5-Methoxyindole-2-carboxylic acid

Base Information

• Chemical Name: 5-Methoxyindole-2-carboxylic acid
• CAS No.: 4382-54-1
• Molecular Formula: C10H9NO3
• Molecular Weight: 191.186
• Hs Code.: 29339900
• European Community (EC) Number: 224-487-6
• NSC Number: 30927
• UNII: AFK8L54HA2
• DSSTox Substance ID: DTXSID40195944
• Nikkaji Number: J41.036E
• Wikidata: Q72490085
• Metabolomics Workbench ID: 128805
• ChEMBL ID: CHEMBL23961
• Mol file: 4382-54-1.mol

Synonyms:5-methoxyindole-2-carboxylic acid

Chemical Property of 5-Methoxyindole-2-carboxylic acid

Chemical Property:

• Appearance/Colour: light yellow to brownish powder
• Vapor Pressure: 8.54E-09mmHg at 25°C
• Melting Point: 199-201 °C
• Refractive Index: 1.5310 (estimate)
• Boiling Point: 447.6 °C at 760 mmHg
• PKA: 4.38±0.30(Predicted)
• Flash Point: 224.5 °C
• PSA: 62.32000
• Density: 1.381 g/cm³
• LogP: 1.87470
• Storage Temp.: Refrigerator
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 191.058243149
• Heavy Atom Count: 14
• Complexity: 231

Purity/Quality:

99% ^*data from raw suppliers

5-Methoxyindole-2-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)NC(=C2)C(=O)O
• Uses: Reactant for preparation of:? ;Anticancer agents1? ;A fluorescent small molecule probe for in vivo lipid imaging2? ;Indoleamine 2,3-dioxygenase (IDO) inhibitors3? ;Selective Dopamine D3 receptor ligands4? ;5-HT4 receptor ligands5? ;Inhibitors of Mycobacterium tuberculosis pantothenate synthetase6? ;Hypoxia selective cytotoxins7? ;Potent antitumor bifunctional DNA alkylating agents8 5-Methoxyindole-2-carboxylic Acid is a very useful synthetic intermediate. It is a reactant used to prepare anticancer agents, Indoleamine 2,3-dioxygenase (IDO) inhibitors, and potent antitumor bifunctional DNA alkylating agents. Reactant for preparation of:Anticancer agentsA fluorescent small molecule probe for in vivo lipid imagingIndoleamine 2,3-dioxygenase (IDO) inhibitorsSelective Dopamine D3 receptor ligands5-HT4 receptor ligandsInhibitors of Mycobacterium tuberculosis pantothenate synthetaseHypoxia selective cytotoxinsPotent antitumor bifunctional DNA alkylating agents

Technology Process of 5-Methoxyindole-2-carboxylic acid

There total 21 articles about 5-Methoxyindole-2-carboxylic 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: 99.0%

methyl 5-methoxyindole-2-carboxylate (67929-86-6) → 5-methoxy-1H-indole-2-carboxylic acid (4382-54-1)

Guidance literature:

With sodium hydroxide; Heating;

DOI:10.1021/jm0493616

Reference yield: 99.0%

→ 5-methoxy-1H-indole-2-carboxylic acid (4382-54-1)

Guidance literature:

Reference yield: 97.0%

ethyl 5-methoxy-1H-indole-2-carboxylate (4792-58-9) → 5-methoxy-1H-indole-2-carboxylic acid (4382-54-1)

Guidance literature:

With sodium hydroxide; In ethanol; Heating;

DOI:10.1016/0223-5234(90)90209-L

upstream raw materials:

ethyl 5-methoxy-1H-indole-2-carboxylate

(5-methoxy-2-nitro-phenyl)-pyruvic acid

methyl 5-methoxyindole-2-carboxylate

3-methoxy-benzaldehyde

Downstream raw materials:

5-methoxylindole

5-methoxy-1-phenyl-1H-indole-2-carboxylic acid

ethyl 5-methoxy-1H-indole-2-carboxylate

(5-Benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indol-3-yl)-(5-methoxy-1H-indol-2-yl)-methanone

Refernces

• 1、 -. "Synthesis method of indole-2-carboxylic acid and derivative thereof". Paragraph 0043; 0050-0053. . Retrieved 2019/02/21.
• 2、 -. "1H-indole-2-carboxamide derivative and preparation method and applications thereof". Paragraph 0125; 0126; 0129; 0130. . Retrieved 2018/12/05.