View Scheme

Multi-step reaction with 5 steps
1: 88 percent / iron / ethanol; acetic acid / 3.5 h / Heating
2: 72 percent / pyridine / 6 h / Ambient temperature
3: tetrakis(triphenylphosphine)palladium(0) / toluene / 36 h / Heating
4: 68 percent / bis(acetonitrile)palladium chloride, p-benzoquinone, lithium chloride / dimethylformamide / 28 h / 100 - 110 °C
5: 96 percent / 20percent aq. NaOH / methanol / 12 h / Heating
View Scheme

: 194869-14-2
1-tert-butoxycarbonyl-2-iodo-3-methoxyaniline

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / CuI, Pd(PPh3)2Cl2 / triethylamine / 24 h / 80 °C 2: 70 percent / t-BuOK / 2-methyl-propan-2-ol / 5 h / Heating View Scheme

: 555-03-3
3-nitroanisole

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 41 percent / tBuOK / dimethylformamide / 0.5 h / -20 - -10 °C 2: 96 percent / H2, acetic acid / Pd/C (10percent Pd) / ethanol / 2 h / 2280 Torr / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / -20 °C 2: acetic acid; palladium 10% on activated carbon; hydrogen / 12 h / 20 °C View Scheme

: 603-85-0
2-Amino-3-nitrophenol

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

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 1.) hydrobromic acid, sodium nitrite, 2.) coopper(I) bromide / 1.) water, 1,4-dioxane, 0 deg C, 15 min, 2.) a) 0 deg C, 15 min, b) 60 deg C, 15 min 2: sodium hydroxide, / aq. ethanol / 14 h / Ambient temperature 3: 88 percent / iron / ethanol; acetic acid / 3.5 h / Heating 4: 72 percent / pyridine / 6 h / Ambient temperature 5: tetrakis(triphenylphosphine)palladium(0) / toluene / 36 h / Heating 6: 68 percent / bis(acetonitrile)palladium chloride, p-benzoquinone, lithium chloride / dimethylformamide / 28 h / 100 - 110 °C 7: 96 percent / 20percent aq. NaOH / methanol / 12 h / Heating View Scheme

Yield

Multi-step reaction with 7 steps
1: 1.) hydrobromic acid, sodium nitrite, 2.) coopper(I) bromide / 1.) water, 1,4-dioxane, 0 deg C, 15 min, 2.) a) 0 deg C, 15 min, b) 60 deg C, 15 min
2: sodium hydroxide, / aq. ethanol / 14 h / Ambient temperature
3: 88 percent / iron / ethanol; acetic acid / 3.5 h / Heating
4: 72 percent / pyridine / 6 h / Ambient temperature
5: tetrakis(triphenylphosphine)palladium(0) / toluene / 36 h / Heating
6: 68 percent / bis(acetonitrile)palladium chloride, p-benzoquinone, lithium chloride / dimethylformamide / 28 h / 100 - 110 °C
7: 96 percent / 20percent aq. NaOH / methanol / 12 h / Heating
View Scheme

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

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

: 90734-97-7
4-methoxyindole-3-carboxaldehyde

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With N-chloro-succinimide; triphenylphosphine In tetrahydrofuran for 1h; Reflux; Stage #2: 4-methoxy-1H-indole In tetrahydrofuran for 1h; Reflux;	100%
Stage #1: N,N-dimethyl-formamide With N-chloro-succinimide; triphenylphosphine In tetrahydrofuran at 20℃; Reflux; Stage #2: 4-methoxy-1H-indole In tetrahydrofuran for 1h; Reflux;	100%
Stage #1: 4-methoxy-1H-indole; N,N-dimethyl-formamide With trichlorophosphate at 0 - 45℃; for 1.08333h; Inert atmosphere; Stage #2: With sodium hydroxide In water Inert atmosphere;	95%

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

: 7555-94-4
2,3-dihydro-4-methoxy-1H-indole

Conditions

Conditions	Yield
With sodium cyanoborohydride; acetic acid	100%
With sodium cyanoborohydride; acetic acid for 0.5h; Ambient temperature;	98%
With sodium cyanoborohydride; acetic acid at 20℃; for 0.833333h;	98%

