ChemicalBook > CAS DataBase List > 4-Methoxyindole

4-Methoxyindole

Product Name
4-Methoxyindole
CAS No.
4837-90-5
Chemical Name
4-Methoxyindole
Synonyms
4-METHOXY-1H-INDOLE;AKOS JY2082619;4-METHOXYINDOLE;4-METHOXYLINDOLE;Methoxyindole,98%;Indole, 4-methoxy-;4-Methoxyindole>4-Methoxyindole,99%;4-Methoxyindole 99%;4-METHOXYINDOLE 98+%
CBNumber
CB5273308
Molecular Formula
C9H9NO
Formula Weight
147.17
MOL File
4837-90-5.mol
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4-Methoxyindole Property

Melting point:
69-70 °C (lit.)
Boiling point:
181-183 °C/24 mmHg (lit.)
Density 
1.1135 (rough estimate)
refractive index 
1.5310 (estimate)
Flash point:
181-183°C/24mm
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
ethanol: soluble50mg/mL, clear, faintly yellow
pka
17.22±0.30(Predicted)
form 
Crystalline Powder and/or Chunks
color 
White
Sensitive 
Light Sensitive
BRN 
122456
InChIKey
LUNOXNMCFPFPMO-UHFFFAOYSA-N
LogP
2.060 (est)
CAS DataBase Reference
4837-90-5(CAS DataBase Reference)
NIST Chemistry Reference
1H-Indole, 4-methoxy-(4837-90-5)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-24/25
WGK Germany 
3
Hazard Note 
Irritant/Keep Cold
HazardClass 
KEEP COLD, LIGHT SENSITIVE
HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
246298
Product name
4-Methoxyindole
Purity
99%
Packaging
1g
Price
$72.6
Updated
2024/03/01
TCI Chemical
Product number
M1250
Product name
4-Methoxyindole
Purity
>98.0%(GC)
Packaging
1g
Price
$29
Updated
2024/03/01
TCI Chemical
Product number
M1250
Product name
4-Methoxyindole
Purity
>98.0%(GC)
Packaging
5g
Price
$82
Updated
2024/03/01
Alfa Aesar
Product number
L19069
Product name
4-Methoxyindole, 99%
Packaging
1g
Price
$142.65
Updated
2024/03/01
Alfa Aesar
Product number
L19069
Product name
4-Methoxyindole, 99%
Packaging
5g
Price
$527
Updated
2021/12/16
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4-Methoxyindole Chemical Properties,Usage,Production

Chemical Properties

light brown to grey crystalline powder

Uses

4-Methoxyindole is a reactant for alpha-ethyltryptamines as dual dopamine-serotonin releasers.

Application

Reactant for preparation of:
GABA analogs
Sodium-Dependent Glucose Co-transporter 2 (SGLT2) Inhibitors for the Management of Hyperglycemia in Diabetes
Anticancer agents
Integrase strand-transfer inhibitors (INSTIs)
Inhibitor of Proliferation of Colon Cancer Cells
Isomeridianin G as GSK-3? inhibitors
HIV-1 integrase inhibitors
Inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)
4-Methoxyindole was used for comparing the complexation reaction of β-cyclodextrin (β-CD) with pindolol using reversed-phase liquid chromatography.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 1499, 1987 DOI: 10.1002/jhet.5570240602

Biotechnological Applications

4-Methoxyindole is used in a variety of preparation procedures. It is a reactant involved in the synthesis of GABA analogs, HIV-1 integrase inhibitors, anticancer agents, sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors, integrase strand-transfer inhibitors (INSTIs), and isomeridianin G. Additionally, it is used in reverse-phase liquid chromatography analysis of the reaction of β-cyclodextrin and pindolol.

Synthesis

Step1 :1-[(E)-2-(2-methoxy-6-nitrophenyl)vinyl]pyrrolidine: To a solution of 10 g of 1-methoxy-2-methy3-nitrobenzene in 100 ml of DMF are added 8.74 ml of N,N-dimethylformamide dimethyl acetal and 5.44 ml of pyrrolidine, and the mixture is then refluxed for 3 hours. The mixture is concentrated to half its volume under vacuum, the remaining mixture is poured into ether/water and extracted with ether, the organic phase is washed with saturated NaCl solution and dried over MgSO4 , and the solvent is evaporated off under vacuum. 1-[(E)-2-(2-methoxy-6-nitrophenyl)vinyl]pyrrolidine; yield 14.6 g.
Stpe 2 : synthesis of 4-Methoxyindole, A suspension of 150 ml of zinc powder in 500 ml of 0.5N HCl is stirred for 1 hour at room temperature. The suspension is ded by suction, washed with water to neutral pH, with anhydrous EtOH and then with ether, and dried. To a solution of 10 g of the compound from the preceding step in 46 ml of acetic acid are added, portionwise, 31.6 g of activated zinc, while keeping the temperature between 20 and 30°C using an ice bath. The reaction mixture is stirred at room temperature for 30 minutes, and is filtered. The filtrate is extracted with EtOAc, the organic phase is washed with NaHCO3 solution and with saturated NaCl solution, and dried over MgSO4 , and the solvent is evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with a cyclohexane/EtOAc mixture in a gradient of from (98/2 v/v) to (95/5 v/v). 4-Methoxy- 1H-indole; yield 1.6 g.

4-Methoxyindole Preparation Products And Raw materials

Raw materials

Preparation Products

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4-Methoxyindole Suppliers

GLR Innovations
Tel
+91 9891111994
Email
info@glrgroup.in
Country
India
ProdList
4535
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58
TCI Chemicals (India) Pvt. Ltd.
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--
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Email
sales-in@tcichemicals.com
Country
India
ProdList
6768
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58
Chaturya Biotech (Tanuj Life Sciences)
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info@chaturyabiotech.com
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India
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398
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Clearsynth Labs
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fo@clearsynth.com
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ProdList
3887
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Ramkishore Chemical Company Pvt. Ltd.
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India
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SNR Pharma
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India
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Aravali Pharma & Lifesciences
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mail@aravalipharma.com
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Oceanic Pharmachem Pvt., Ltd. (OPPL)
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A.J Chemicals
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sales@ajchem.in
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CHEMSWORTH
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Dhruvtara Chemicals Pvt. Ltd.
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info@dhruvtarachemicals.com
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View Lastest Price from 4-Methoxyindole manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
4-Methoxyindole 4837-90-5
Price
US $0.00-0.00/KG
Min. Order
5mg
Purity
99%HPLC
Supply Ability
2000tons
Release date
2020-01-06
Henan Bao Enluo International TradeCo.,LTD
Product
4-Methoxyindole 4837-90-5
Price
US $20.00/kg
Min. Order
1kg
Purity
99.99%
Supply Ability
50000tons
Release date
2023-08-15
Henan Aochuang Chemical Co.,Ltd.
Product
4-Methoxyindole 4837-90-5
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1ton
Release date
2022-10-12

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