41201-58-5

Basic information

• Product Name: 5-Fluoro-2-methylindan-1-one
• Synonyms: 2-METHYL-5-FLUOROINDANONE;5-Fluoro-2-methylindan-1-one;5-FLUORO-2-METHYLIDANONE;5-fluoro-2-Methyl-2,3-dihydro-1H-inden-1-one;5-Fluoro-2-Methylindanone
• CAS NO: 41201-58-5
• Molecular Formula: C₁₀H₉FO
• Molecular Weight: 164.18
• EINECS: 255-261-5
• Mol File: 41201-58-5.mol

Chemical Properties

• Boiling Point: 251.817 °C at 760 mmHg
• Flash Point: 97.959 °C
• Appearance: /
• Density: 1.179 g/cm³
• Vapor Pressure: 0.02mmHg at 25°C
• Refractive Index: 1.533-1.5339
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-Fluoro-2-methylindan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Fluoro-2-methylindan-1-one(41201-58-5)
• EPA Substance Registry System: 5-Fluoro-2-methylindan-1-one(41201-58-5)

Safety Data

• Hazardous Substances Data: 41201-58-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
5-Fluoro-2-methylindan-1-one is used as a key intermediate in the synthesis of pharmaceutical compounds for various therapeutic applications. Its unique structure allows for the development of new drugs with potential novel mechanisms of action and improved pharmacological properties.
Used in Drug Design:
5-Fluoro-2-methylindan-1-one is employed as a structural component in drug design, where its fluorine and methyl substituents can influence the compound's lipophilicity, metabolic stability, and binding affinity to target proteins. This can lead to the creation of more effective and selective drugs with fewer side effects.
Used in Chemical Synthesis:
5-Fluoro-2-methylindan-1-one serves as a versatile building block in the synthesis of other chemical compounds, including complex organic molecules and specialty chemicals. Its reactivity and functional group compatibility make it a valuable precursor in organic synthesis processes.
Used in Academic Research:
5-Fluoro-2-methylindan-1-one is utilized in academic research settings to study the effects of structural modifications on the properties and biological activities of indanone derivatives. This can provide valuable insights into the structure-activity relationships of these compounds and guide the design of more potent and selective drug candidates.
Used in Industrial Chemical Production:
5-Fluoro-2-methylindan-1-one may find applications in the industrial production of specialty chemicals, such as agrochemicals, dyes, and other fine chemicals. Its unique structural features can contribute to the development of novel products with improved performance characteristics.

InChI:InChI=1/C10H9FO/c1-6-4-7-5-8(11)2-3-9(7)10(6)12/h2-3,5-6H,4H2,1H3

Upstream product

• 462-06-6 fluorobenzene 
• 20769-85-1 2-bromoisobutyric acid bromide 
• 337913-25-4 phosphorus pentaoxide 
• 700-84-5 5-fluoro-1-indanone 
• 74-88-4 methyl iodide 
• 653-92-9 methyl 2-bromo-4-fluorobenzoate 
• 41201-57-4 α-methyl-3-fluorohydrocinnamic acid 
• 58472-45-0 1-(p-fluorophenyl)-2-methyl-2-propen-1-one 
• 58472-46-1 4'-fluoro-2-methyl-3-chloro-propiophenone 
• 53012-99-0 3-dimethylamino-4'-fluoro-2-methylpropiophenone 
• 459-57-4 4-fluorobenzaldehyde 
• 22138-73-4 3-(4-fluorophenyl)-2-methylpropanoic acid 
• 22138-72-3 (E)-3-(4-fluorophenyl)-2-methylacrylic acid 
• 456-48-4 3-Fluorobenzaldehyde 

Downstream Products

• 32004-66-3 5-fluoro-2-methyl-1H-indene-3-acetic acid 

Relevant articles and documents

Synthesis of rigid trichostatin A analogs as HDAC inhibitors

New inhibitors of histone deacetylase (HDAC) have been synthesized and evaluated for their activity toward non small lung cancer cell line H661. Their design is based on indanone (or tetralone) systems leading to trichostatin A (TSA) analogs with limited conformational mobility. Molecular modelization at the AM1 level revealed that the conformations of indane-based analogs and TSA bound to HDAC like protein are similar. The synthesis of these new analogs was achieved by alkylation of an appropriate indanone (or tetralone) to introduce the side chain bearing a terminal ester group, the latter being a precursor of hydroxamic acid and aminobenzamide derivatives. Hydroxamic acids with the TSA side chain were found to be the most active compounds and the presence of the dimethylamino group on the phenyl ring turned out to be essential to achieve low micromolar activities against H661 cancer cells.

