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Other Specialized Reagents

BOC-L-4-Chlorophe

Category:

Other Specialized Reagents

CAS NO:

68090-88-0

Standard:

BP,USP,

Price Range:

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Main Sales Markets:

North America,Western Europe,Eastern Europe

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Shanghai Sunwise Chemical Co., Ltd.

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Basic Info

CAS Number

68090-88-0

Pharmacopoeia

BP,USP

Grade

Pharmaceutical Grade

Is Manufacturer

YES

Product Description

Pharmaceutical Raw Materials and Intermediates

AI Product Description

*The following content is generated by AI and is for reference only.

BOC-L-4-Chlorophenylalanine, often identified by the CAS number 15937-28-9, is a valuable protected amino acid derivative widely utilized in organic synthesis and pharmaceutical research. This compound consists of an L-phenylalanine backbone where the para-position of the benzene ring is substituted with a chlorine atom, and the alpha-amino group is protected by a tert-butoxycarbonyl (BOC) moiety. The molecular formula is C₁₃H₁₆ClNO₄, reflecting its complex structure which ensures stability during multi-step synthetic procedures. The primary application of BOC-L-4-chlorophenylalanine lies in peptide chemistry and medicinal chemistry. It serves as a critical building block for the solid-phase or solution-phase synthesis of bioactive peptides and peptidomimetics. The presence of the chlorine substituent significantly alters the electronic and steric properties of the amino acid compared to standard phenylalanine, often enhancing metabolic stability or binding affinity when incorporated into drug candidates. Researchers frequently employ this reagent to construct libraries of compounds for high-throughput screening aimed at discovering new therapeutics for various diseases, including cancer and viral infections. Furthermore, the BOC protecting group is crucial as it remains stable under acidic conditions but can be selectively removed using strong acids like trifluoroacetic acid (TFA) without affecting other sensitive functional groups. This orthogonality allows chemists to manipulate the molecule with precision, facilitating the creation of complex structures with specific stereochemical configurations. Its solubility characteristics make it suitable for use in common organic solvents such as dichloromethane, DMF, and methanol. Due to its chiral nature derived from the L-isomer, it is essential for synthesizing biologically active molecules that require strict stereochemical control. Consequently, BOC-L-4-chlorophenylalanine remains an indispensable reagent in laboratories dedicated to advanced drug discovery and the development of novel agrochemicals, bridging the gap between fundamental chemical research and practical therapeutic applications.