348-26-5

Basic information

• Product Name: 5-FLUORO-1H-INDAZOLE
• Synonyms: 5-FLUORO-1H-INDAZOLE;5-Fluoroindazole;1H-Indazole, 5-fluoro-;5-fluoro-1H-indazole(SALTDATA: FREE)
• CAS NO: 348-26-5
• Molecular Formula: C₇H₅FN₂
• Molecular Weight: 136.13
• Product Categories: Indoles and derivatives;Halogenated Heterocycles;Heterocyclic Building Blocks;Indazoles;Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocyclic Fluorinated Building Blocks;Other Fluorinated Heterocycles;Others
• Mol File: 348-26-5.mol

Chemical Properties

• Melting Point: 119-125°C
• Boiling Point: 274.9 °C at 760 mmHg
• Flash Point: 120.1 °C
• Appearance: /
• Density: 1.37 g/cm³
• Vapor Pressure: 0.009mmHg at 25°C
• Refractive Index: 1.659
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.90±0.40(Predicted)
• CAS DataBase Reference: 5-FLUORO-1H-INDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-FLUORO-1H-INDAZOLE(348-26-5)
• EPA Substance Registry System: 5-FLUORO-1H-INDAZOLE(348-26-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 348-26-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
5-Fluoro-1H-indazole is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure and potential biological activities make it a valuable component in the development of new drugs.
Used in Drug Discovery:
In the field of drug discovery, 5-Fluoro-1H-indazole is employed as a lead compound for identifying potential therapeutic agents. Its chemical properties and interactions with biological targets can provide insights into the design of novel drugs with improved efficacy and safety profiles.
Used in Chemical Synthesis:
5-Fluoro-1H-indazole is used as a building block in the synthesis of more complex organic molecules. Its reactivity and structural features can be exploited to create a wide range of chemical products, including advanced materials and specialty chemicals.
Used in Academic Research:
In academic settings, 5-Fluoro-1H-indazole is utilized as a research tool to study various aspects of chemistry, such as reaction mechanisms, molecular interactions, and the properties of heterocyclic compounds. This knowledge can contribute to the advancement of the chemical sciences and the development of new technologies.
Used in Industrial Applications:
Although primarily a research chemical, 5-Fluoro-1H-indazole may also find applications in certain industrial processes, such as the production of specialty chemicals or the development of new materials with unique properties. Its versatility and potential for modification make it a candidate for various industrial applications.

InChI:InChI=1/C7H5FN2/c8-6-1-2-7-5(3-6)4-9-10-7/h1-4H,(H,9,10)

Upstream product

• 326-65-8 N-(4-fluoro-2-methylphenyl)acetamide 
• 452-71-1 4-fluor-2-methylaniline 
• 1979-36-8 2',5'-difluoroacetophenone 
• 141071-11-6 1-Acetyl-5-fluorindazol 
• 347-54-6 5-fluoro-2-hydroxybenzaldehyde 
• 94569-84-3 2-bromo-5-fluorobenzaldehyde 

Downstream Products

• 141071-11-6 1-Acetyl-5-fluorindazol 
• 858629-06-8 5-fluoro-3-iodo-1H-indazole 
• 78155-73-4 methyl 5-fluoro-1H-indazole-3-carboxylate 
• 1620816-72-9 5-fluoro-1-methyl-3,7-diphenyl-1H-indazole 
• 1210023-65-6 5-fluoro-1-methyl-1H-indazole 
• 885519-08-4 3-bromo-5-fluoro-1H-indazole 

Relevant articles and documents

A novel copper-catalyzed, hydrazine-free synthesis of N-1 unsubstituted 1H-indazoles using stable guanylhydrazone salts as substrates

A CuI-catalyzed, hydrazine-free transformation of 2-(2-bromoarylidene)guanylhydrazone hydrochlorides using Cs2CO3 as a base and DMEDA as a ligand at 120 °C for 5 h delivers substituted 1H-indazoles with yields up to 75%. The C,N double bond configuration of the substrates was determined by NMR experiments and quantum chemical calculations. The reaction mechanism was studied using quantum chemical calculations.

