Trimethylsulfoxonium bromide CAS 25596-24-1

What is Trimethylsulfoxonium bromide CAS 25596-24-1 ?

Trimethylsulfoxonium bromide CAS 25596-24-1 is a kind of organic synthesis reagent with high chemical reactivity. It is a white solid powder under normal temperature and pressure. Soluble in water, methanol, ethanol and other polar solvents. It is relatively stable at room temperature and pressure, but may decompose or react at high temperatures, humidity or in contact with strong oxidants.

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Ứng dụng

Trimethyl sulfoxide bromide is widely used in organic synthesis, mainly including the following aspects:

Bromination reaction

Bromination of alcohols: It converts alcohols to bromo-hydrocarbons, such as n-butanol to 1-bromo-butane. The reaction condition is mild and the selectivity is good. Compared with other bromine reagents, the side reaction can be reduced and the purity and yield of the product can be improved.

Bromination of phenols: In the bromination reaction of phenolic compounds, trimethyl sulfoxide bromide can selectively introduce bromine atoms in the ortho-position or para-position of the phenol hydroxyl group. Taking p-cresol as an example, the o-bromo-p-cresol can be obtained by introducing bromine atoms in its orthosite, which is of great significance in drug synthesis and the preparation of fine chemical products.

Oxidation reaction

Oxidation of thioether to sulfoxide: can efficiently oxidize thioether to sulfoxide, such as the oxidation of dimethyl sulfide to dimethyl sulfoxide. The reaction has high atomic economy and relatively mild reaction conditions, which is one of the important methods for synthesizing sulfoxides.

Oxidation of aldehydes: aldehydes can be oxidized to corresponding carboxylic acids. For example, benzaldehyde can be oxidized to benzoic acid under the action of trimethyl sulfoxide. This oxidation method is easy to operate, the product purity is high, and it is often used to construct carboxylic acid compounds in organic synthesis.

Other applications

Participation in the synthesis of heterocyclic compounds: In the synthesis of some heterocyclic compounds, trimethyl sulfoxide bromide can be used as a key reagent to participate in the reaction. For example, in the synthesis of some heterocyclic compounds containing sulfur or oxygen, it can promote the cyclization reaction by providing bromine atoms or participating in the oxidation process, which provides an effective method for the synthesis of heterocyclic compounds.

As a mild halogenation reagent: In addition to bromination reactions, in some specific cases, trimethyl sulfoxide bromide can also be used as a mild halogenation reagent to participate in the introduction of other halogen atoms. For example, in some reaction systems, it can exchange reactions with other halide ions, introducing chlorine atoms or iodine atoms into organic compounds, enriching the means of halogenation reaction in organic synthesis.

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