Production Method 1

109-94-4

328-73-4

96617-71-9

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  30 min, -78 °C
1.2 3 h, -78 °C
1.3 Reagents: Potassium carbonate ,  Iodine Solvents: Ethanol ;  -78 °C; 16 h, rt
1.4 Reagents: Sodium sulfite Solvents: Water ;  rt

Reference

Facile preparation of aromatic esters from aromatic bromides with ethyl formate or DMF and molecular iodine via aryllithium

Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo, Tetrahedron, 2012, 68(24), 4701-4709

Production Method 2

725-89-3

96617-71-9

Reaction Conditions

Reference

Reductive carboxylation of aromatic esters by electron transfer from magnesium metal

Maekawa, Hirofumi; Okawara, Hikaru; Murakami, Taro, Tetrahedron Letters, 2017, 58(3), 206-209

Production Method 3

109-94-4

328-73-4

96617-71-9

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  30 min, -78 °C
1.2 3 h, -78 °C
1.3 Reagents: Potassium carbonate ,  Iodine ;  16 h, rt

Reference

One-pot preparation of aromatic ester or amide compounds from aromatic compounds, formic acid esters or formamide compounds, and alcohols or amines

, Japan, , ,

Production Method 4

725-89-3

96617-71-9

Reaction Conditions

1.1 Reagents: Sulfuric acid ;  10 h, reflux

Reference

Infrared absorption compound, resin composition, optical film, infrared cut filter, image sensor with good heat resistance

, Japan, , ,

Ethyl 3,5-bis(trifluoromethyl)benzoate Raw materials

• Ethyl formate
• 3,5-Bis(trifluoromethyl)benzoic acid
• 1-Iodo-3,5-bis(trifluoromethyl)-benzene

Ethyl 3,5-bis(trifluoromethyl)benzoate Preparation Products

• Ethyl 3,5-bis(trifluoromethyl)benzoate (96617-71-9)

• 1. An artificial photosynthesis system comprising a covalent triazine framework as an electron relay facilitator for photochemical carbon dioxide reduction?
  Siquan Zhang,Shengyao Wang,Liping Guo,Hao Chen,Bien Tan,Shangbin Jin J. Mater. Chem. C, 2020,8, 192-200
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  Christian K. Rank,Alexander W. Jones,Tatjana Wall,Patrick Di Martino-Fumo,Sarah Schr?ck,Markus Gerhards,Frederic W. Patureau Chem. Commun., 2019,55, 13749-13752
• 3. An all-solid-state imprinted polymer-based potentiometric sensor for determination of bisphenol S?
  Rongning Liang,Tanji Yin,Ruiqing Yao,Wei Qin RSC Adv., 2016,6, 73308-73312
• 4. An approach to asymmetric synthesis of β-aryl alanines by Pd(0)-catalyzed cross-coupling and cyanate-to-isocyanate rearrangement?
  Piotr Szcze?niak,Sebastian Stecko RSC Adv., 2015,5, 30882-30888
• 5. An alternative biorefinery approach to address microalgal seasonality: blending with spent coffee grounds
  Andre Prates Pereira,Tao Dong,Eric P. Knoshaug,Nick Nagle,Ryan Spiller,Bonnie Panczak,Christopher J. Chuck,Philip T. Pienkos Sustainable Energy Fuels, 2020,4, 3400-3408

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acid esters
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Benzoic acid esters

Ethyl 3,5-bis(trifluoromethyl)benzoate (CAS No. 96617-71-9): A Comprehensive Overview

Ethyl 3,5-bis(trifluoromethyl)benzoate, identified by the chemical compound code CAS No. 96617-71-9, is a significant molecule in the realm of organic chemistry and pharmaceutical research. This compound, characterized by its unique structural features, has garnered attention due to its potential applications in various scientific domains. The presence of multiple trifluoromethyl groups in its molecular structure imparts distinct properties that make it a subject of extensive study and interest.

