328-74-5 | 3,5-Bis(trifluoromethyl)aniline

CAS:328-74-5 | 3,5-Bis(trifluoromethyl)aniline,Description

3,5-Bis(trifluoromethyl)aniline is a chemical compound that has been the subject of various studies due to its interesting properties and potential applications. It is a derivative of aniline where two trifluoromethyl groups are substituted at the 3 and 5 positions of the benzene ring. This compound serves as a building block in the synthesis of various complex molecules and materials, including pharmaceuticals, agrochemicals, and polymers.

Synthesis Analysis

The synthesis of 3,5-bis(trifluoromethyl)aniline and its derivatives has been explored in several studies. A convenient synthesis method for N,N-bis(trifluoromethyl)anilines involves dediazotation reactions of aryldiazoniumbis(trifluoromethyl)imides with CuI salts. Another study reports the synthesis of 3,5-bis(trifluoromethyl)aniline derivatives through a two-step process starting from commercially available 3,5-bis(trifluoromethyl)benzylamine. Additionally, a method for synthesizing 3,5-bis(trifluoromethyl)salicylic acid, an important intermediate, from 2-bromo-3,5-bis(trifluoromethyl)aniline has been described.

Molecular Structure Analysis

The molecular structure of 3,5-bis(trifluoromethyl)aniline derivatives has been determined using various spectroscopic and crystallographic techniques. For instance, the molecular structure of a novel Schiff base derived from 3,5-bis(trifluoromethyl)aniline was determined using X-ray single-crystal data and compared with theoretical calculations. The study of acyclic sulfur-nitrogen compounds also provides insights into the molecular structures of related compounds, highlighting the role of electron delocalization.

Chemical Reactions Analysis

3,5-Bis(trifluoromethyl)aniline participates in various chemical reactions, forming a wide range of products. It reacts with alkoxybenzenes and anilines to form vinylogous trifluoroacetylation products and bis(trifluoromethyl)quinolines. The compound also serves as a precursor for the synthesis of polyimides with desirable properties such as high thermal stability and low dielectric constants. Furthermore, reactions with primary amines have been shown to produce 4-substituted-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles.

Physical and Chemical Properties Analysis

The physical and chemical properties of 3,5-bis(trifluoromethyl)aniline derivatives have been extensively studied. For example, the Schiff base derived from this compound and its metal complexes have been investigated for their antimicrobial activities, DNA binding and cleavage abilities, and potential as anti-cancer agents. Polyimides synthesized from derivatives of 3,5-bis(trifluoromethyl)aniline exhibit excellent solubility, high glass-transition temperatures, and low water absorption. The physical properties of ionic liquids containing related anions have also been reported, providing valuable data on phase-transition temperatures, densities, and other relevant parameters.

Scientific Research Applications

• Synthesis of Schiff’s Base

  • Application Summary: 3,5-Bis(trifluoromethyl)aniline is used in the synthesis of N-[2-hydroxy-1-naphthylidene]-3,5-bis(trifluoromethyl)aniline, a type of Schiff’s base.

• Synthesis of 5,7-Bis(trifluoromethyl)aniline

  • Application Summary: 3,5-Bis(trifluoromethyl)aniline is used in the synthesis of 5,7-bis(trifluoromethyl)aniline.

• Synthesis of Organocatalyst

  • Application Summary: 3,5-Bis(trifluoromethyl)aniline is used in the synthesis of N,N′-bis[3,5-bis(tri-fluoromethyl)phenyl]thiourea, an organocatalyst.

• Use as a Directing Group in Palladium-Catalyzed Cross-Coupling

  • Application Summary: 3,5-Bis(trifluoromethyl)aniline was found to be a highly efficient monodentate transient directing group (MonoTDG) for the palladium-catalyzed direct dehydrogenative cross-coupling of benzaldehydes with arenes.

• Synthesis of N-1-Phenylethyl-3,5-bis(trifluoromethyl)aniline

  • Application Summary: 3,5-Bis(trifluoromethyl)aniline is used in the synthesis of N-1-phenylethyl-3,5-bis(trifluoromethyl)aniline via a titanium-catalyzed hydroamination reaction.

• Use as a Directing Group in Palladium-Catalyzed Cross-Coupling

  • Application Summary: 3,5-Bis(trifluoromethyl)aniline was found to be a highly efficient monodentate transient directing group (MonoTDG) for the palladium-catalyzed direct dehydrogenative cross-coupling of benzaldehydes with arenes.

• Synthesis of 3,5-Bis(trifluoromethyl)phenyl Isothiocyanate

  • Application Summary: 3,5-Bis(trifluoromethyl)aniline can be used in the synthesis of 3,5-Bis(trifluoromethyl)phenyl isothiocyanate.

• Synthesis of 3,5-Bis(trifluoromethyl)benzylamine

  • Application Summary: 3,5-Bis(trifluoromethyl)aniline can be used in the synthesis of 3,5-Bis(trifluoromethyl)benzylamine.

Safety And Hazards

This chemical is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It has acute oral toxicity, acute dermal toxicity, and acute inhalation toxicity. It can cause skin corrosion/irritation and serious eye damage/eye irritation. It has specific target organ toxicity (single exposure) with the target organs being the respiratory system.

Future Directions

3,5-Bis(trifluoromethyl)aniline has been found to be a highly efficient monodentate transient directing group (MonoTDG) for the palladium-catalyzed direct dehydrogenative cross-coupling of benzaldehydes with arenes. This suggests that it could have potential applications in the field of organic synthesis.

Relevant Papers

Relevant papers on 3,5-Bis(trifluoromethyl)aniline can be found in various journals. These papers cover a wide range of topics including its synthesis, properties, and applications.

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