399-72-4

Basic information

• Product Name: 5-Fluoro-2-methylindole
• Synonyms: 5-FLUORO-2-METHYL-1H-INDOLE;5-FLUORO-2-METHYLINDOLE;1H-Indole, 5-fluoro-2-methyl-
• CAS NO: 399-72-4
• Molecular Formula: C₉H₈FN
• Molecular Weight: 149.16
• EINECS: 1592732-453-0
• Product Categories: Heterocycles series;Pyrroles & Indoles;Indole;Pyrroles & Indoles;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 399-72-4.mol

Chemical Properties

• Melting Point: 98-101 °C(lit.)
• Boiling Point: 112-120C
• Flash Point: 116.6 °C
• Appearance: /Solid
• Density: 1.219 g/cm₃
• Vapor Pressure: 0.0121mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 16.73±0.30(Predicted)
• CAS DataBase Reference: 5-Fluoro-2-methylindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Fluoro-2-methylindole(399-72-4)
• EPA Substance Registry System: 5-Fluoro-2-methylindole(399-72-4)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-25
• Safety Statements: 26-36-45-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 399-72-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Fluoro-2-methylindole is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to serve as a building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 5-Fluoro-2-methylindole is utilized as a research tool to study the properties and reactivity of indole derivatives. Its distinct chemical structure makes it a valuable compound for understanding the behavior of similar molecules and for developing new synthetic methods.
Used in Material Science:
5-Fluoro-2-methylindole can be employed in the development of novel materials with specific properties. Its unique structure and functional groups can be exploited to create materials with tailored characteristics for various applications, such as in electronics, optics, or sensors.
Used in Agrochemical Industry:
In the agrochemical industry, 5-Fluoro-2-methylindole may be used as a starting material for the synthesis of bioactive compounds with potential applications in pest control, crop protection, or as additives in the agricultural sector.
Used in Dye and Pigment Industry:
Due to its chemical structure, 5-Fluoro-2-methylindole can be used as a precursor in the synthesis of dyes and pigments with specific color properties. These dyes and pigments can be utilized in various industries, such as textiles, plastics, and printing.

InChI:InChI=1/C9H8FN/c1-6-4-7-5-8(10)2-3-9(7)11-6/h2-5,11H,1H3

Upstream product

• 557-93-7 2-bromoprop-1-ene 
• 1003-98-1 2-bromo-4-fluoroaniline 
• 1082469-90-6 (Z)-3-(4-fluorophenylamino)-but-2-enoic acid methylester 
• 1259438-23-7 tert-butyl (Z)-3-(4-fluorophenylamino)-but-2-carboxylate 
• 1259438-24-8 benzyl (Z)-3-(4-fluorophenylamino)-but-2-carboxylate 
• 98621-77-3 5-fluoro-2-methyl-1H-indole-3-carboxylic acid 
• 1313753-25-1 tert-butyl 5-fluoro-2-methyl-1H-indole-3-carboxylate 
• 823-85-8 4-fluorophenyhydrazine hydrochloride 
• 67-64-1 acetone 
• 700-36-7 2-bromo-4-fluoronitrobenzene 
• 1266659-06-6 1-(5-fluoro-2-nitrophenyl)propan-2-one 
• 399-52-0 5-fluoro-1H-indole 
• 74-88-4 methyl iodide 
• 267002-55-1 2-allyl-4-fluorophenylamine 

Downstream Products

• 479421-98-2 methyl 4-[[2-(5-fluoro-2-methyl-1H-indol-3-yl)ethyl]sulfonyl]benzoate 
• 815586-68-6 5-fluoro-2-methyl-1H-indole-3-carboxaldehyde 

Relevant articles and documents

Cobalt-Catalyzed Dearomatization of Indoles via Transfer Hydrogenation to Afford Polycyclic Indolines

A cobalt-catalyzed dearomatization of indoles via transfer hydrogenation with HBpin and H2O has been developed. This reaction offered a straightforward platform to access hexahydropyrido[1,2-a]indoles in high regio- and chemoselectivity. A preliminary reaction mechanism was proposed on the basis of deuterium-labeling experiments, and a cobalt hydride species was involved in the reaction.

Method for preparing indole and derivatives thereof

The invention discloses a method for preparing indole and derivatives of indole. The method for preparing indole and the derivatives of indole is characterized by comprising the following two steps that (1) a catalyst, a ligand and alkali are added in a reaction tube, under the protection of nitrogen, beta-hydroxy ketone or ester is reacted with a mixed solution of o-nitro aryl halides for 3 to 8h in an oil bath pan at the temperature of 90 to 120 DEG C, and then cooled to room temperature after reaction, and extracted, washed, dried and subjected to chromatography to obtain a product of o-nitro alpha-aryl ketone or ester; (2) o-nitro alpha-aryl ketone or ester obtained in the step (1), a reducing agent system and a solvent are added to the reaction tube, and reacted for 3 to 8h at the temperature of 60 to 100 DEG C, and then extracted, washed, dried and subjected to chromatography after being reacted to obtain a target product of indole and the derivatives of indole. Reaction raw materials, the catalyst, the ligand, the alkali and the solvent used in the invention are all industrial commodities, and simple and readily available, wide in sources, cheap in price, and further very stable in performances, and with no need for special storage conditions; in addition, the method for preparing indole and the derivatives of indole disclosed by the invention has the characteristics of low cost, high yield, simple process, less pollution and the like.

Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones by general Pd-catalyzed retro-aldol/α-arylation

Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones is described in this report by using a general Pd-catalyzed tandem reaction of β-hydroxy carbonyl compounds with aryl halides bearing an ortho-nitro, -ester or -cyano substituent. A key retro-aldol/α-arylation reaction is involved that merges classic Pd cross-coupling chemistry with novel Pd-promoted retro-aldol C-C activation to produce α-arylated ketones or esters. Subsequent intramolecular condensation of the carbonyl with the ortho-synthon gives target heterocycles. The use of common, commercially available and cheap substrates and catalyst system adds additional synthetic advantages to the conceptual significance.

Palladium-catalysed direct C-2 methylation of indoles

A direct C-2 methylation reaction of indoles bearing a readily removable N-2-pyrimidyl moiety as a site-specific directing group has been developed with a palladium catalyst. This reaction relied on the use of KF to promote efficient methylation. A moderate to good yield was achieved in a range of indole substrates.

Palladium-catalyzed diastereoselective oxyarylation of 2-alkylindoles

Diastereoselective oxyarylation of N-protected 2-alkylindoles with commercially available boronic acids and TEMPO as a mild oxidant to give N-protected 2-aryl-2-alkyl-3-(2-chloroacetoxy)indolines is described. Reactions are easy to conduct, and product indolines containing a fully substituted C-center are obtained in good yields with good to excellent selectivities.

A N-heterocyclic carbene (NHC) platinum complex as pre-catalyst for the intramolecular hydroamination of olefins with secondary alkylamines and oxidative amination of ω-alkenic amines

A N-heterocyclic carbene (NHC) platinum complex 3 prepared from BINAM was found to be a highly effective pre-catalyst for the intramolecular hydroamination of olefins with secondary alkylamines to give the corresponding intramolecular hydroamination products in excellent yields. The substrate scope has been carefully examined and the plausible reaction mechanism has been also proposed.

Exploring the oxidative cyclization of substituted N-aryl enamines: Pd-catalyzed formation of indoles from anilines

The direct Pd-catalyzed oxidative coupling of two C-H-bonds within N-aryl-enamines 1 allows the efficient formation of differently substituted indoles 2. In this cross-dehydrogenative coupling, many different functional groups are tolerated and the starting material N-aryl-enamines 1 can be easily prepared in one step from commercially available anilines. In addition, the whole sequence can also be run in a one-pot fashion. Optimization data, mechanistic insight, substrate scope, and applications are reported in this full paper. Copyright

Pd PEPPSI-IPr-mediated reactions in metal-coated capillaries under MACOS: The synthesis of indoles by sequential aryl amination/heck coupling

A method has been devised for the microwave-assisted, continuous-flow preparation of indole alkaloids by a two-step aryl amination/cross-coupling sequence of bromoalkenes and 2-bromoanilines. This process requires both the presence of a metal-lined flow tube (a 1180 micron capillary) and the Pd PEPPSI-IPr catalyst; without either, the catalyst or the film, there is zero turnover of this catalytic process. A silver film has been shown to provide some conversion (48-62%), but optimal results (quantitative) across a variety of bromoalkenes and bromoanilines were achieved by using a highly porous palladium film. Possible roles for the Pd film are considered, as is the interplay of the catalyst and the film.

Inhibition of cytosolic phospholipase A2α: Hit to lead optimization

Compound 1 was previously reported to be a potent inhibitor of cPLA 2α in both artificial monomeric substrate and cell-based assays. However, 1 was inactive in whole blood assays previously used to characterize cyclooxygenase and lipoxygenase inhibitors. The IC50 of 1 increased dramatically with cell number or lipid/detergent concentration. In an attempt to insert an electrophilic ketone between the indole and benzole acid moieties, we discovered that increasing the distance between the two moieties gave a compound with activity in the GLU (7-hydroxycoumarinyl-γ- linolenate) micelle assay, which contains lipid and detergent. Extensive structure-activity relationship work around this lead identified a potent pharmacophore for cPLA2α inhibition. The IC50s between the GLU micelle and rat whole blood assays correlated highly. No correlation was found for other parameters, including lipophilicity or acidity of the required acid functionality. Compounds 25, 39, and 94 emerged as potent, selective inhibitors of cPLA2α and represent well-validated starting points for further optimization.

2-Substituted-indole-1-lower-alkanecarboxamides

2-Substituted-indole-1-lower-alkanecarboxamides, prepared by amidation of the corresponding acid or ester; by hydrolysis or thiohydrolysis of the corresponding carbonitrile; by alkylation of a suitable indole with a halo-lower-alkanecarboxamide; or by hydrolysis of a 1-indolechlorosulfonylcarbamyl derivative, have anti-secretory and anti-ulcer activities.