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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
Molecular Weight:
147.17
MDL Number:
MFCD00009737
MOL File:
4837-90-5.mol
MSDS File:
SDS
Last updated:2023-08-15 17:37:19

4-Methoxyindole Properties

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
form Crystalline Powder and/or Chunks
pka 17.22±0.30(Predicted)
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)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
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
NFPA 704
1
0 0

4-Methoxyindole price More Price(42)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 246298 4-Methoxyindole 99% 4837-90-5 1g $72.6 2024-03-01 Buy
TCI Chemical M1250 4-Methoxyindole >98.0%(GC) 4837-90-5 1g $29 2024-03-01 Buy
TCI Chemical M1250 4-Methoxyindole >98.0%(GC) 4837-90-5 5g $82 2024-03-01 Buy
Alfa Aesar L19069 4-Methoxyindole, 99% 4837-90-5 1g $142.65 2024-03-01 Buy
Alfa Aesar L19069 4-Methoxyindole, 99% 4837-90-5 5g $527 2021-12-16 Buy
Product number Packaging Price Buy
246298 1g $72.6 Buy
M1250 1g $29 Buy
M1250 5g $82 Buy
L19069 1g $142.65 Buy
L19069 5g $527 Buy

4-Methoxyindole Chemical Properties,Uses,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.
synthesis of 4-Methoxyindole

103260-65-7
4837-90-5
Synthesis of 4-Methoxyindole from 4-Methoxy-1H-indole-2-carboxylic acid
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View Lastest Price from 4-Methoxyindole manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
4-Methoxyindole pictures 2024-11-05 4-Methoxyindole
4837-90-5
US $0.00-0.00 / KG 5mg 99%HPLC 2000tons Shaanxi Dideu Medichem Co. Ltd
4-Methoxyindole pictures 2023-08-15 4-Methoxyindole
4837-90-5
US $20.00 / kg 1kg 99.99% 50000tons Henan Bao Enluo International TradeCo.,LTD
4-Methoxyindole pictures 2022-10-13 4-Methoxyindole
4837-90-5
US $0.00-0.00 / KG 1KG 98% 1ton Henan Aochuang Chemical Co.,Ltd.
  • 4-Methoxyindole pictures
  • 4-Methoxyindole
    4837-90-5
  • US $0.00-0.00 / KG
  • 99%HPLC
  • Shaanxi Dideu Medichem Co. Ltd
  • 4-Methoxyindole pictures
  • 4-Methoxyindole
    4837-90-5
  • US $20.00 / kg
  • 99.99%
  • Henan Bao Enluo International TradeCo.,LTD
  • 4-Methoxyindole pictures
  • 4-Methoxyindole
    4837-90-5
  • US $0.00-0.00 / KG
  • 98%
  • Henan Aochuang Chemical Co.,Ltd.
4-METHOXYLINDOLE 4-METHOXYINDOLE AKOS JY2082619 Methoxyindole,98% 4-Methoxyindole,99% 4-METHOXYLINDOLE 98% 4-METHOXYINDOLE 98+% 4-methoxy-1H-indole(SALTDATA: FREE) 1H-Indole, 4-Methoxy- 4-Methoxy-1H-indole 98% 4-Methoxyindole 99% 4-Methoxy-1H-indole98% 4-methoxy-1H-indole, 4-methoxy-indole, methoxy-1H-indole, 4-methoxy indole, 4-methoxylindole, 5-methoxylindole, 4-methoxyindole 1H-INDOL-4-YL METHYL ETHER Indole, 4-methoxy- 4-Methoxyindole> TIANFUCHEM-4-Methoxyindole 4-Methoxyindole in stock Factory 4-Methoxyindole, 98%, for synthesis 4-METHOXY-1H-INDOLE 4837-90-5 548-37-90-5 4387-90-5 Heterocyclic Building Blocks Simple Indoles Indoles Building Blocks Heterocycle-Indole series Simple Indoles Pyrroles & Indoles Building Blocks Heterocyclic Building Blocks Indoles Indoles and derivatives blocks IndolesOxindoles Pyrroles & Indoles Indoline & Oxindole Indole Series