172217-02-6

Basic information

• Product Name: 7-(trifluoromethyl)-1H-indole
• Synonyms: 7-(trifluoromethyl)-1H-indole;1H-Indole, 7-(trifluoromethyl)-;7-(Trifluoromethyl)
• CAS NO: 172217-02-6
• Molecular Formula: C₉H₆F₃N
• Molecular Weight: 185.15
• Mol File: 172217-02-6.mol

Chemical Properties

• Boiling Point: 256.676°C at 760 mmHg
• Flash Point: 109.034°C
• Appearance: /
• Density: 1.368g/cm³
• Vapor Pressure: 0.024mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.16±0.30(Predicted)
• CAS DataBase Reference: 7-(trifluoromethyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(trifluoromethyl)-1H-indole(172217-02-6)
• EPA Substance Registry System: 7-(trifluoromethyl)-1H-indole(172217-02-6)

Safety Data

• Hazardous Substances Data: 172217-02-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-(trifluoromethyl)-1H-indole is used as a building block in the development of new pharmaceutical drugs. Its unique structure and potential pharmacological properties make it a promising candidate for the creation of novel therapeutic agents.
Used in Organic Synthesis:
7-(trifluoromethyl)-1H-indole is used as a key intermediate in organic synthesis, allowing for the construction of more complex molecules with potential applications in various fields.
Used in Anticancer Research:
7-(trifluoromethyl)-1H-indole is studied for its potential as an anticancer agent. Its ability to modulate various biological pathways and target specific cancer cells makes it a valuable compound in the search for new cancer treatments.
Used in Serotonin Receptor Modulation:
7-(trifluoromethyl)-1H-indole has been investigated for its potential to modulate serotonin receptors. This property could be harnessed in the development of drugs targeting neurological and psychiatric disorders.
Used in Drug Discovery:
Due to its unique structure and potential medicinal applications, 7-(trifluoromethyl)-1H-indole is of interest to researchers in the fields of organic chemistry and drug discovery. It serves as a starting point for the exploration of new chemical entities with therapeutic potential.

InChI:InChI=1/C9H6F3N/c10-9(11,12)7-3-1-2-6-4-5-13-8(6)7/h1-5,13H

Upstream product

• 172216-98-7 7-(trifluoromethyl)-1H-indole-2-carboxylic acid 
• 384-22-5 2-nitrobenzotrifluoride 
• 1826-67-1 vinyl magnesium bromide 
• 120-72-9 indole 
• 887144-94-7 Togni's reagent II 
• 154422-28-3 ethyl 7-(trifluoromethyl)-1H-indole-2-carboxylate 

Downstream Products

• 172216-99-8 7-(trifluoromethyl)indole-3-carboxaldehyde 

Relevant articles and documents

Redox-ligand sustains controlled generation of CF3 radicals by well-defined copper complex

A well-defined copper complex bearing iminosemiquinone ligands performs single electron reduction of an electrophilic CF3+ source into CF3 radicals. This redox behavior is enabled by the ligand which shuttles through two different redox states (iminosemiquinone and iminobenzoquinone) while the copper center is preserved as a Cu(ii). This system was used in the trifluoromethylation of silyl enol ethers, heteroaromatics and in the hydrotrifluoromethylation of alkynes. This is the first example of cooperative redox catalysis for the controlled generation of CF3 radicals.

Iron-catalyzed trifluoromethylation of enamide

Herein the first example of the iron(II)-catalyzed trifluoromethylation of enamide using mild and simple reaction conditions is reported. The method is cost-effective and uses the easy-to-handle Togni's reagent as the electrophilic CF3 source. This transformation is totally regioselective at the C3 position of enamides and exhibits broad substrate scope, good functional group tolerance and thus demonstrates its useful application in a late-stage fluorination strategy.

Synthesis of novel indole derivatives: Variations in the Bartoli reaction

The synthesis of a range of novel substituted indoles and tricyclic indole derivatives is described using an extension of the Bartoli methodology.

Fischer indolization of ethyl pyruvate 2-[2- (trifluoromethyl)phenyl]phenylhydrazone and new insight into the mechanism of the Goldberg reaction. (Fischer indolization and its related compounds. XXVI)

The Fischer indolization of ethyl pyruvate 2-[2- (trifluoromethyl)phenyl]phenylhydrazone (5) gave two indolic products, ethyl 7-(trifluoromethyl)-1-phenylindole-2-carboxylate (12) as a minor product and ethyl 1-[2-(trifluoromethyl)phenyl]indole-2-carboxylate (13) as a major product. This result shows that the Fischer indolization occurred on the more electron-rich phenyl group. In the Goldberg reaction to prepare 13 from ethyl indole-2-carboxylate (15) and o- (21) or m-bromo-α,α,α-trifluorotoluene (23), it was found that Goldberg reaction proceeds via a benzyne mechanism, at least in part, in a sterically crowded situation.