41731-39-9 | 2-BroMo-4-(trifluoroMethyl)thiazole

CAS:41731-39-9 | 2-BroMo-4-(trifluoroMethyl)thiazole,Description

2-Bromo-4-(trifluoromethyl)thiazole is a compound that has garnered interest due to its potential applications in various fields, including drug discovery and material science. The presence of both bromine and trifluoromethyl groups in the thiazole ring suggests that this compound could serve as a versatile intermediate for further chemical transformations.

Synthesis Analysis

The synthesis of thiazole derivatives, including those with bromo and trifluoromethyl substituents, has been explored in several studies. For instance, a synthetic protocol involving 1,3-dibromo-1,1-difluoro-2-propanone as a synthon has been reported, which allows the introduction of a bromodifluoromethyl group into the thiazole ring. Another study describes the selective bromination of thiazole derivatives using N-bromosuccinimide, which could potentially be applied to synthesize 2-bromo-4-(trifluoromethyl)thiazole. Additionally, the synthesis of related compounds with trifluoromethyl groups has been achieved through various methods, including one-pot, three-component reactions.

Molecular Structure Analysis

Structural and conformational studies of thiazole derivatives are crucial for understanding their chemical behavior. Spectroscopic methods such as FT-IR, NMR, Raman, and X-ray diffraction have been employed to elucidate the structures of these compounds. Density functional theory (DFT) calculations can also assist in predicting the vibrational and magnetic properties, providing a deeper insight into the molecular structure.

Chemical Reactions Analysis

Thiazole derivatives undergo a range of chemical reactions, which can be utilized to synthesize complex molecules of biological interest. For example, the bromination of acrylonitriles proceeds regioselectively at the thiazole ring, leading to the formation of new brominated thiazoles. The reactivity of the thiazole ring towards electrophilic substitution reactions, such as bromination, is influenced by the nature and position of substituents on the ring.

Physical and Chemical Properties Analysis

The physical and chemical properties of thiazole derivatives are influenced by their molecular structure. The presence of electron-withdrawing groups such as trifluoromethyl can affect the electron density distribution within the molecule, which in turn can influence properties like acidity, reactivity, and stability. The synthesis of novel organic compounds derived from thiazole derivatives and their characterization through various analytical techniques can provide valuable information about their physical properties, such as optical band gaps and dielectric constants.

Scientific Research Applications

Synthesis and Reactivity

2-Bromo-4-(trifluoromethyl)thiazole demonstrates significant versatility in chemical reactions. It's used in the synthesis of diverse compounds due to its reactivity with various electrophiles. For example, the treatment of 2-trifluoroacetamido-4-(trifluoromethyl)thiazole with n-butyllithium produces a dianion that reacts with different electrophiles, leading to a variety of compounds, including aldehydes, ketones, chloroformates, acid chlorides, phosphorus oxychloride, silicon chloride, and disulfides (South & Van Sant, 1991) . This demonstrates its potential for creating structurally diverse molecules.

Application in Bioactive Compound Synthesis

The compound is also pivotal in synthesizing biologically interesting scaffolds. An efficient method has been developed for synthesizing 2-imino-4-(trifluoromethyl)thiazolidin-4-ol derivatives through a one-pot, three-component reaction. These reactions involve primary amines, aryl isothiocyanates, and 3-bromo-1,1,1-trifluoropropanone, leading to compounds like isoxazoles, triazoles, and propargylamine derivatives, which are of great interest in drug discovery (Dalmal et al., 2014).

Role in Novel Synthon Creation

In another study, 1,3-dibromo-1,1-difluoro-2-propanone, a novel synthon, was used in reactions with aromatic amines and sodium thiocyanate to create thiazoles. This process is particularly valuable in drug discovery programs, highlighting the utility of 2-Bromo-4-(trifluoromethyl)thiazole derivatives in medicinal chemistry (Colella et al., 2018).

Use in Azo Dye Synthesis

The versatility of 2-Bromo-4-(trifluoromethyl)thiazole extends to the synthesis of azo dyes. Reactions involving this compound have led to the creation of azo dyes, with studies focusing on the absorption maxima of the resulting products (Tanaka et al., 1991). This illustrates its potential in the field of color chemistry and materials science.

Safety And Hazards

The compound is considered hazardous and has been assigned the signal word "Warning". Hazard statements include H302 (Harmful if swallowed), H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). Precautionary measures include avoiding dust formation, avoiding breathing mist, gas or vapors, avoiding contact with skin and eyes, and using personal protective equipment.

Future Directions

While specific future directions for 2-Bromo-4-(trifluoromethyl)thiazole are not mentioned in the search results, thiazole derivatives are a topic of ongoing research due to their diverse biological activities. Further studies could focus on exploring the potential applications of 2-Bromo-4-(trifluoromethyl)thiazole in various fields, including medicinal chemistry.

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