NINGBO INNO PHARMCHEM CO.,LTD. is pleased to provide an overview of N-(tert-Butoxycarbonyl)-p-toluenesulfonamide (CAS: 18303-04-3), a significant compound in the landscape of organic chemistry. This article will cover its fundamental properties, typical synthesis approaches, and its pivotal applications in various synthetic methodologies.

N-(tert-Butoxycarbonyl)-p-toluenesulfonamide is an organic molecule characterized by its chemical formula C12H17NO4S and a molecular weight of 271.33. It typically presents as a white to off-white crystalline powder, with a melting point in the range of 121-123 °C. The compound exhibits good solubility in common organic solvents like chloroform, which is advantageous for its use in reactions. Its stability under standard laboratory conditions (sealed, dry, room temperature) further adds to its utility.

The synthesis of N-(tert-Butoxycarbonyl)-p-toluenesulfonamide generally involves the N-protection of p-toluenesulfonamide. This protection step typically utilizes di-tert-butyl dicarbonate (Boc anhydride) under basic conditions. The resulting compound serves as a versatile intermediate, facilitating further chemical transformations. The availability of efficient synthesis routes for protected amines is critical for the progression of complex organic synthesis projects.

The primary applications of N-(tert-Butoxycarbonyl)-p-toluenesulfonamide are found in its participation in significant named reactions. It is a well-established precursor for the Pauson-Khand reaction, a powerful method for synthesizing cyclic structures, particularly cyclopentenones. These cyclic systems are foundational in the synthesis of many natural products and bioactive molecules. Moreover, its role in the Mitsunobu reaction allows for the efficient conversion of alcohols into sulfonyl-protected amines, a key transformation in creating complex nitrogen-containing organic molecules.

As a reliable organic chemistry intermediate, N-(tert-Butoxycarbonyl)-p-toluenesulfonamide is a valuable asset for researchers in academic institutions and the chemical industry. NINGBO INNO PHARMCHEM CO.,LTD. is committed to providing this essential compound with high purity and consistent quality, supporting advancements in areas such as drug discovery and materials science. The strategic importance of understanding sulfonamide chemistry cannot be overstated in the design of efficient synthetic pathways.

In summary, N-(tert-Butoxycarbonyl)-p-toluenesulfonamide is a compound of considerable utility, offering broad applicability in sophisticated organic synthesis. Its participation in the Pauson-Khand and Mitsunobu reactions highlights its value as a key intermediate for creating complex molecular architectures.