691877-03-9 | 3-Bromo-5-cyanobenzotrifluoride

CAS:691877-03-9 | 3-Bromo-5-cyanobenzotrifluoride,Description

3-Bromo-5-(trifluoromethyl)benzonitrile is a chemical compound that is part of a broader class of brominated and trifluoromethylated aromatic nitriles. These compounds are of interest due to their potential applications in organic synthesis and material science. They can serve as versatile starting materials for organometallic synthesis and are often used in the preparation of more complex molecules due to the reactivity of the bromo and nitrile groups.

Synthesis Analysis

The synthesis of related compounds often involves the selective halogenation of aromatic compounds. For instance, 1-Bromo-3,5-bis(trifluoromethyl)benzene, a compound with similar substituents, can be prepared by treating 1,3-bis(fluoromethyl)benzene with N,N'-dibromo-5,5-dimethylhydantoin in strongly acidic media. This method showcases the potential pathways that might be adapted for the synthesis of 3-Bromo-5-(trifluoromethyl)benzonitrile, although the specific synthesis details for this compound are not provided in the data.

Molecular Structure Analysis

While the exact molecular structure of 3-Bromo-5-(trifluoromethyl)benzonitrile is not detailed in the provided papers, related compounds exhibit interesting structural characteristics. For example, the crystal structure of o-(bromomethyl)benzonitrile shows that no angle in the benzyl ring significantly deviates from the mean, indicating a stable aromatic system. Similarly, the molecular structures of trifluoromethyltris(dialkylamino)phosphonium bromides, which contain the trifluoromethyl group, exhibit a distorted tetrahedral bond configuration. These insights suggest that 3-Bromo-5-(trifluoromethyl)benzonitrile would also display a stable aromatic ring with characteristic bond angles and lengths influenced by the presence of the bromo and trifluoromethyl substituents.

Chemical Reactions Analysis

The bromo and nitrile functional groups in 3-Bromo-5-(trifluoromethyl)benzonitrile suggest that it could participate in various chemical reactions. Brominated aromatic compounds are known to undergo nucleophilic substitution reactions, where the bromine atom can be replaced by other nucleophiles. Additionally, the nitrile group can be involved in reactions such as hydrolysis to form carboxylic acids or reduction to form primary amines. The reactivity of the trifluoromethyl group can also be leveraged in organometallic chemistry to introduce fluorinated substituents into target molecules.

Physical and Chemical Properties Analysis

The physical and chemical properties of 3-Bromo-5-(trifluoromethyl)benzonitrile would be influenced by its functional groups. The presence of the bromo group typically increases the density and boiling point of the compound due to its high atomic mass. The trifluoromethyl group is known to impart unique electronic properties due to its strong electron-withdrawing effect, which can affect the acidity of adjacent protons and the overall reactivity of the molecule. The nitrile group contributes to the compound's polarity and can enhance its solubility in polar solvents. However, specific data on the physical properties of 3-Bromo-5-(trifluoromethyl)benzonitrile are not provided in the papers.

Scientific Research Applications

Synthetic Processes and Organic Chemistry

3-Bromo-5-(trifluoromethyl)benzonitrile is involved in various synthetic processes and advancements in organic chemistry. For instance, Li et al. (2009) developed an efficient and nonchromatographic process for the production of compounds related to 3-Bromo-5-(trifluoromethyl)benzonitrile, demonstrating its significance in the scale-up production of complex organic molecules (Li et al., 2009). Similarly, Schlosser et al. (2006) explored the relay propagation of crowding in molecules containing the trifluoromethyl group, highlighting the unique steric and electronic properties of such compounds (Schlosser et al., 2006).

Organometallic Synthesis

In the field of organometallic synthesis, Porwisiak and Schlosser (1996) found that 1-Bromo-3,5-bis(trifluoromethyl)benzene, a compound closely related to 3-Bromo-5-(trifluoromethyl)benzonitrile, serves as a versatile starting material for synthesizing various organometallic intermediates (Porwisiak & Schlosser, 1996). This underscores the compound's role in the preparation of more complex organometallic structures.

Spectroelectrochemical Applications

A study by Kamiloğlu et al. (2018) involved the synthesis and investigation of spectroelectrochemical properties of compounds bearing the trifluoromethyl group, including analogs of 3-Bromo-5-(trifluoromethyl)benzonitrile. This research demonstrates the utility of such compounds in developing materials with specific electrochemical and spectroelectrochemical characteristics (Kamiloğlu et al., 2018) .

Catalysis and Reaction Mechanisms

Zhou et al. (2020) described the use of a related compound, 3-Bromo-1,1,1-trifluoroacetone, as an effective reagent in trifluoromethylation reactions to construct important molecular skeletons. This highlights the role of trifluoromethylated compounds in facilitating novel catalytic reactions and synthesizing bioactive molecules (Zhou et al., 2020).

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