5-Hydroxyindomethacin

Base Information

• Chemical Name: 5-Hydroxyindomethacin
• CAS No.: 2504-32-7
• Molecular Formula: C18H14 Cl N O4
• Molecular Weight: 343.766
• UNII: K89VS3UAD8
• DSSTox Substance ID: DTXSID60179746
• Nikkaji Number: J429.110G
• ChEMBL ID: CHEMBL800
• Mol file: 2504-32-7.mol

Synonyms:5-hydroxyindomethacin;5-hydroxyindomethacin sulfate(1:1);desmethyl-indomethacin;O-desmethylindomethacin

Chemical Property of 5-Hydroxyindomethacin

Chemical Property:

• Vapor Pressure: 1.37E-11mmHg at 25°C
• Melting Point: 217-219?C
• Boiling Point: 518.8°Cat760mmHg
• PKA: 3.98±0.30(Predicted)
• Flash Point: 267.6°C
• PSA: 79.53000
• Density: 1.4g/cm³
• LogP: 3.62430
• Storage Temp.: -20°C Freezer
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 343.0611356
• Heavy Atom Count: 24
• Complexity: 491

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

O-Desmethyl Indomethacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(N1C(=O)C3=CC=C(C=C3)Cl)C=CC(=C2)O)CC(=O)O
• Uses: The major metabolite of Indomethacin.

Technology Process of 5-Hydroxyindomethacin

There total 9 articles about 5-Hydroxyindomethacin 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: 88.0%

[1-(4-chloro-benzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]-acetic acid tert-butyl ester (346424-36-0) → O-Desmethyl-Indomethacin (2504-32-7)

Guidance literature:

With trifluoroacetic acid; for 1h;

DOI:10.1021/jm000483h

Reference yield: 87.0%

acemetacin tert-butyl ester (75302-98-6) → O-Desmethyl-Indomethacin (2504-32-7)

Guidance literature:

With iodine; aluminium; In acetonitrile; at 80 ℃; for 18h; chemoselective reaction;

DOI:10.1016/j.tetlet.2018.03.010

Reference yield: 72.0%

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid (53-86-1) → O-Desmethyl-Indomethacin (2504-32-7)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃;

DOI:10.1021/jm0611861

upstream raw materials:

[1-(4-chloro-benzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]-acetic acid tert-butyl ester

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

levulinic acid t-butyl ester

4-benzyloxyphenylhydrazine hydrochloride

Downstream raw materials:

N-3-methoxypropyl-(1-p-chlorobenzoyl-5-hydroxy-2-methylindole)-3-acetamide

N-2-ethoxyethyl-(1-p-chlorobenzoyl-5-hydroxy-2-methylindole)-3-acetamide

C₂₅H₂₀ClNO₄

methyl [1-(4-chlorobenzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]acetate