Fmoc-4-Nitro-L-Phenylalanine (Fmoc-Phe(4-NO2)-OH) is a significant compound within the realm of fine chemicals, particularly valued for its role in advanced organic synthesis and pharmaceutical research. Its chemical structure and properties make it an indispensable building block for creating complex molecules with specific biological activities. This detailed examination will cover its fundamental chemical characteristics, synthesis considerations, and its relevance in various industrial applications.

The compound's identity is firmly established by its Chemical Name: N-Fmoc-4-Nitro-L-Phenylalanine and its unique CAS Number: 95753-55-2. The Molecular Formula, C24H20N2O6, and Molecular Weight of 432.43 g/mol are critical parameters for its handling and use in precise chemical reactions. Physically, it presents as a white to off-white powder with a guaranteed purity of at least 98% (HPLC). For optimal preservation of its chemical integrity, storage at cool temperatures, specifically 2-8°C, in a well-sealed container is advised.

The synthesis of Fmoc-4-Nitro-L-Phenylalanine typically involves the reaction of L-Phenylalanine derivatives with reagents that introduce the Fmoc protecting group and the nitro substitution. Common starting materials and reagents include L-Phenylalanine, N-(9-Fluorenylmethoxycarbonyloxy)succinimide, or 9-Fluorenylmethyl chloroformate, often in the presence of a base like sodium hydroxide and a solvent such as acetonitrile. The detailed synthetic steps, including purification through recrystallization, ensure the high purity required for its downstream applications. The efficiency of these synthesis routes is a key factor in its industrial relevance.

The industrial significance of Fmoc-4-Nitro-L-Phenylalanine is multifaceted. Its primary application is in solid-phase peptide synthesis (SPPS), where it is used to incorporate the modified amino acid residue into growing peptide chains. This modification is critical for creating peptides with enhanced properties, such as improved stability, specific binding capabilities, or spectroscopic tags. As a key intermediate, it is instrumental in the development of VLA-4 integrin antagonists, which are crucial in the research of inflammatory and autoimmune diseases. Moreover, its utility extends to being a precursor for various other complex organic molecules used in medicinal chemistry and materials science.

Sourcing high-quality Fmoc-4-Nitro-L-Phenylalanine is essential for consistent results in research and manufacturing. Suppliers like NINGBO INNO PHARMCHEM CO.,LTD. play a vital role in ensuring the availability of this specialized chemical. The compound's role in advancing fields such as drug discovery and the synthesis of bioactive peptides highlights its importance in the broader chemical industry. Its continued use in cutting-edge research solidifies its position as a valuable component in the chemical synthesis toolkit.