5-Fluoroindole-2-carboxylic acid

Base Information

• Chemical Name: 5-Fluoroindole-2-carboxylic acid
• CAS No.: 399-76-8
• Molecular Formula: C9H6FNO2
• Molecular Weight: 179.151
• Hs Code.: 29339900
• European Community (EC) Number: 206-919-5
• UNII: LFV2Z936CQ
• DSSTox Substance ID: DTXSID10192945
• Nikkaji Number: J149.573I
• Wikidata: Q27190893
• ChEMBL ID: CHEMBL23507
• Mol file: 399-76-8.mol

Synonyms:5-fluoroindole-2-carboxylic acid

Chemical Property of 5-Fluoroindole-2-carboxylic acid

Chemical Property:

• Appearance/Colour: yellow-brown crystalline powder
• Vapor Pressure: 7.01E-08mmHg at 25°C
• Melting Point: 259 °C (dec.)(lit.)
• Boiling Point: 422.2 °C at 760 mmHg
• PKA: 4.27±0.30(Predicted)
• Flash Point: 209.1 °C
• PSA: 53.09000
• Density: 1.51 g/cm³
• LogP: 2.00520
• Storage Temp.: 0-6°C
• Water Solubility.: Insoluble
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 179.03825660
• Heavy Atom Count: 13
• Complexity: 222

Purity/Quality:

99% ^*data from raw suppliers

5-Fluoroindole-2-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi; F
• Hazard Codes: Xi,F
• Statements: 36/37/38-15-10
• Safety Statements: 26-37/39-43-36-7/8

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1F)C=C(N2)C(=O)O
• Uses: 5-Fluoroindole-2-carboxylic acid,is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff. Reactant for the synthesis of:Fungicidal agentsAntitumor agents2,3-dioxygenase (IDO) inhibitorsFactor Xa inhibitorsEnantioselective D3 receptor antagonistsLigands for hFPRL1 (or ALXR) receptor in inflammationAntibacterial agentsInhibitors of hepatitis C virus NS3·4A protease

Technology Process of 5-Fluoroindole-2-carboxylic acid

There total 8 articles about 5-Fluoroindole-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: 95.0%

ethyl 5-fluoro-1H-indole-2-carboxylate (348-36-7) → 5-fluoroindole-2-carboxylic acid (399-76-8)

Guidance literature:

ethyl 5-fluoro-1H-indole-2-carboxylate; With sodium hydroxide; In methanol; water; for 1h; Reflux; Green chemistry;

With hydrogenchloride; In methanol; water; at 50 ℃; pH=3 - 4; Green chemistry;

Reference yield:

→ 5-fluoroindole-2-carboxylic acid (399-76-8)

Guidance literature:

With sodium hydroxide; sodium dithionite;

DOI:10.1021/ja01510a021

Reference yield:

(5-fluoro-2-nitro-phenyl)-pyruvic acid (782-10-5) → 5-fluoroindole-2-carboxylic acid (399-76-8)

Guidance literature:

With ammonium hydroxide; iron(II) sulfate;

upstream raw materials:

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

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

ethyl 2-[2-(4-fluorophenyl)hydrazinylidene]propanoate

4-fluorophenyldiazonium chloride

Downstream raw materials:

N-[Nα-(5-Fluoroindole-2-carbonyl)-Nδ-trityl-L-glutaminyl]-3-hydroxy-4-methoxyaniline

5-Fluoro-1H-indole-2-carboxylic acid [(1S)-benzyl-2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-amide

5-Fluoro-1H-indole-2-carboxylic acid [(1S)-(4-fluoro-benzyl)-2-morpholin-4-yl-2-oxo-ethyl]-amide

5-Fluoro-1H-indole-2-carboxylic acid [(1S)-(4-fluoro-benzyl)-2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-amide

Refernces

• 1、 Iioka, Ryoya,Yorozu, Kohei,Sakai, Yoko,Kawai, Rika,Hatae, Noriyuki,Takashima, Katsuki,Tanabe, Genzoh,Wasada, Hiroaki,Yoshimatsu, Mitsuhiro. "Synthesis of Azepino[1,2-a]indole-10-amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent". supporting information. p. 1553 - 1558. Retrieved 2021/02/26.
• 2、 -. "Substituted indole - 2 - formic acid (by machine translation)". Paragraph 0040; 0043. . Retrieved 2017/10/28.