Product Introduction of 4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-(trifluoromethyl)aniline (CAS 1207314-85-9)
4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-(trifluoromethyl)aniline, with the CAS number 1207314-85-9, is a significant chemical compound in the field of organic chemistry. This compound has unique chemical and physical properties that make it useful in various applications. In this article, we will delve into its detailed introduction, properties, uses, applications in different fields, and preparation methods.
Product Overview
The chemical 4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-(trifluoromethyl)aniline is an aniline derivative. The presence of multiple fluorine atoms in its structure imparts it with some special characteristics. Fluorine-containing compounds often exhibit enhanced stability, lipophilicity, and biological activity, which are crucial factors in many chemical and pharmaceutical applications. The aniline group provides a reactive site for further chemical modifications, making it a valuable building block in organic synthesis.
Physical and Chemical Properties
Physical Properties
The physical state of 4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-(trifluoromethyl)aniline is typically a liquid or a solid, depending on the specific conditions. Its melting point and boiling point are influenced by the molecular structure and intermolecular forces. Due to the presence of fluorine atoms, which are highly electronegative, the compound may have relatively low surface tension and good solubility in some organic solvents. The density of this compound is also affected by its molecular weight and the packing of molecules in the solid or liquid phase.
Chemical Properties
Chemically, the aniline group in 4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-(trifluoromethyl)aniline is prone to electrophilic aromatic substitution reactions. The amino group (-NHâ‚‚) can act as a nucleophile and react with various electrophiles. The fluorine atoms on the heptafluoropropyl and trifluoromethyl groups are relatively stable but can influence the reactivity of the adjacent aromatic ring through inductive and resonance effects. For example, the electron-withdrawing nature of fluorine atoms can make the aromatic ring less electron-rich, affecting the rate and selectivity of substitution reactions.
Uses and Applications
Pharmaceutical Industry
In the pharmaceutical industry, 4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-(trifluoromethyl)aniline can be used as a key intermediate in the synthesis of new drugs. The unique combination of fluorine atoms and the aniline group can endow the final drug molecule with improved pharmacokinetic and pharmacodynamic properties. For instance, fluorine substitution can increase the metabolic stability of drugs, reduce their susceptibility to enzymatic degradation, and enhance their binding affinity to target proteins. Some potential therapeutic areas where this compound may find application include anti – cancer, anti – inflammatory, and anti – microbial drug development. The aniline moiety can be further functionalized to introduce other pharmacophoric groups, leading to the discovery of novel drug candidates.
Agrochemical Industry
In the agrochemical field, this compound can be utilized in the synthesis of pesticides and herbicides. The fluorine – containing groups can enhance the biological activity of the agrochemical products. For example, they can improve the penetration of the active ingredients into plant tissues, increase the durability of the pesticides on the plant surface, and enhance the selectivity towards pests or weeds. The aniline group can be used to modify the structure of the agrochemicals to optimize their efficacy and safety profiles. Some possible applications include the development of new insecticides that target specific insect pests or herbicides that can selectively control weeds in agricultural fields.
Material Science
In material science, 4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-(trifluoromethyl)aniline can be incorporated into polymers to improve their performance. Fluorine – containing polymers often have excellent chemical resistance, low surface energy, and good thermal stability. By introducing this compound into polymer chains, the resulting polymers can be used in applications such as coatings, adhesives, and membranes. For example, in coating applications, the fluorine – rich polymers can provide a protective layer with anti – fouling, anti – corrosion, and water – repellent properties. In membrane applications, they can be used for gas separation or water purification due to their unique permeability and selectivity properties.
Preparation Methods
Method 1: Aromatic Nucleophilic Substitution
One possible preparation method involves aromatic nucleophilic substitution reactions. First, a suitable aromatic precursor with a leaving group (such as a halogen) at the appropriate position is selected. Then, a nucleophile containing the 1,1,1,2,3,3,3 – heptafluoropropan – 2 – yl and trifluoromethyl groups is reacted with the aromatic precursor in the presence of a base. The reaction conditions, such as temperature, solvent, and reaction time, need to be carefully controlled to ensure high yield and selectivity. For example, a polar aprotic solvent like dimethylformamide (DMF) may be used to facilitate the reaction, and the base can be an inorganic base such as potassium carbonate.
Method 2: Reduction of Nitro Compounds
Another approach is to start with a nitro – substituted aromatic compound containing the 1,1,1,2,3,3,3 – heptafluoropropan – 2 – yl and trifluoromethyl groups. The nitro group can be reduced to an amino group using a reducing agent. Common reducing agents include metal – based reducing agents such as iron in the presence of an acid (e.g., hydrochloric acid) or catalytic hydrogenation using a metal catalyst like palladium on carbon (Pd/C) under hydrogen gas atmosphere. The choice of reducing agent depends on the specific reaction conditions and the stability of the other functional groups in the molecule.
References
- Fluorinated Aromatic Amines in Drug Discovery (ACS Publications, 2021)
- Environmental Applications of Fluorochemicals (Chemosphere, 2022)
- Synthesis of Fluorinated Aniline Derivatives (US Patent, 2023)