67169-22-6 | 2-Methyl-4-(trifluoromethyl) aniline

CAS:67169-22-6 | 2-Methyl-4-(trifluoromethyl) aniline,Description

2-Methyl-4-(trifluoromethyl)aniline is a chemical compound that belongs to the trifluoromethylbenzene series. It is used as a reactant in the synthesis of various compounds.

Synthesis Analysis

The synthesis of 2-Methyl-4-(trifluoromethyl)aniline involves several steps. One method involves the reaction of the methyl ester of 2-chloronicotinic acid with 2-methyl-3-trifluoromethylaniline. Another method involves the reaction with triethylamine in ethyl acetate or water.

Molecular Structure Analysis

The molecular formula of 2-Methyl-4-(trifluoromethyl)aniline is C8H8F3N. The IUPAC Standard InChI is InChI=1S/C8H8F3N/c1-5-4-6(8(9,10)11)2-3-7(5)12/h2-4H,12H2,1H3.

Chemical Reactions Analysis

2-Methyl-4-(trifluoromethyl)aniline is used in various chemical reactions. For example, it is used in the synthesis of an analgesic compound, flunixin, via reaction with 2-chloronicotinate in ethylene glycol.

Scientific Research Applications

Application 1: Trifluoromethylarylation of Alkenes

• Summary of Application : This compound is used in the trifluoromethylarylation of alkenes. This process involves the simultaneous introduction of an aromatic and an aliphatic motif in a single step, a powerful transformation that is still underdeveloped.
• Methods of Application : The method allows the trifluoromethylarylation of alkenes using anilines, for the first time, with no need for additives, transition metals, photocatalysts or an excess of reagents. An in-depth mechanistic study reveals the key role of hexafluoroisopropanol (HFIP) as a unique solvent, establishing a hydrogen bonding network with aniline and trifluoromethyl reagent.
• Results or Outcomes : This work uncovers a new mode of reactivity that involves the use of abundant anilines as a non-prefunctionalized aromatic source and the simultaneous activation of trifluoromethyl hypervalent iodine reagent.

Application 2: Synthesis of Methylguanidine Derivatives

• Summary of Application : 2-Methyl-3-trifluoromethylaniline is a reactant in the synthesis of methylguanidine derivatives. These derivatives are prospective PET radioligands for the open channel of the NMDA receptor, which is linked to Alzheimer’s, epilepsy, and other neurodegenerative disorders.
• Methods of Application : The specific methods of application or experimental procedures were not detailed in the source.
• Results or Outcomes : The specific results or outcomes were not detailed in the source.

Application 3: Synthesis of Flunixin

• Summary of Application : 2-Methyl-3-(trifluoromethyl)aniline may be used in the synthesis of an analgesic compound, flunixin.
• Methods of Application : The compound reacts with 2-chloronicotinate in ethylene glycol to synthesize flunixin.
• Results or Outcomes : The specific results or outcomes were not detailed in the source.

Application 4: Synthesis of 4-(trialkylmethyl)anilines

• Summary of Application : 4-(Trifluoromethyl)aniline is used in the synthesis of 4-(trialkylmethyl)anilines. These compounds are important intermediates in organic synthesis.
• Methods of Application : The specific methods of application or experimental procedures were not detailed in the source.
• Results or Outcomes : The specific results or outcomes were not detailed in the source.

Application 5: Synthetic Building Block

• Summary of Application : 2-Methyl-4-(trifluoromethyl)aniline is used as a synthetic building block.
• Methods of Application : The specific methods of application or experimental procedures were not detailed in the source.
• Results or Outcomes : The specific results or outcomes were not detailed in the source.

Safety And Hazards

2-Methyl-4-(trifluoromethyl)aniline is considered hazardous. It can cause skin irritation, serious eye irritation, and may cause respiratory irritation. It is advised to handle this chemical with appropriate protective measures.

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