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4-Methoxyindole

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Name

4-Methoxyindole

EINECS -0
CAS No. 4837-90-5 Density 1.169 g/cm3
PSA 25.02000 LogP 2.17650
Solubility N/A 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 N/A Appearance light brown to grey crystalline powder
Safety 26-36-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 4837-90-5 (4-Methoxyindole) Hazard Symbols IrritantXi
Synonyms

4-methoxy-1H-indole;1H-Indole, 4-methoxy-;4-Methoxy Indole;4-Methoxy-indole;

Article Data 45

4-Methoxyindole Synthetic route

103260-65-7

4-methoxy-1H-indole-2-carboxylic acid

4837-90-5

4-methoxy-1H-indole

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

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

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