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

: 1119-51-3
bromopentene

: 4-methoxy-1-(pent-4-en-1-yl)-1H-indole

Conditions

Conditions	Yield
Stage #1: 4-methoxy-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere; Stage #2: bromopentene In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	100%

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

: 74-88-4
methyl iodide

: 7556-35-6
4-methoxy-1-methyl-1H-indole

Conditions

Conditions	Yield
Stage #1: 4-methoxy-1H-indole With sodium hydride In acetonitrile at 0℃; for 0.5h; Stage #2: methyl iodide In acetonitrile at 0 - 20℃; for 16h;	99%
With sodium hydride In tetrahydrofuran at 0 - 20℃;	95%
With sodium hydride In tetrahydrofuran for 4h;	82%

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

: 33797-51-2
eschenmoser's salt

: 52335-75-8
(4-methoxy-1H-indol-3-ylmethyl)dimethylamine

Conditions

Conditions	Yield
In acetic acid; acetonitrile at 20℃; for 2h;	99%

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

: 1147550-11-5
ammonium thiocyanate

: 4-methoxy-3-thiocyanato-1H-indole

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 3h; Electrochemical reaction; Inert atmosphere;	99%
With copper(II) choride dihydrate; oxygen In ethanol at 20℃; for 24h; Irradiation;	98%
With iodine In methanol for 1h;	75%

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

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

: 1093759-59-1
4-methoxyindole-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With dmap In acetonitrile at 20℃; for 1h;	99%
With dmap; triethylamine In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; for 11h;	97%
With dmap In dichloromethane at 20℃; for 8h; Inert atmosphere;	95%

: 5153-67-3
nitrostyrene

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

: 1187817-63-5, 1236277-14-7
4-methoxy-3-(2-nitro-1-phenylethyl)-1H-indole

Conditions

Conditions	Yield
With pyrrolidinium 1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)ethanesulfonate at 50℃; for 12h; Friedel Crafts alkylation;	99%

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

: tert-butyl (1,3-dioxo-2-phenyl-2,3-dihydroisoquinolin-4(1H)-ylidene)carbamate

: (S)-tert-butyl (4-(4-methoxy-1H-indol-3-yl)-1,3-dioxo-2-phenyl-1,2,3,4-tetrahydroisoquinolin-4-yl)carbamate

Conditions

Conditions	Yield
With (11aR)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In toluene at 60℃; for 3h; enantioselective reaction;	99%

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

: 130-15-4
[1,4]naphthoquinone

: 2-(4-methoxy-1H-indol-3-yl)naphthalene-1,4-dione

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 0.0708333h; Flow reactor;	99%
With tris(pentafluorophenyl)borate In water at 60℃; for 2h;	52%

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

: 1033591-96-6
1-(1,3-benzothiazol-2-yl)-2,2,2-trifluoroethane-1,1-diol

: (R)-1-(benzo[d]thiazol-2-yl)-2,2,2-trifluoro-1-(4-methoxy-1H-indol-3-yl)ethan-1-ol

Conditions

Conditions	Yield
With (R)-6,6'-bis(2,4,6-triisopropylphenyl)-1,1'-spirobiindanyl-7,7'-diyl hydrogen phosphate In dichloromethane at 20℃; Friedel-Crafts Alkylation; Molecular sieve; enantioselective reaction;	99%

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

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1-(tert-Butyldimethylsilyl)-4-methoxyindole

Conditions

Conditions	Yield
Stage #1: 4-methoxy-1H-indole With n-butyllithium In tetrahydrofuran; hexane at -78 - -10℃; for 0.25h; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; hexane at 0℃; for 3h;	98%

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

: 5292-53-5
diethyl benzalmalonate

: (+)-ethyl 2-ethoxycarbonyl-3-[3-(4-methoxyindolyl)]-3-phenylpropanoate

Conditions

Conditions	Yield
With 1,2,2-tris[(4S)-4-iPr-4,5-dihydro-1,3-oxazol-2-yl]propane; copper(II) bis(trifluoromethanesulfonate) In 2-methyl-propan-1-ol at -25℃; for 50h; Friedel-Crafts alkylation of indoles;	98%

