Description

(R)-2-Amino-3-(4-bromo-phenyl)-2-methyl-propionic acid (CAS No. 752971-41-8) is a high-purity, chiral non-natural amino acid derivative designed for advanced research and pharmaceutical applications. This compound, with the molecular formula C₁₀H₁₂BrNO₂, features a stereogenic center at the 2-position, making it a valuable building block for asymmetric synthesis and peptidomimetics. The 4-bromophenyl substituent enhances its utility in cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, enabling the introduction of diverse aryl groups. Its IUPAC name, (2R)-2-amino-3-(4-bromophenyl)-2-methylpropanoic acid, reflects its precise structural configuration. Supplied as a white to off-white crystalline powder, it is characterized by HPLC and NMR to ensure ≥95% purity, meeting stringent quality standards for researchers in medicinal chemistry, peptide science, and material science. Store under inert conditions at 2-8°C to maintain stability.

Properties

• CAS Number: 752971-41-8
• Complexity: 214
• IUPAC Name: (2R)-2-amino-3-(4-bromophenyl)-2-methyl-propanoic acid
• InChI: InChI=1S/C10H12BrNO2/c1-10(12,9(13)14)6-7-2-4-8(11)5-3-7/h2-5H,6,12H2,1H3,(H,13,14)/t10-/m1/s1
• InChI Key: PEGRPUVDOKWERK-SNVBAGLBSA-N
• Exact Mass: 257.00514
• Molecular Formula: C10H12BrNO2
• Molecular Weight: 258.11
• SMILES: C[C@@](CC1=CC=C(C=C1)Br)(C(=O)O)N
• Topological: 63.3
• Monoisotopic Mass: 257.00514
• Synonyms: 752971-41-8, H-alpha-Me-D-Phe(4-Br)-OH, (R)-2-Amino-3-(4-bromo-phenyl)-2-methyl-propionic acid, (2R)-2-AMINO-3-(4-BROMOPHENYL)-2-METHYLPROPANOIC ACID, (R)-2-amino-3-(4-bromophenyl)-2-methylpropanoic acid, 4-Bromo-a-methyl-D-phenylalanine, MFCD08752468, SCHEMBL12530276, DTXSID40573940, (R)-alpha-Methyl4-bromophenylalaine, 4-Bromo-alpha-methyl-D-phenylalanine, AKOS027322218, AB48910, DB-257988, CS-0363159, (R)-alpha-Methyl-4-bromophenylalanine (>98%, >94%ee) (H-D-aMePhe(4-Br)-OH)

Application

This compound serves as a key intermediate in the synthesis of chiral ligands, peptidomimetics, and bioactive molecules, particularly in drug discovery targeting GPCRs or enzyme inhibition. Its bromophenyl group facilitates late-stage functionalization via palladium-catalyzed cross-coupling reactions, enabling rapid diversification of lead compounds. Researchers also employ it in the design of constrained peptides to study secondary structure-activity relationships.

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