174734-34-0

Basic information

• Product Name: 5-Methoxy-2-trifluoromethylindole
• Synonyms: 5-METHOXY-2-TRIFLUOROMETHYL INDOLE;5-Methoxy-2-(trifluoromethyl)-1H-indole;1H-Indole,5-methoxy-2-(trifluoromethyl)-
• CAS NO: 174734-34-0
• Molecular Formula: C10H8F3NO
• Molecular Weight: 215.17
• Product Categories: API intermediates
• Mol File: 174734-34-0.mol

Chemical Properties

• Melting Point: 50-51 °C
• Boiling Point: 301 °C
• Flash Point: 136 °C
• Appearance: /
• Density: 1.350
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-Methoxy-2-trifluoromethylindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methoxy-2-trifluoromethylindole(174734-34-0)
• EPA Substance Registry System: 5-Methoxy-2-trifluoromethylindole(174734-34-0)

Safety Data

• Hazardous Substances Data: 174734-34-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Methoxy-2-trifluoromethylindole is used as a key intermediate for the synthesis of various pharmaceuticals and agrochemicals. Its potent bioactive properties and unique chemical structure make it a valuable building block in the development of new drugs and research chemicals.
Used in Medicinal Chemistry:
5-Methoxy-2-trifluoromethylindole is used as a key intermediate in the development of new drug candidates. Its unique chemical structure and reactivity contribute to the discovery of novel compounds with potential therapeutic applications.
Used in Organic Synthesis:
5-Methoxy-2-trifluoromethylindole is used as a valuable tool in organic synthesis due to its unique chemical structure and reactivity. It can be employed in the synthesis of complex organic molecules and the development of new synthetic routes.
Used in Drug Discovery:
5-Methoxy-2-trifluoromethylindole is used in drug discovery processes to identify and develop new compounds with potential therapeutic effects. Its potent bioactive properties and unique chemical structure make it a promising candidate for the development of innovative drugs.
Used in Agrochemical Industry:
5-Methoxy-2-trifluoromethylindole is used as a building block in the synthesis of various agrochemicals. Its unique chemical structure and reactivity contribute to the development of new agrochemicals with improved efficacy and selectivity.

InChI:InChI=1/C10H8F3NO/c1-15-7-2-3-8-6(4-7)5-9(14-8)10(11,12)13/h2-5,14H,1H3

Upstream product

• 916974-26-0 N-[2-(bromomethyl)-4-methoxyphenyl]-2,2,2-trifluoroacetimidoyl chloride 
• 102-50-1 2-methyl-4-methoxyaniline 
• 104863-67-4 N-methoxy-N-methyltrifluoroacetamide 
• 129822-42-0 N-(tert-butoxycarbonyl)-4-methoxy-2-methylaniline 
• 383-63-1 ethyl trifluoroacetate, 
• 109463-66-3 N-TMS-4-Methoxy-2-methylaniline 
• 1200525-58-1 tert-butyl 2-(3,3,3-trifluoro-2-oxopropyl)-4-methoxyphenylcarbamate 
• 55414-72-7 (2-amino-5-methoxyphenyl)methanol 
• 76-05-1 trifluoroacetic acid 
• 1006-94-6 5-methoxylindole 
• 2926-29-6 Langlois reagent 

Relevant articles and documents

2-(Trifluoromethyl)indoles via Pd(0)-Catalyzed C(sp3)-H Functionalization of Trifluoroacetimidoyl Chlorides

Perfluoroalkylated indoles are valuable compounds in drug discovery. A Pd(0)-catalyzed C(sp3)-H functionalization enables access to 2-(trifluoromethyl)indoles from trifluoroacetimidoyl chlorides. These are stable compounds, easily obtained from

A New and Efficient One-Pot Synthesis of 2-Fluoroalkyl Substituted Indoles

A new simple and efficient one-pot synthesis of 2-fluoroalkyl substituted indoles from 2-aminobenzyl alcohols with fluorine-containing carboxylic acids in the presence of Ph3P, CCl4, and NEt3 is described. Various kinds of 2-fluoroalkyl substituted indole derivatives can be conveniently prepared.

Metal-free oxidative trifluoromethylation of indoles with CF3SO2Na on the C2 position

An efficient method of synthesizing 2-trifluoromethylindoles from indoles with easy-to-handle, cheap and low-toxic CF3SO2Na under metal-free conditions is described, which selectively introduces trifluoromethyl to indoles on the C2 position. The desired product can be obtained in 0.7 g yield. A radical intermediate may be involved in this transformation.

Bromotriphenylphosphonium salt promoted one-pot cyclization to 2-fluoroalkyl-substituted indoles

2-Fluoroalkyl-substituted indoles were prepared in moderate to excellent yields through bromotriphenylphosphonium salt promoted ring formation with fluorine-containing carboxylic acids in the presence of triethylamine in toluene at reflux temperature. A range of 2-fluoroalkyl-substituted indole derivatives can be conveniently prepared.