Visible-Light-Mediated N-Desulfonylation of N-Heterocycles Using a Heteroleptic Copper(I) Complex as a Photocatalyst

A photoredox protocol that uses a heteroleptic Cu (I) complex, [Cu(dq)(BINAP)]BF4, has been developed for the photodeprotection of benzenesulfonyl-protected N-heterocycles. A range of substrates was examined, including indazoles, indoles, pyrazoles, and benzimidazole, featuring both electron-rich and electron-deficient substituents, giving good yields of the N-heterocycle products with broad functional group tolerance. This transformation was also found to be amenable to flow reaction conditions.

Synthesis, antifungal activity and qsar of novel pyrazole amides as succinate dehydrogenase inhibitors

We design and synthesize a series of novel pyrazole amides based on the commercialized fungicides and our previous work. The antifungal activity was tested in vitro by mycelial growth inhibition assay. The results show that all the compounds are of antifungal activities against the tested fungi at different levels. Among them, N-(2-(7-bromo-5-chloro-1H-indazol-1-yl)phenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (Vk) exhibited higher antifungal activity than boscalid against two fungi. Molecular docking study revealed that the carbonyl oxygen atom of Vk forms two hydrogen bonds toward the hydroxyl hydrogens of TYR58 and TRP173.

Preparation method of indazole and application of indazole in medicine synthesis

The invention belongs to the field of chemicals, and relates to a preparation method of indazole and an application of the indazole in medicine synthesis. The invention discloses a preparation method of indazole and an application of the indazole in synthesizing 1H-indazole-3-carboxylic acid, lonidamine, a compound 8, a compound 9, a compound 10, axitinib, YD-3, YC-1 and similar substances thereof.

Copper(I) Oxide-Mediated Cyclization of o-Haloaryl N-Tosylhydrazones: Efficient Synthesis of Indazoles

An efficient synthesis of indazoles from readily accessible E/Z mixtures of o-haloaryl N-tosylhydrazones has been developed. The thermo-induced isomerization of N-tosylhydrazones is discussed. A series of valuable indazole derivatives are prepared in good yields, and the method has been successfully applied to the synthesis of the bioactive compounds, lonidamine, AF-2785, axitinib, YC-1 and YD-3.

SUBSTITUTED INDAZOLE COMPOUNDS AS IRAK4 INHIBITORS

The present invention provides substituted indazole compound of formula (I) and pharmaceutically acceptable salts thereof, and their use to inhibit IRAK4 and/or for the treatment of diseases or disorders induced by IRAK4.

A general synthesis of diversely substituted indazoles and hetero-aromatic derivatives from o-halo-(het)arylaldehydes or -phenones

A set of variously substituted indazoles and hetero-aromatic derivatives were synthesized from o-halo-(het)arylaldehydes using a palladium catalyzed amination followed by cyclization. Starting from phenones, this process was extended to give 3-substituted indazoles. Moreover, N-1-substituted-indazoles can be reached by this strategy using an optional selective N-1-alkylation step during the process. This methodology offers a general and easy route for the synthesis of regioselectively substituted indazoles.

Fluorinated analogues of marsanidine, a highly α2-AR/imidazoline I1 binding site-selective hypotensive agent. Synthesis and biological activities

The aim of these studies was to establish the influence of fluorination of the indazole ring on the pharmacological properties of two selective α2-adrenoceptor (α2-AR) agonists: 1-[(imidazolidin-2-yl)imino]-1H-indazole (marsanidine,

Synthesis and structure-activity relationships of a series of substituted 2-(1H-furo[2,3-g]indazol-1-yl)ethylamine derivatives as 5-HT2C receptor agonists

A series of novel indazole derivatives were synthesized, and their structure-activity relationships examined in order to identify potent and selective 5-HT2C receptor agonists. Among these compounds, (S)-2-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)-1-methylethylamine (YM348) had a good in vitro profile, that is, high agonistic activity to the human 5-HT2C receptor subtype (EC50 = 1.0 nM) and high selectivity over 5-HT2A receptors. This compound was also effective in a rat penile erection model when administered po.

4-Substituted indazoles as new inhibitors of neuronal nitric oxide synthase

A series of halo-1-H-indazoles has been synthesized and evaluated for its inhibitory activity on neuronal nitric oxide synthase. Introduction of bromine at the C4 position of the indazole ring system provided a compound almost as potent as the reference compound, that is, 7-nitroindazole (7-NI). The importance of position 4 is further demonstrated by the synthesis and pharmacological evaluation of the 4-nitroindazole which was also a potent inhibitor of NOS activity. These compounds also exhibited in vivo NOS inhibitory activity, as attested by potent antinociceptive effects following systemic administration.