313337-34-7

Basic information

• Product Name: 4-fluoro-1H-indole-7-carboxylic acid
• Synonyms: 4-fluoro-1H-indole-7-carboxylic acid;4-FLUORO-7-INDOLE CARBOXYLIC ACID;7-Carboxy-4-fluoro-1H-indole;1H-Indole-7-carboxylic acid, 4-fluoro-;4-Fluoro indole-7-carboxylic aicd
• CAS NO: 313337-34-7
• Molecular Formula: C₉H₆FNO₂
• Molecular Weight: 179.149
• Mol File: 313337-34-7.mol

Chemical Properties

• Boiling Point: 421.442°C at 760 mmHg
• Flash Point: 208.681°C
• Appearance: /
• Density: 1.51g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.692
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-fluoro-1H-indole-7-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-fluoro-1H-indole-7-carboxylic acid(313337-34-7)
• EPA Substance Registry System: 4-fluoro-1H-indole-7-carboxylic acid(313337-34-7)

Safety Data

• Hazardous Substances Data: 313337-34-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluoro-1H-indole-7-carboxylic acid is used as a key intermediate for the synthesis of potential drug candidates due to its unique chemical properties. Its structure and reactivity allow for the development of various pharmaceuticals with potential therapeutic applications.
Used in Agrochemical Production:
4-Fluoro-1H-indole-7-carboxylic acid is also utilized as an intermediate in the production of various agrochemicals. Its chemical properties contribute to the creation of compounds with potential applications in agriculture, such as pesticides or plant growth regulators.
Used in Organic Synthesis:
As a versatile building block, 4-fluoro-1H-indole-7-carboxylic acid is employed in organic synthesis for the preparation of diverse compounds with potential biological activity. Its unique structure and reactivity enable the synthesis of new molecules with potential applications in various fields, including medicine, materials science, and environmental science.

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

Upstream product

• 124-38-9 carbon dioxide 
• 292636-09-0 7-bromo-4-fluoro-1H-indole 
• 446-09-3 2-bromo-5-fluoronitrobenzene 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 313337-33-6 4-fluoro-1H-indole-7-carbonitrile 

Downstream Products

• 313337-35-8 methyl 4-fluoro-1H-indole-7-carboxylate 
• 389629-09-8 3-[2-(4-benzoyl-piperazin-1-yl)-2-oxo-acetyl]-4-fluoro-1H-indole-7-carboxylic acid methylamide 
• 389628-30-2 C₂₃H₂₀FN₃O₅ 
• 389628-31-3 C₂₂H₁₈FN₃O₅ 
• 389628-29-9 3-oxoacetyl chloride of 4-fluoro-7-carbomethoxy indole 
• 13754-38-6 N-Benzoylpiperazine 

Relevant articles and documents

Inhibitors of HIV-1 attachment. Part 7: Indole-7-carboxamides as potent and orally bioavailable antiviral agents

A series of substituted carboxamides at the indole C7 position of the previously described 4-fluoro-substituted indole HIV-1 attachment inhibitor 1 was synthesized and the SAR delineated. Heteroaryl carboxamide inhibitors that exhibited pM potency in the primary cell-based assay against a pseudotype virus expressing a JRFL envelope were identified. The simple methyl amide analog 4 displayed a promising in vitro profile, with its favorable HLM stability and membrane permeability translating into favorable pharmacokinetic properties in preclinical species.

In search of simplicity and flexibility: A rational access to twelve fluoroindolecarboxylic acids

All twelve indolecarboxylic acids 1-12 carrying both a fluorine substituent and a carboxy group at the benzo ring have been prepared either directly from the corresponding fluoroindoles 13-16 or from the chlorinated derivatives 22, 23 and 25 by hydrogen/metal permutation ("metalation"), or from the bromo- or iodofluoroindoles 17-20 and 26, 27, 29 and 30 by halogen/metal permutation, the organometallic intermediate being each time trapped with carbon dioxide. In most, though not all cases, the nitrogen atom in the five-membered ring had to be protected by a trialkylsilyl group. Some of the bromo- or iodofluoroindoles (26 and 27) were successfully subjected to a basicity gradient-driven selective migration of the heavy halogen. An unexpected finding on the way to the target compounds were the rigorously site-selective metalation of the 5-fluoro-N-(trialkylsilyl)indole (14b; exclusive deprotonation of the 4-position). The fluoroindoles 13-16, although previously known, were accessed more conveniently from suitably substituted nitrobenzenes using the Bartoli or the Leimgruber-Batcho method. A new and very attractive indole synthesis was elaborated consisting of the ortho-lithiation of an N-acyl-protected aniline followed by ortho-formylation, Wittig chloromethylenation and base-catalyzed cyclization accompanied by dehydrochlorination. These five consecutive steps can be contracted to a convenient one-pot protocol. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Indole, indazole and indoline derivatives as CETP inhibitors

The present invention relates to compounds of formula (I): wherein —X—Y—, R1 to R11 and n are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prevention of diseases which are mediated by CETP inhibitors.

Indole, azaindole and related heterocyclic sulfonylureido piperazine derivatives

This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with sulfonylureido piperazine derivatives of Formula I. These compounds possess unique antiviral activity, whether used alone or in combination with other antivirals, antiinfectives, immunomodulators or HIV entry inhibitors. More particularly, the present invention relates to the treatment of HIV and AIDS. 1wherein: Z is 2Q is selected from the group consisting of: 3—W— is 4—represents a carbon-carbon bond or does not exist; and A is NR13R14.

INDOLE, AZAINDOLE AND RELATED HETEROCYCLIC UREIDO AND THIOUREIDO PIPERAZINE DERIVATIVES

This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with ureido and thioureido piperazine derivatives of Formula (I). These compounds possess unique antiviral activity, whether used alone or in combination with other antivirals, antiinfectives, immunomodulators or HIV entry inhibitors. More particularly, the present invention relates to the treatment of HIV and AIDS. The compounds of Formula (I) are Formula (I) wherein:Y is O or S;Z is Formula (II); Q is selected from the group consisting of Formula (A) and Formula (B); m is 2;A is NRR; and-W- is Formula (C).

Antiviral indoleoxoacetyl piperazine derivatives

This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with indoleoxoacetyl piperazine derivatives. These compounds possess unique antiviral activity, whether used alone or in combination with other antivirals, antiinfectives, immunomodulators or HIV entry inhibitors. More particularly, the present invention relates to the treatment of HIV and AIDS.