Nickel-Catalyzed Domino Heck-Type Reactions Using Methyl Esters as Cross-Coupling Electrophiles

While esters are frequently used as traditional electrophiles in substitution chemistry, their application in cross-coupling chemistry is still in its infancy. This work demonstrates that methyl esters can be used as coupling electrophiles in Ni-catalyzed Heck-type reactions through the challenging cleavage of the C(acyl)?O bond under relatively mild reaction conditions at either 80 or 100 °C. With the σ-NiII intermediate generated from the insertion of acyl NiII species into the tethered C=C bond, carbonyl-retentive products were formed by domino Heck/Suzuki–Miyaura coupling and Heck/reduction pathways when organoboron and mild hydride nucleophiles are used.

Extending the Substrate Scope in the Hydrogenation of Unfunctionalized Tetrasubstituted Olefins with Ir-P Stereogenic Aminophosphine-Oxazoline Catalysts

Air-stable and readily available Ir-catalyst precursors modified with MaxPHOX-type ligands have been successfully applied in the challenging asymmetric hydrogenation of tetrasubstituted olefins under mild reaction conditions. Gratifyingly, these catalyst precursors are able to efficiently hydrogenate not only a range of indene derivatives (ee's up to 96%) but also 1,2-dihydronapthalene derivatives and acyclic olefins (ee's up to 99%), which both constitute the most challenging substrates for this transformation.

Synthesizing method of indanone compound

The invention discloses a synthesizing method of an indanone compound. The synthesizing method comprises the following steps of respectively adding a catalyst and an antioxidant into a reaction bottle, then adding a compound shown in a formula (2), adding a solvent, and reacting for 2 to 6h at the temperature of 70 to 120 DEG C under the argon protection atmosphere, so as to obtain the indanone compound, wherein the catalyst is selected from any one of Cu(OAc)2, CuCl2 (copper (II) chloride), CuBr2 (copper (II) bromide), CuO (copper oxide), CuF2 (copper fluoride), Cu(OTf) 2, Cu(OH)2 (copper hydroxide), Cu(NO3)2 (copper nitrate), CuCl (copper chloride), CuBr (copper bromide), CuI (cuprous iodide) and Cu2O (cuprous oxide); the oxidant is tert-butyl hydroperoxide; the solvent is toluene. The synthesizing method has the advantages that a novel concept of the indanone compound is provided; the copper catalyst is used, the price of copper is low, the reserve amount is rich, the environment-friendly effect is realized, and the hydroacylation reaction catalyzed by copper meets the requirements of green chemistry.

COMPOUNDS, COMPOSITIONS AND METHODS OF TREATING CANCER

Disclosed are compounds of formulas I and II, in which R, R0, R1-R4, R7-R10, n, X, Y, Y', and E are as described herein, pharmaceutical compositions containing such compounds. The compounds and pharmaceutical compositions are for use in treating or preventing diseases, for example, cancer.

INDENYL COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND MEDICAL USES THEREOF

Disclosed are compounds, for example, compounds of formula I, wherein R, R0, R1-R8, n, X, Y, Y′, and E are as described herein, pharmaceutical compositions containing such compounds, and methods of treating or preventing a disease or condition, for example, cancer.

METHOD OF TREATING OR PREVENTING RAS-MEDIATED DISEASES

Disclosed are compounds, for example, a compound of formula I, wherein R, R0, R1-R8, n, X, Y, Y′, and E are as described herein, pharmaceutical compositions containing such compounds, and methods of treating or preventing a disease or condition for example, cancer, mediated by the ras gene.

Chemical compounds and processes

Haloalkyl derivatives of aromatic compounds are prepared via reaction with dialkoxy or aralkoxy alkanes in the presence of a Lewis acid.

Indenylidene-3-acetic acid process for preparing indene acetic acids

Process for preparing 5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-indene-3-acetic acid by reacting fluorobenzene with an acid halide, to form an indanone, reaction of the indanone with a methylthio (or methylsulfinyl)benzyl compound to form 5-fluoro-2-methyl-1-(p-methylthiobenzyl) or (p-methylsulfinylbenzyl)-indene and reacting said indene with a glyoxylic acid. The invention also relates to intermediates thereof and processes for said intermediates.