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

: 5292-53-5
diethyl benzalmalonate

: 458563-96-7
(S)-ethyl-2-ethoxycarbonyl-3-[3-(4-methoxyindolyl)]-3-phenyl-propanoate

Conditions

Conditions	Yield
Stage #1: diethyl benzalmalonate With (3aR,8aS)-2-(3-(3,5-di-tert-butylphenyl)-2,2-bis((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)propyl)-8,8a-dihydro-3aH-indeno[1,2-d]oxazole; copper(II) bis(trifluoromethanesulfonate) In iso-butanol at -25℃; for 0.25h; Friedel Crafts alkylation; Stage #2: 4-methoxy-1H-indole In iso-butanol at -25℃; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;	98%
1,1'-bis(4-(S)-isopropyl-1,3-oxazolin-2-yl)ethane*Cu(OTf)2 In water; iso-butanol at -15 - 0℃;	90%

Yield

Stage #1: diethyl benzalmalonate With (3aR,8aS)-2-(3-(3,5-di-tert-butylphenyl)-2,2-bis((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)propyl)-8,8a-dihydro-3aH-indeno[1,2-d]oxazole; copper(II) bis(trifluoromethanesulfonate) In iso-butanol at -25℃; for 0.25h; Friedel Crafts alkylation;
Stage #2: 4-methoxy-1H-indole In iso-butanol at -25℃; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;

98%

1,1'-bis(4-(S)-isopropyl-1,3-oxazolin-2-yl)ethane*Cu(OTf)2 In water; iso-butanol at -15 - 0℃;

90%

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

: sodium 1-(tert-butoxycarbonyl) azetidine-3-sulfinate

: tert-butyl 3-((4-methoxy-1H-indol-2-yl)sulfonyl)azetidine-1-carboxylate

Conditions

Conditions	Yield
With iodine In methanol at 20℃; for 24h; regioselective reaction;	98%

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

: 421-83-0
trifluoromethane sulfonyl chloride

: 4-methoxy-3-((trifluoromethyl)thio)-1H-indole

Conditions

Conditions	Yield
With triphenylphosphine; sodium iodide In acetonitrile at 60℃; for 1.5h; Schlenk technique; Inert atmosphere;	98%
With phosphonic acid diethyl ester In acetonitrile at 90℃; for 10h;	90%
With 1,2,2,3,4,4-hexamethylphosphetane 1-oxide; phenylsilane In 1,4-dioxane at 40℃; for 1h; Schlenk technique; Sealed tube; Inert atmosphere;	89%

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

: S-(difluoromethyl) benzenesulfonothioate

: 3-((difluoromethyl)thio)-4-methoxy-1H-indole

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In acetonitrile at 20℃; for 16h; Inert atmosphere; Irradiation; regioselective reaction;	98%

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

: 2905-21-7
2-fluorobenzenesulfonyl chloride

: 530116-16-6
C15H12FNO3S

Conditions

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water at 20℃;	97%

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

: 2923-28-6
silver trifluoromethanesulfonate

: 75586-32-2
2-phenylethynylbenzaldehyde p-toluenesulphonylhydrazone

: 1198746-32-5
1-(4-methoxyindol-3-yl)-2-amino-3-phenylisoquinolinium triflate

Conditions

Conditions	Yield
With dysprosium(III) trifluoromethanesulfonate In 1,2-dichloro-ethane at 70℃; Inert atmosphere;	97%

...Expand

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

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

: (R)-ethyl 3,3,3-trifluoro-2-hydroxy-2-(4-methoxy-1H-indol-3-yl)-propanoate

Conditions

Conditions	Yield
Stage #1: 4-methoxy-1H-indole With C33H52N4O4; zinc trifluoromethanesulfonate In dichloromethane at 35℃; for 0.5h; Stage #2: ethyl-3,3,3-trifluoropyruvate In dichloromethane at 0℃; for 0.5h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;	97%

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

: 776-76-1
methyldiphenylsilane

: 1343516-70-0
4-methoxy-1-(methyldiphenylsilyl)-1H-indole

Conditions

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium In toluene at 120℃; for 12h; Schlenk technique; Inert atmosphere;	97%
With pyridine; zinc trifluoromethanesulfonate In propiononitrile at 80℃; for 15h; Inert atmosphere;	94%

