5-Methoxyindole-3-acetic acid

Base Information

• Chemical Name: 5-Methoxyindole-3-acetic acid
• CAS No.: 3471-31-6
• Deprecated CAS: 110885-75-1
• Molecular Formula: C11H11NO3
• Molecular Weight: 205.213
• Hs Code.: 29339900
• European Community (EC) Number: 222-438-3
• UNII: MSN7CK6ETH
• DSSTox Substance ID: DTXSID70188268
• Nikkaji Number: J139.625K
• Wikidata: Q6172526
• Metabolomics Workbench ID: 38467
• ChEMBL ID: CHEMBL85433
• Mol file: 3471-31-6.mol

Synonyms:5-methoxyindole-3-acetic acid;5-methoxyindoleacetic acid

Chemical Property of 5-Methoxyindole-3-acetic acid

Chemical Property:

• Appearance/Colour: Off-white to slightly beige crystalline powder
• Vapor Pressure: 9.85E-09mmHg at 25°C
• Melting Point: 145-148 °C (dec.)(lit.)
• Refractive Index: 1.5130 (estimate)
• Boiling Point: 445.9°C at 760 mmHg
• PKA: 4.52±0.30(Predicted)
• Flash Point: 223.5°C
• PSA: 62.32000
• Density: 1.2235 (rough estimate)
• LogP: 1.80360
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: insoluble
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 205.07389321
• Heavy Atom Count: 15
• Complexity: 244

Purity/Quality:

99% ^*data from raw suppliers

5-Methoxyindole-3-acetic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)NC=C2CC(=O)O
• Uses: Reactant for preparation of aryloxybenzothiazoles as inhibitors of NO production 1 Reactant for preparation of transcription inhibitors of novel Gli1 as antitumor agents Reactant for preparation of indole derivatives as NR2B/NMDA receptor antagonists 2 Reactant for preparation of indolyl esters and amides related to indomethacin as selective COX-2 inhibitors 3 Reactant for preparation of quinoline salicylic acid series of P-selectin antagonists 4 Reactant for preparation of prostaglandin D2 receptor antagonists. 5-Methoxyindole-3-acetic Acid is a chemical reagent used in the analysis of the physiological properties of auxins. Reactant for preparation of aryloxybenzothiazoles as inhibitors of NO productionReactant for preparation of transcription inhibitors of novel Gli1 as antitumor agentsReactant for preparation of indole derivatives as NR2B/NMDA receptor antagonistsReactant for preparation of indolyl esters and amides related to indomethacin as selective COX-2 inhibitorsReactant for preparation of quinoline salicylic acid series of P-selectin antagonistsReactant for preparation of prostaglandin D2 receptor antagonists

Technology Process of 5-Methoxyindole-3-acetic acid

There total 17 articles about 5-Methoxyindole-3-acetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(5-methoxy-1H-indol-3-yl)acetic acid methyl ester (23304-48-5) → 5-methoxy-1H-indole-3-acetic acid (3471-31-6,142396-09-6)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1016/j.phytochem.2007.04.030

Reference yield: 85.2%

1,3-diacetyl-5-methoxyindole → 5-methoxy-1H-indole-3-acetic acid (3471-31-6,142396-09-6)

Guidance literature:

1,3-diacetyl-5-methoxyindole; With morpholine; sulfur; at 120 ℃; for 6h;

With sodium hydroxide; In ethanol; for 4h; Reflux;

Reference yield: 80.0%

→ 5-methoxy-1H-indole-3-acetic acid (3471-31-6,142396-09-6)

Guidance literature:

With morpholine; sulfur; at 120 ℃; for 8h;

With sodium hydroxide; In ethanol; for 4h; Reflux;

upstream raw materials:

5-methoxyindole-3-acetonitrile

(5-methoxy-1H-indol-3-yl)acetic acid ethyl ester

(5-methoxy-1H-indol-3-yl)acetic acid methyl ester

5-methoxylindole

Downstream raw materials:

5-Hydroxyindole-3-acetic acid

(5-methoxy-1H-indol-3-yl)acetic acid ethyl ester

N,O-Bis(trimethylsilyl)-5-methoxyindolyl-3-essigsaeureester

(5-methoxy-1H-indol-3-yl)acetic acid methyl ester

Refernces

• 1、 -. "Agent for Preventing or Ameliorating Hearing Impairment". Paragraph 0093; 0094; 0261-0262. . Retrieved 2019/08/02.
• 2、 -. "Aryl [a] indole [2,3 - the g] and quinolizine compound, preparation method thereof, pharmaceutical compositions and uses thereof". . . Retrieved 2017/01/17.