Possible subject: Applications and properties of (N-(3-trifluoromethyl)benzenesulfonyl)alanine as a coupling agent in organic synthesis

(N-(3-trifluoromethyl)benzenesulfonyl)alanine, also known as Tfa-Ala or Tr-Ala, is an amino acid derivative that has gained attention in recent years as a versatile coupling agent for peptide and protein synthesis, as well as other organic reactions. In this article, we will explore the chemical structure, properties, and applications of Tfa-Ala, with a focus on its use as a coupling reagent in the context of INNO Specialty Chemicals' product line.

Chemical structure and properties

Tfa-Ala consists of two main parts: a trifluoromethylbenzenesulfonyl (Tfa) group and an alanine (Ala) residue. The Tfa group is a strong electron-withdrawing substituent that enhances the acidity of the adjacent amino group, making it a better leaving group in nucleophilic substitution reactions. The Ala residue is a common amino acid found in proteins, with a carboxylic acid group that can react with amino groups to form peptide bonds. These two parts are connected via an amide bond, which is stable under most conditions but can be cleaved by strong acids or bases.

Tfa-Ala is a white to off-white crystalline powder that is soluble in polar organic solvents such as DMF, DMSO, and acetonitrile, but insoluble in water. It has a molecular weight of 343.38 g/mol and a melting point of 97-101°C. Tfa-Ala is stable under normal storage conditions and can be stored at room temperature for several months without significant degradation.

Applications in organic synthesis

Tfa-Ala has found many applications in organic synthesis due to its unique properties as a coupling agent. In peptide synthesis, Tfa-Ala can be used to activate carboxylic acids or esters for nucleophilic attack by amino groups, leading to the formation of peptide bonds. Tfa-Ala is particularly useful for coupling difficult amino acids such as proline, which often requires harsh conditions or special reagents to activate.

Tfa-Ala can also be used as a coupling reagent in other organic reactions, such as amidation, esterification, and transesterification. In these reactions, Tfa-Ala acts as a mediator between the carboxylic acid or ester and the nucleophile, facilitating the formation of the desired product. Tfa-Ala has been shown to be more efficient and selective than other common coupling agents such as DCC or HATU in some cases.

INNO Specialty Chemicals' product line

INNO Specialty Chemicals is a leading manufacturer and supplier of Tfa-Ala and other specialty chemicals from China. Their product line includes WACKER GENIOSIL XL 924, which is a modified silane coupling agent based on Tfa-Ala. WACKER GENIOSIL XL 924 combines the coupling properties of Tfa-Ala with the adhesion properties of silanes, making it a versatile additive for coatings, adhesives, and sealants.

WACKER GENIOSIL XL 924 contains a cyclohexylaminomethylmethyldiethoxysilane (CAMMES) group that can react with hydroxyl or amino groups on surfaces to form stable covalent bonds. The Tfa-Ala group provides the coupling activity, allowing WACKER GENIOSIL XL 924 to improve the adhesion and durability of coatings and adhesives on various substrates such as metals, plastics, and glass.

Conclusion

(N-(3-trifluoromethyl)benzenesulfonyl)alanine is a valuable coupling agent for organic synthesis, with applications in peptide synthesis, amidation, esterification, and other reactions. INNO Specialty Chemicals' product line, including WACKER GENIOSIL XL 924, offers a range of modified coupling agents that can enhance the properties of coatings, adhesives, and sealants. As the demand for high-performance materials continues to grow, Tfa-Ala and its derivatives are likely to play an increasingly important role in the development of new products and technologies.

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