An efficient approach to 2-CF3-indoles based on ortho-nitrobenzaldehydes

The catalytic olefination reaction of 2-nitrobenzaldehydes with CF3 CCl3 afforded stereose-lectively trifluoromethylated ortho-nitrostyrenes in up to 88% yield. The reaction of these alkenes with pyrrolidine permits preparation of α-CF3-β-(2-nitroaryl) enamines. Subsequent one pot reduction of nitro-group by Fe-AcOH-H2 O system initiated intramolecular cyclization to afford 2-CF3-indoles. Target products can be prepared in up to 85% yields. Broad synthetic scope of the reaction was shown as well as some followed up transformations of 2-CF3-indole.

Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity

Methuosis is a form of nonapoptotic cell death characterized by an accumulation of macropinosome-derived vacuoles with eventual loss of membrane integrity. Small molecules inducing methuosis could offer significant advantages compared to more traditional anticancer drug therapies that typically rely on apoptosis. Herein we further define the effects of chemical substitutions at the 2-and 5-indolyl positions on our lead compound 3-(5-methoxy-2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propene-1-one (MOMIPP). We have identified a number of compounds that induce methuosis at similar potencies, including an interesting analogue having a hydroxypropyl substituent at the 2-position. In addition, we have discovered that certain substitutions on the 2-indolyl position redirect the mode of cytotoxicity from methuosis to microtubule disruption. This switch in activity is associated with an increase in potency as large as 2 orders of magnitude. These compounds appear to represent a new class of potent microtubule-active anticancer agents.

3-SUBSTITUTED-1H-INDOLE, 3-SUBSTITUTED-1H-PYRROLO[2,3-B]PYRIDINE AND 3-SUBSTITUTED-1H-PYRROLO[3,2-B]PYRIDINE COMPOUNDS, THEIR USE AS MTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES

The invention relates to 3-substituted-1H-indole, 3-substituted-1H-pyrrolo[2,3-b]pyridine, and 3-substituted-1H-pyrrolo[3,2-b]pyridine compounds of the Formula (I): or a pharmaceutically acceptable salt thereof, wherein the constituent variables are as defined herein, compositions comprising the compounds, and methods for making and using the compounds.

Fluorinated N-[2-(haloalkyl)phenyl]imidoyl chloride, a key intermediate for the synthesis of 2-fluoroalkyl substituted indole derivatives via Grignard cyclization process

Fluorinated N-[2-(haloalkyl)phenyl]imidoyl chloride, which was readily available from the corresponding anilines by using Uneyama's one-pot synthesis of fluorinated imidoyl chloride, was found to be a key intermediate for the facile synthesis of 2-fluoroa

Grignard cyclization reaction of fluorinated N-arylimidoyl chlorides: A novel and facile access to 2-fluoroalkyl indoles

2-Fluoroalkyl-substituted indole derivatives were simply prepared via the Grignard cyclization reaction (GCR) of corresponding fluorinated N-aryl imidoyl chlorides in good yields. This approach provides a novel and facile access to the biologically import

QUINAZOLINE DERIVATIVES AS ANGIOGENESIS INHIBITORS

The invention relates to the use of compounds of the formula I: wherein ring C is an 8, 9, 10, 12 or 13-membered bicyclic or tricyclic moiety which optionally may contain 1-3 heteroatoms selected independently from O, N and S; Z is -O-, -NH-, -S-, -CH2- or a direct bond; n is 0-5; m is 0-3; R represents hydrogen, hydroxy, halogeno, cyano, nitro, trifluoromethyl, C1-3alkyl, C1-3alkoxy, C1-3alkylsulphanyl, -NRR (wherein R and R, which may be the same or different, each represents hydrogen or C1-3alkyl), or RX- (wherein X and R are as defined herein; R represents hydrogen, oxo, halogeno, hydroxy, C1-4alkoxy, C1-4alkyl, C1-4alkoxymethyl, C1-4alkanoyl, C1-4haloalkyl, cyano, amino, C2-5alkenyl, C2-5alkynyl, C1-3alkanoyloxy, nitro, C1-4alkanoylamino, C1-4alkoxycarbonyl, C1-4alkylsulphanyl, C1-4alkylsulphinyl, C1-4alkylsulphonyl, carbamoyl, N-C1-4alkylcarbamoyl, N,N-di(C1-4alkyl)carbamoyl, aminosulphonyl, N-C1-4alkylaminosulphonyl, N,N-di(C1-4alkyl)aminosulphonyl, N-(C1-4alkylsulphonyl)amino, N-(C1-4alkylsulphonyl)-N-(C1-4alkyl)amino, N,N-di(C1-4alkylsulphonyl)amino, a C3-7alkylene chain joined to two ring C carbon atoms, C1-4alkanoylaminoC1-4alkyl, carboxy or a group RX (wherein X and R are as defined herein); and salts thereof, in the manufacture of a medicament for use in the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blooded animals, processes for the preparation of such compounds, pharmaceutical compositions containing a compound of formula I or a pharmaceutically acceptable salt thereof as active ingredient and compounds of formula I. The compounds of formula I and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.