289686-70-0 | 2-(3,5-bis(trifluoroMethyl)phenyl)-2-Methyl propanoic acid

CAS:289686-70-0 | 2-(3,5-bis(trifluoroMethyl)phenyl)-2-Methyl propanoic acid,Description

2-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoic acid is a compound that features a phenyl ring substituted with two trifluoromethyl groups at the 3 and 5 positions, and a 2-methylpropanoic acid moiety. This structure suggests that the compound could exhibit unique physical and chemical properties due to the presence of the electron-withdrawing trifluoromethyl groups, which could affect its reactivity and interaction with other molecules.

Synthesis Analysis

The synthesis of compounds related to 2-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoic acid can be complex due to the presence of trifluoromethyl groups. For instance, the synthesis of tris[3,5-bis(trifluoromethyl)phenyl]borane, a related compound, has been achieved on a practical scale, indicating the feasibility of synthesizing complex molecules with multiple trifluoromethyl substituents. Additionally, the preparation of 3,5-bis(trifluoromethyl)phenyl sulfones for use in the Julia-Kocienski olefination reaction suggests that the trifluoromethylated phenyl ring can be incorporated into various molecular frameworks.

Molecular Structure Analysis

The molecular structure of 2-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoic acid is likely to be influenced by the trifluoromethyl groups, which are known to be highly electron-withdrawing. This can lead to a decrease in electron density on the phenyl ring and potentially affect the acidity of the propanoic acid moiety. The presence of these groups can also impact the overall molecular geometry and electronic distribution.

Chemical Reactions Analysis

Compounds with 3,5-bis(trifluoromethyl)phenyl groups have been shown to participate in various chemical reactions. For example, 3,5-bis(trifluoromethyl)phenylboronic acid has been used as a catalyst in dehydrative amidation reactions, and 3,5-bis(trifluoromethyl)phenyl sulfones have been employed in the Julia-Kocienski olefination reaction. These studies demonstrate the reactivity of the trifluoromethylated phenyl ring in different chemical contexts.

Physical and Chemical Properties Analysis

The physical and chemical properties of 2-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoic acid are not directly reported in the provided papers. However, the properties of related compounds suggest that the trifluoromethyl groups would confer high stability and potentially affect the compound's solubility and boiling point. For instance, fluorinated polyimides derived from a diamine containing a 3,5-bis(trifluoromethyl)phenyl group exhibit good solubility and thermal stability. The electron-withdrawing nature of the trifluoromethyl groups could also influence the acidity of the propanoic acid moiety, making it a stronger acid compared to its non-fluorinated analogs.

Scientific Research Applications

• Antibacterial Drug Development

  • Field: Medicinal Chemistry
  • Application: The compound is used in the synthesis of pyrazole derivatives, which have shown potential as growth inhibitors of drug-resistant bacteria.
  • Method: The designed compounds were synthesized by the reaction of 3′,5′-bis (trifluoromethyl)acetophenone with 4-hydrazinobenzoic acid to form the hydrazone intermediate, which on reaction with the Vilsmeier-Haack reagent formed the pyrazole aldehyde.
  • Results: Most of the synthesized compounds are potent growth inhibitors of planktonic Gram-positive bacteria with minimum inhibitory concertation (MIC) values as low as 0.25 µg/mL.

• Organic Light-Emitting Diodes (OLEDs)

  • Field: Material Science
  • Application: The compound is used in the synthesis of iridium complexes, which are used as emitters in OLEDs.
  • Method: The iridium complexes were synthesized using 2-(3,5-bis(trifluoromethyl)phenyl)pyrimidine and 2-(3,5-bis(trifluoromethyl)phenyl)-5-fluoropyrimidine as the main ligands and 2,4-pentanedionate as the ancillary ligands.
  • Results: The OLEDs using these emitters exhibited good performances. Especially, the device using Ir(tfmphpm)2(tpip) displayed the best performances with a maximum luminance of 28,194 cd m−2, a maximum current efficiency of 74.70 cd A−1, and a maximum external quantum efficiency up to 35.0%.

• Catalyst Development

  • Field: Organic Chemistry
  • Application: The compound is used in the synthesis of N,N′-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea, a key catalyst in organic transformations.
  • Method: The catalyst is synthesized using 3,5-bis(trifluoromethyl)phenyl motifs and is used extensively in promoting organic transformations.
  • Results: The catalyst has played a very important role in the development of H-bond organocatalysts.

• Synthesis of Methylene-Arylbutenones

  • Field: Organic Chemistry
  • Application: The compound is used in the synthesis of methylene-arylbutenones via carbonylative arylation of allenols.
  • Method: The synthesis involves the reaction of 3,5-bis(trifluoromethyl)phenylboronic acid with allenols.
  • Results: The reaction leads to the formation of methylene-arylbutenones.

• Synthesis of Primary Amino Acid Derivatives

  • Field: Medicinal Chemistry
  • Application: The compound is used in the synthesis of primary amino acid derivatives with anticonvulsant activity.
  • Method: The synthesis involves the reaction of 3,5-bis(trifluoromethyl)phenylboronic acid with appropriate reagents.
  • Results: The reaction leads to the formation of primary amino acid derivatives.

• Determination of Ionic Perfluorinated Substances

  • Field: Environmental Chemistry
  • Application: The compound is used as a building block to synthesize the pentaamine and bis-heterocyclic libraries in determination of ionic perfluorinated substances and telomers in leachates from landfills and sediment samples.
  • Method: The synthesis involves the reaction of 3,5-bis(trifluoromethyl)phenylacetic acid with appropriate reagents.
  • Results: The reaction leads to the formation of pentaamine and bis-heterocyclic libraries.

• Catalyst Development

  • Field: Organic Chemistry
  • Application: The compound is used in the synthesis of N,N′-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea, a key catalyst in organic transformations.
  • Method: The catalyst is synthesized using 3,5-bis(trifluoromethyl)phenyl motifs and is used extensively in promoting organic transformations.
  • Results: The catalyst has played a very important role in the development of H-bond organocatalysts.

• Synthesis of Methylene-Arylbutenones

  • Field: Organic Chemistry
  • Application: The compound is used in the synthesis of methylene-arylbutenones via carbonylative arylation of allenols.
  • Method: The synthesis involves the reaction of 3,5-bis(trifluoromethyl)phenylboronic acid with allenols.
  • Results: The reaction leads to the formation of methylene-arylbutenones.

• Synthesis of Primary Amino Acid Derivatives

  • Field: Medicinal Chemistry
  • Application: The compound is used in the synthesis of primary amino acid derivatives with anticonvulsant activity.
  • Method: The synthesis involves the reaction of 3,5-bis(trifluoromethyl)phenylboronic acid with appropriate reagents.
  • Results: The reaction leads to the formation of primary amino acid derivatives.

• Determination of Ionic Perfluorinated Substances

  • Field: Environmental Chemistry
  • Application: The compound is used as a building block to synthesize the pentaamine and bis-heterocyclic libraries in determination of ionic perfluorinated substances and telomers in leachates from landfills and sediment samples.
  • Method: The synthesis involves the reaction of 3,5-bis(trifluoromethyl)phenylacetic acid with appropriate reagents.
  • Results: The reaction leads to the formation of pentaamine and bis-heterocyclic libraries.

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