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

: 34157-83-0
celastrol

: (2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(4-methoxy-1H-indol-3-yl)-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions

Conditions	Yield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;	97%

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

: 94-41-7
benzalacetophenone

: 3-(4-methoxy-1H-indol-3-yl)-1,3-diphenylpropan-1-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile at 50℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;	97%

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

: 920-66-1
1,1,1,3',3',3'-hexafluoro-propanol

: 1,1,1,3,3,3-hexafluoro-2-(4-methoxy-1H-indol-3-yl)propan-2-ol

Conditions

Conditions	Yield
With copper diacetate; 4,4'-di-tert-butyl-2,2'-bipyridine at 90℃; for 24h; Schlenk technique; regioselective reaction;	97%

: 5153-67-3
nitrostyrene

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

: 4-methoxy-3-(2-nitro-1-phenylethyl)-1H-indole

Conditions

Conditions	Yield
With piperidine; 2-(((S)-1-hydroxy-1,1,3-triphenylpropan-2-ylimino)methyl)-6-chlorophenol; zinc trifluoromethanesulfonate In toluene at 20℃; for 24h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;	96%

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

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

: (S)-ethyl 3,3,3-trifluoro-2-hydroxy-2-(4-methoxy-1H-indol-3-yl)-propanoate

Conditions

Conditions	Yield
Stage #1: 4-methoxy-1H-indole With C33H52N4O4; zinc trifluoromethanesulfonate In dichloromethane at 35℃; for 0.5h; Stage #2: ethyl-3,3,3-trifluoropyruvate In dichloromethane at 0℃; for 0.5h; Friedel Crafts alkylation; optical yield given as %ee; enantioselective reaction;	96%

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

: 459-57-4
4-fluorobenzaldehyde

: di-(4-methoxy-1H-indol-3-yl)-4-fluorophenylmethane

Conditions

Conditions	Yield
With sulfuric acid In water at 20℃; for 0.0833333h; Green chemistry;	96%

4-Methoxyindole Specification

The 4-Methoxyindole, with the CAS registry number 4837-90-5, has the systematic name of 4-methoxy-1H-indole. And the molecular formula of this chemical is C₉H₉NO. It is a kind of light brown to grey crystalline powder which is sensitive to light, and it belongs to the folllowing product categories: Blocks; IndolesOxindoles; Indoles and derivatives; Pyrroles & Indoles; Indoline & Oxindole; Indole Series; Indoles; Simple Indoles; Pyrroles & Indoles; Building Blocks; Heterocyclic Building Blockss. What's more, it is used as medicine intermediate.

The physical properties of 4-Methoxyindole are as following: (1)ACD/LogP: 2.06; (2)# of Rule of 5 Violations: 0 ; (3)#H bond acceptors: 2; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 1; (6)Polar Surface Area: 14.16 Å²; (7)Index of Refraction: 1.637; (8)Molar Refractivity: 45.2 cm³; (9)Molar Volume: 125.8 cm³; (10)Polarizability: 17.92×10^-24cm³; (11)Surface Tension: 45.7 dyne/cm; (12)Density: 1.169 g/cm³; (13)Flash Point: 109.2 °C; (14)Enthalpy of Vaporization: 52.56 kJ/mol; (15)Boiling Point: 306.9 °C at 760 mmHg; (16)Vapour Pressure: 0.00136 mmHg at 25°C.

Uses of 4-Methoxyindole: It can react with triethoxymethane to produce 3-(4-Methoxyindolin-2-yl)-4-methoxyindole. This reaction will need reagent Cl₃CCOOH, and the solvent CH₂Cl₂. The reaction time is 25 minutes with ambient temperature, and the yield is about 60%.

4-Methoxyindole can react with triethoxymethane to produce 3-(4-Methoxyindolin-2-yl)-4-methoxyindole

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Avoid contact with skin and eyes; Wear suitable protective clothing; In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O(c1cccc2c1ccn2)C
(2)InChI: InChI=1/C9H9NO/c1-11-9-4-2-3-8-7(9)5-6-10-8/h2-6,10H,1H3
(3)InChIKey: LUNOXNMCFPFPMO-UHFFFAOYAZ

Product Name

4-Methoxyindole

Synthetic route

4-Methoxyindole Specification

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