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

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

Uses

Used in Organic Synthesis:
5-Fluoroindole-2-carboxylic acid is used as a key intermediate for the development of novel organic compounds, contributing to the advancement of chemical research and innovation.
Used in Pharmaceuticals:
5-Fluoroindole-2-carboxylic acid is used as a reactant for the synthesis of various pharmaceutical agents, such as:
Antitumor agents: It plays a role in the development of cancer-fighting drugs.
2,3-dioxygenase (IDO) inhibitors: These inhibitors are used to modulate immune responses and have potential applications in cancer treatment.
Factor Xa inhibitors: These inhibitors are crucial in the development of anticoagulant medications.
Enantioselective D3 receptor antagonists: These antagonists are used in the treatment of various central nervous system disorders.
Ligands for hFPRL1 (or ALXR) receptor in inflammation: They are involved in the regulation of inflammatory responses.
Antibacterial agents: They are used in the development of new antibiotics to combat bacterial infections.
Inhibitors of hepatitis C virus NS3·4A protease: These inhibitors are essential in the treatment of hepatitis C.
Used in Agrochemicals:
5-Fluoroindole-2-carboxylic acid is used as a reactant in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural products to enhance crop protection and yield.
Used in Dyestuff:
5-Fluoroindole-2-carboxylic acid is used as an intermediate in the production of dyes and pigments, playing a vital role in the textile and coloring industries.

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

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

Downstream Products

• 399-52-0 5-fluoro-1H-indole 
• 136816-84-7 1-<(5-fluoroindol-2-yl)carbonyl>-4-<3-<(methylethyl)amino>-2-pyridyl>piperazine 
• 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 
• 518058-89-4 C₁₆H₁₃FN₂O₂ 
• 518059-66-0 C₁₅H₁₁FN₂O₂ 
• 518058-82-7 C₁₆H₁₂F₂N₂O 
• 945255-49-2 C₄₁H₅₉FN₆O₆ 
• 462068-77-5 5-fluoro-1H-indole-2-carboxamide 
• 220941-93-5 5-fluoro-2-{[4-(2-pyridinyl)-1-piperazinyl]methyl}-1H-indole 
• 343-90-8 3-dimethylaminomethyl-5-fluoroindole 
• 443-73-2 (5-fluoroindol-3-yl)acetic acid 

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.

Synthesis of Azepino[1,2-a]indole-10-amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent

Lewis acid-catalyzed [6+1] annulation reactions of 2-cyano-1-propargyl- and 2-alkynyl-1-cyanomethyl-indoles with Reformatsky reagent are described. 8-Aryl, 8-alkyl-, 8-hetaryl-, 9-aryl, and 9-alkyl-azepino[1,2-a]indole amines were obtained through a 7-endo-mode cyclization of the β-aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2-a]indoles analogs against the HCT-116 cells were also examined.

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.

Substituted indole - 2 - formic acid (by machine translation)

This invention relates to a substituted indole - 2 - carboxylic acid synthesis method, is to replace the phenyl hydrazine hydrochloride or arylhydrazines as raw materials, through with pyruvic acid ethyl ester cheng zong, Fischer indole synthesis by reaction of substituted indole - 2 - carboxylic acid ethyl ester, hydrolysis to obtain the substituted - 2 - carboxylic acid. Product purity is greater than 97%, the reaction yield is 64%. Synthesis method of the invention with non-harsh conditions, the operation is simple, and environmental friendliness, it has certain economic benefits. It is a kind of raw materials are easy, simple operation, three wastes, high yield of indole - 2 - carboxylic acid synthesis method. (by machine translation)

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.).

Synthesis and anti-tumor activity of 2-amino-3-cyano-6-(1H-indol-3-yl)-4- phenylpyridine derivatives in vitro

A series of novel 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives were synthesized and their cytotoxic activity against A549, H460, HT-29 and SMMC-7721 cell lines was evaluated in vitro. Among them, ten compounds (10, 11, 14, 16, 17, 26, 27, 29, 30 and 31) displayed excellent anti-tumor activity against different cell lines. The most promising compound 27 showed strong anti-tumor activity against A549, H460, HT-29 and SMMC-7721 cell lines with IC50 values of 22, 0.23, 0.65 and 0.77 nM, which were 2.6-, 83-, 1.1 × 103- and 2.0 × 103- fold more active than MX-58151 (IC50 values of 0.058, 0.019, 0.70 and 1.53 μM), respectively.