399-76-8

Basic information

• Product Name: 5-Fluoroindole-2-carboxylic acid
• Synonyms: TIMTEC-BB SBB010058;AKOS JY2082860;5-FLUORO-1H-INDOLE-2-CARBOXYLIC ACID;5-FLUOROINDOLE-2-CARBOXYLIC ACID;2-CARBOXY-5-FLUOROINDOLE;5-Fluoroindole-2-carboxylicacid,99%;5-Fluoroindole-2-carboxylic acid 99%;5-Fluoro-2-indolecarboxylic acid
• CAS NO: 399-76-8
• Molecular Formula: C₉H₆FNO₂
• Molecular Weight: 179.15
• EINECS: 206-919-5
• Product Categories: Indole/indoline/oxindole;Indole and Indoline;Indoles and derivatives;Indoles;Indole;Building Blocks;Heterocyclic Building Blocks
• Mol File: 399-76-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 259 °C (dec.)(lit.)
• Boiling Point: 422.2 °C at 760 mmHg
• Flash Point: 209.1 °C
• Appearance: Yellow-brown/Crystalline Powder
• Density: 1.3231 (estimate)
• Vapor Pressure: 7.01E-08mmHg at 25°C
• Storage Temp.: 0-6°C
• PKA: 4.27±0.30(Predicted)
• Water Solubility: Insoluble
• BRN: 153217
• CAS DataBase Reference: 5-Fluoroindole-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Fluoroindole-2-carboxylic acid(399-76-8)
• EPA Substance Registry System: 5-Fluoroindole-2-carboxylic acid(399-76-8)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/37/38-15-10
• Safety Statements: 26-37/39-43-36-7/8
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 399-76-8(Hazardous Substances Data)

Usage

Chemical Properties

yellow-brown crystalline powder

Uses

Different sources of media describe the Uses of 399-76-8 differently. You can refer to the following data:
1. 5-Fluoroindole-2-carboxylic acid,is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.
2. 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

General Description

5-Fluoroindole-2-carboxylic acid is an antagonist of the glycine site within the NMDA (N-methyl-D-aspartate) receptor complex.

InChI:InChI=1/C9H6FNO2/c10-6-1-2-7-5(3-6)4-8(11-7)9(12)13/h1-4,11H,(H,12,13)/p-1

Upstream product

• 351-64-4 ethyl 2-[2-(4-fluorophenyl)hydrazinylidene]propanoate 
• 371-40-4 4-fluoroaniline 
• 823-85-8 4-fluorophenyhydrazine hydrochloride 
• 20893-71-4 4-fluorophenyldiazonium chloride 
• 782-10-5 (5-fluoro-2-nitro-phenyl)-pyruvic acid 
• 348-36-7 ethyl 5-fluoro-1H-indole-2-carboxylate 

Downstream Products

• 399-52-0 5-fluoro-1H-indole 
• 186392-11-0 (2R,3S)-3-[(5-Fluoro-1H-indole-2-carbonyl)-amino]-2-hydroxy-4-phenyl-butyric acid methyl ester 
• 79112-09-7 5-fluoroindole-2-carboxylic acid chloride 
• 220941-93-5 5-fluoro-2-{[4-(2-pyridinyl)-1-piperazinyl]methyl}-1H-indole 
• 1228694-08-3 methyl (S)-5-(benzyloxy)-1-(chloromethyl)-3-(5-fluoroindole-2-carbonyl)-1,2-dihydropyrrolo[3,2-e]indole-2-carboxylate 
• 99532-53-3 1-(5-fluoro-1H-indol-3-yl)ethan-1-one 
• 1186643-15-1 N-((1S)-1-{[(1S,4S)-5-({[(2,5-dichlorophenyl)sulfonyl]amino}acetyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]carbonyl}-2,2-dimethylpropyl)-5-fluoro-1H-indole-2-carboxamide 
• 1609461-68-8 tert-butyl 2-amino-4-(4-(5-fluoro-1H-indole-2-carboxamido)phenyl)-1H-imidazole-1-carboxylate 

Relevant articles and documents

[18F]-labeled positron emission tomography ligand for the histamine H4 receptor

We synthesized 5-[18F]-fluoro-1H-indol-2-yl)(4-methyl-1-piperazinyl)methanone ([18F]5) via a Suzuki approach starting from a protected pinacol borane precursor followed by acidic hydrolysis of the t-Boc protecting group. The non-optimized radiochemical yield was 5.7 ± 1.35%, radiochemical purity was over 99%, and molar activity was 100.7 ± 34.5 GBq/μmol (n = 3). [18F]5 was stable in rat plasma for at least 4 h and was evaluated by μPET imaging and biodistribution using a unilateral quinolinic acid rat model of neuroinflammation. The time-activity curve showed that [18F]5 entered the brain immediately after intravenous injection and then left it progressively with a very low level reached from 30 min after injection. The biodistribution study showed no difference in the accumulation of [18F]5 between the lesioned and intact side of the brain and between control rats and animals pretreated with a saturating dose of JNJ-7777120 as a specific H4R antagonist. Hence, despite its in vitro nanomolar affinity for H4R, and its ability to cross the blood–brain barrier in rats, [18F]5 does not appear suitable to image in vivo the receptor by PET.

Facile synthesis of indolelactones using Mn(III)-based oxidative substitution-cyclization reaction

Based on the oxidation of indole with Mn(OAc)3 in the presence of 1,1-diarylethenes affording 3-vinyl-substituted indoles, a similar oxidation using indole-2-carboxylic acids was evaluated in order to effectively introduce the substituent group to the C-3 position of the indolecarboxylic acids. The coupling reaction followed by oxidative cyclization smoothly proceeded at room temperature in an AcOH-HCO2H mixed solvent to give the desired indolelactones in high yields. The reaction details, the structure determination of the products and a brief reaction mechanism are described.

Synthesis of 3,3-Dihalo-2-oxindoles from 2-Substituted Indoles via Halogenation–Decarboxylation/Desulfonamidation–Oxidation Process

A novel one-pot reaction which combines halogenation, decarboxylation/desulfonamidation with oxidation has been developed. Diverse valuable 3,3-dihalo-2-oxindole compounds can be produced rapidly and safely with isolated yields of up to 98% under mild conditions. (Figure presented.).