5-Methoxy-2-methyl-3-indoleacetic acid

Base Information

• Chemical Name: 5-Methoxy-2-methyl-3-indoleacetic acid
• CAS No.: 2882-15-7
• Molecular Formula: C12H13NO3
• Molecular Weight: 219.24
• Hs Code.: 29349990
• European Community (EC) Number: 220-734-7
• NSC Number: 97026
• UNII: KY9AD0AQM0
• DSSTox Substance ID: DTXSID00183009
• Nikkaji Number: J306.806D
• Wikidata: Q72490481
• Metabolomics Workbench ID: 42552
• ChEMBL ID: CHEMBL1058
• Mol file: 2882-15-7.mol

Synonyms:(des-4-chlorobenzoyl)indomethacin;5-methoxy-2-methyl-3-indoleacetic acid;5-methoxy-methylindoleacetic acid;DBI;deschlorobenzoylindomethacin

Chemical Property of 5-Methoxy-2-methyl-3-indoleacetic acid

Chemical Property:

• Appearance/Colour: slightly yellow fine crystalline powder
• Vapor Pressure: 6.83E-09mmHg at 25°C
• Melting Point: 161-163 °C(lit.)
• Refractive Index: 1.5270 (estimate)
• Boiling Point: 450.2 °C at 760 mmHg
• PKA: 4.22±0.30(Predicted)
• Flash Point: 226.1 °C
• PSA: 62.32000
• Density: 1.292g/cm³
• LogP: 2.11200
• Storage Temp.: 2-8°C
• Solubility.: methanol: soluble
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 219.08954328
• Heavy Atom Count: 16
• Complexity: 269

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-DeschlorobenzoylIndomethacin ^*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: CC1=C(C2=C(N1)C=CC(=C2)OC)CC(=O)O
• Uses: A metabolite of Indomethacin. Reactant for preparation of antimalarial agentsReactant for preparation of ndomethacin analogs as cyclooxygenase and lipoxygenase inhibitors with antiinflammatory activityReactant for preparation of [123I]-indomethacin derivatives as COX-2 targeted imaging agentsReactant for preparation of histone deacetylase inhibitorsReactant for preparation of 2,N6,5′-substituted adenosine derivatives as ligands for A2B adenosine receptorReactant for preparation of prostaglandin D2 receptor antagonist 5-Methoxy-2-methyl-3-indoleacetic acid was used for quantitative determination of indomethacin and its major impurities in suppository and capsule formulations by HPLC. 5-Methoxy-2-methyl-3-indoleacetic acid was used in a study to develop fast, sensitive and simultaneous determination of metabolites of serotonin using liquid chromatography with mass spectrometric detection.

Technology Process of 5-Methoxy-2-methyl-3-indoleacetic acid

There total 36 articles about 5-Methoxy-2-methyl-3-indoleacetic 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: 98.0%

ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate (17536-38-8) → 5-Methoxy-2-methylindole-3-acetic acid (2882-15-7)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 20 ℃; for 3h;

DOI:10.1039/c9md00173e

Reference yield: 82.0%

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid (53-86-1) → 5-Methoxy-2-methylindole-3-acetic acid (2882-15-7)

Guidance literature:

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid; With sodium methylate; In methanol; for 72h; Inert atmosphere;

With hydrogenchloride; In water; pH=Ca. 1; Inert atmosphere;

DOI:10.1016/j.bmc.2012.05.063

Reference yield: 74.0%

levulinic acid (123-76-2) + 4-Methoxyphenylhydrazine (3471-32-7) → 5-Methoxy-2-methylindole-3-acetic acid (2882-15-7)

Guidance literature:

With acetic acid; for 4h; Reflux;

DOI:10.3184/174751916X14737735069962

upstream raw materials:

4-(4-methoxy-phenylhydrazono)-valeric acid methyl ester

(5-methoxy-2-methyl-1H-indol-3-yl)-acetonitrile

ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate

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

Downstream raw materials:

2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide

ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate

(1-Benzyl-5-methoxy-2-methyl-1H-indol-3-yl)-acetic acid benzyl ester

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

Refernces

• 1、 Xu, Guangsen,Liu, Tingting,Zhou, Yi,Yang, Xinying,Fang, Hao. "1-Phenyl-1H-indole derivatives as a new class of Bcl-2/Mcl-1 dual inhibitors: Design, synthesis, and preliminary biological evaluation". . p. 5548 - 5556. Retrieved 2017.
• 2、 Ji, Jing,Li, Jiaojiao,Li, Zhengfu,Xu, Ruibo. "Indole compounds with: N-ethyl morpholine moieties as CB2 receptor agonists for anti-inflammatory management of pain: Synthesis and biological evaluation". supporting information. p. 1935 - 1947. Retrieved 2019/11/20.
• 3、 Ning, Xiao-Shan,Liang, Xin,Hu, Kang-Fei,Yao, Chuan-Zhi,Qu, Jian-Ping,Kang, Yan-Biao. "Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis". supporting information. p. 1590 - 1594. Retrieved 2018/04/30.