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CAS 261165-02-0

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(S)-N-BOC-2-Bromophenylalanine

Description:
(S)-N-BOC-2-Bromophenylalanine is a derivative of the amino acid phenylalanine, characterized by the presence of a bromine atom at the 2-position of the phenyl ring and a tert-butyloxycarbonyl (BOC) protecting group on the amino group. This compound is typically used in peptide synthesis and medicinal chemistry due to its ability to serve as a building block for more complex molecules. The BOC group provides stability and protects the amino group during synthetic procedures, allowing for selective reactions. The presence of the bromine atom can facilitate further functionalization or substitution reactions, making it a versatile intermediate. In terms of solubility, it is generally soluble in organic solvents, while its solubility in water may be limited due to the hydrophobic nature of the phenyl group. Additionally, (S)-N-BOC-2-Bromophenylalanine exhibits chirality, with the (S)-enantiomer being biologically relevant in various applications, particularly in the development of pharmaceuticals and biologically active compounds.
Formula:C14H17BrNO4
InChI:InChI=1/C14H18BrNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-6-4-5-7-10(9)15/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/p-1/t11-/m0/s1
SMILES:CC(C)(C)OC(=N[C@@H](Cc1ccccc1Br)C(=O)[O-])O
Synonyms:
  • Boc-L-2-Bromophenylalanine
  • Boc-2-Bromo-L-phenylalanine
  • Boc-Phe(2-Br)-OH
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