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6-Methoxyindole
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Name

6-Methoxyindole

 EINECS 221-689-6
CAS No. 3189-13-7 Density 1.169 g/cm3
PSA 25.02000 LogP 2.17650
Solubility N/A 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 N/A Appearance white shiny crystals
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 3189-13-7 (6-Methoxyindole) Hazard Symbols IrritantXi
Synonyms

6-Methoxy-1H-indole;1H-Indole, 6-methoxy-;Indole, 6-methoxy-;6-Methoxy-indole;

Article Data 57

6-Methoxyindole Synthetic route

16732-73-3

6-Methoxyindole-2-carboxylic acid

3189-13-7

6-methoxylindole

Conditions
ConditionsYield
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
ConditionsYield
With sodium hydroxide In ethanol for 1h; Heating;98%
107734-26-9

6-methoxy-N-(toluenesulfonyl)indole

3189-13-7

6-methoxylindole

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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;
7556-47-0

6-methoxy-2,3-dihydro-1H-indole

3189-13-7

6-methoxylindole

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

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

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