351003-46-8 | 3-BROMO-5-(TRIFLUOROMETHYL)BENZENESULFONYL CHLORIDE

CAS:351003-46-8 | 3-BROMO-5-(TRIFLUOROMETHYL)BENZENESULFONYL CHLORIDE,Description

Synthesis Analysis

The synthesis of related compounds involves multi-step processes that include regioselective lithiation, electrophilic substitution, copper-catalyzed C–O coupling, and chloroxidation conditions. For instance, the synthesis of a key building block of penoxsulam starts from commercially available 3-bromobenzotrifluoride, which is structurally similar to the compound of interest. The synthesis of 3,5-bis(trifluoromethyl)benzoyl chloride, another related compound, involves bromination, carboxylation, and chlorination steps. These methods suggest that the synthesis of 3-Bromo-5-(trifluoromethyl)benzenesulfonyl chloride could potentially involve similar strategies, such as selective bromination and subsequent introduction of the sulfonyl chloride group.

Molecular Structure Analysis

The molecular structure of benzenesulfonyl chloride derivatives is characterized by the planarity of the benzene ring and the dihedral angle formed with the sulfonyl chloride group. For example, 2,4,5-trichlorobenzenesulfonyl chloride has been studied using X-ray diffraction, revealing a planar benzene ring and a dihedral angle of 66.0(5)° with the C(1)-S(1)-Cl(1) plane. This information can be extrapolated to suggest that 3-Bromo-5-(trifluoromethyl)benzenesulfonyl chloride would also exhibit a planar benzene ring with a distinct dihedral angle between the ring and the sulfonyl chloride moiety.

Chemical Reactions Analysis

The reactivity of benzenesulfonyl chloride derivatives is influenced by the presence of substituents on the benzene ring. For example, the anilinium chloride adduct of 4-bromo-N-phenylbenzenesulfonamide displays a hydrogen-bonded ladder motif, indicating the potential for hydrogen bonding in the presence of suitable substituents. The presence of bromo and trifluoromethyl groups in the compound of interest suggests that it could participate in various chemical reactions, such as nucleophilic substitution or as an intermediate in the synthesis of more complex molecules.

Physical and Chemical Properties Analysis

The physical and chemical properties of benzenesulfonyl chloride derivatives are determined by their molecular structure and substituents. The orthorhombic crystal structure of 2,4,5-trichlorobenzenesulfonyl chloride and its density and bond lengths provide a basis for understanding the solid-state properties of similar compounds. The presence of bromo and trifluoromethyl groups in 3-Bromo-5-(trifluoromethyl)benzenesulfonyl chloride would likely influence its boiling point, solubility, and reactivity. Additionally, the interaction of bromo and trifluoromethyl groups with other substituents can lead to various intermolecular interactions, as seen in the X-ray structure determinations of bromo- and bromomethyl-substituted benzenes.

Scientific Research Applications

Use in Palladium-Catalyzed Arylation

3-Bromo-5-(trifluoromethyl)benzenesulfonyl chloride has been explored in palladium-catalyzed arylation processes. For instance, it's used in the Pd-catalyzed desulfitative arylation, which involves coupling with heteroarenes without cleaving the C-Br bonds, leading to regioselective arylations (Skhiri et al., 2015) . This reactivity has been demonstrated with various benzenesulfonyl chlorides, including bromo- and iodobenzenesulfonyl chlorides (Beladhria et al., 2014).

Synthesis of Key Building Blocks

This compound is vital in synthesizing key building blocks for other chemicals. For example, it's used in the synthesis of 2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride, a critical component of penoxsulam (Huang et al., 2019).

Role in Synthesizing Functionalized Arylfurans

3-Bromo-5-(trifluoromethyl)benzenesulfonyl chloride is instrumental in producing functionalized arylfurans. Its use in the palladium-catalyzed desulfitative 5-arylation of furans has been reported, with the reaction tolerating a range of substituents on the benzenesulfonyl derivative (Beladhria et al., 2014).

Application in Conjugate Addition Reactions

The reactivity of 3-Bromo-5-(trifluoromethyl)benzenesulfonyl chloride with enones has been explored, demonstrating its potential in conjugate addition reactions and subsequent transformations (Yuan et al., 2015).

Synthesis of Purine Cyclonucleosides

It has been used in the sulfonylation of bromoadenosine derivatives, leading to the synthesis of purine cyclonucleosides, demonstrating its significance in nucleoside chemistry (Ikehara & Kaneko, 1970).

Direct Arylations with Heteroarenes

Its application extends to direct arylation with heteroarenes, where it acts as a coupling partner, facilitating the synthesis of arylated heteroarenes (Mao et al., 2020).

Photodynamic Therapy Applications

3-Bromo-5-(trifluoromethyl)benzenesulfonyl chloride has been used in the synthesis of new zinc phthalocyanine with potential applications in photodynamic therapy for cancer treatment (Pişkin et al., 2020) .

C-H Bond Functionalization in Organic Synthesis

This compound plays a role in C-H bond functionalization, particularly in the synthesis of arylated fulvenes, demonstrating its versatility in organic synthesis (Brahim et al., 2017).

Safety And Hazards

This compound is classified as a skin corrosive substance (Skin Corr. 1B) and is dangerous. It can cause severe skin burns and eye damage. Therefore, it’s recommended to use personal protective equipment, including a dust mask type N95 (US), eyeshields, and gloves when handling this compound.

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