The chemical structure of Ethyl 3,5-bis(trifluoromethyl)benzoate consists of a benzoate core substituted with two trifluoromethyl groups at the 3rd and 5th positions, linked to an ethyl ester moiety. This configuration endows the compound with enhanced lipophilicity and metabolic stability, making it a valuable candidate for further exploration in drug development. The trifluoromethyl groups are particularly noteworthy as they can influence the pharmacokinetic and pharmacodynamic properties of associated molecules, potentially improving their efficacy and selectivity.

In recent years, Ethyl 3,5-bis(trifluoromethyl)benzoate has been extensively studied for its role in synthesizing novel pharmaceutical intermediates. Researchers have leveraged its structural framework to develop compounds with improved bioavailability and reduced toxicity. The benzoate moiety is a well-known pharmacophore in medicinal chemistry, often found in drugs targeting neurological disorders, cardiovascular diseases, and inflammatory conditions. The introduction of trifluoromethyl groups further enhances these properties by increasing the metabolic stability and binding affinity to biological targets.

One of the most compelling aspects of Ethyl 3,5-bis(trifluoromethyl)benzoate is its potential application in the development of agrochemicals. The compound's structural robustness and resistance to degradation make it an excellent precursor for creating advanced pesticides and herbicides. These derivatives are designed to be more effective against resistant strains of pests while maintaining environmental safety. The use of trifluoromethyl groups in such applications enhances the compounds' persistence and efficacy, ensuring prolonged activity in agricultural settings.

The synthesis of Ethyl 3,5-bis(trifluoromethyl)benzoate involves multi-step organic reactions that require precise control over reaction conditions. Advanced synthetic methodologies have been developed to optimize yield and purity, ensuring that the final product meets stringent quality standards. Techniques such as palladium-catalyzed cross-coupling reactions and fluorination processes are commonly employed to introduce the necessary functional groups efficiently. These synthetic strategies highlight the compound's importance in industrial chemistry and its potential for large-scale production.

Recent studies have also explored the spectroscopic and thermal properties of Ethyl 3,5-bis(trifluoromethyl)benzoate. Nuclear magnetic resonance (NMR) spectroscopy has been particularly useful in elucidating its molecular structure, while mass spectrometry provides insights into its fragmentation patterns. These analytical techniques are crucial for confirming the identity and purity of the compound before it is used in further research or industrial applications.

The compound's thermal stability has been a focal point of investigation due to its potential use in high-temperature environments. Differential scanning calorimetry (DSC) studies have demonstrated that Ethyl 3,5-bis(trifluoromethyl)benzoate exhibits high melting points and decomposition temperatures, indicating its robustness under extreme conditions. This property makes it suitable for applications where thermal resistance is essential, such as in specialized coatings or high-performance materials.

Ethyl 3,5-bis(trifluoromethyl)benzoate also plays a role in materials science research. Its unique electronic properties make it a candidate for developing organic semiconductors and conductive polymers. These materials are integral to modern electronics, including flexible displays and solar cells. The incorporation of trifluoromethyl groups can modulate electron delocalization within the molecular framework, enhancing charge transport properties essential for efficient electronic devices.

The environmental impact of Ethyl 3,5-bis(trifluoromethyl)benzoate is another area of concern that has been addressed through rigorous toxicological studies. Researchers have evaluated its biodegradability and ecotoxicity to ensure that its use does not pose significant risks to ecosystems. These assessments are part of broader efforts to develop sustainable chemical alternatives that minimize environmental harm while maintaining efficacy.

In conclusion, Ethyl 3,5-bis(trifluoromethyl)benzoate (CAS No. 96617-71-9) is a versatile compound with diverse applications across multiple scientific disciplines. Its unique structural features, particularly the presence of multiple trifluoromethyl groups, contribute to its utility in pharmaceuticals, agrochemicals, materials science, and environmental chemistry. Ongoing research continues to uncover new possibilities for this compound, reinforcing its significance as a key player in modern chemical innovation.

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