Description

(S)-alpha-Methyl-4-bromophenylalanine (CAS No. 747397-27-9) is a high-purity, chiral amino acid derivative with the molecular formula C₁₀H₁₂BrNO₂. This compound, also known by its IUPAC name (2S)-2-amino-3-(4-bromophenyl)-2-methylpropanoic acid, is a valuable building block for pharmaceutical research and peptide synthesis. The bromine substitution at the para position of the phenyl ring enhances its reactivity, making it ideal for cross-coupling reactions and other synthetic modifications. With a defined stereocenter at the alpha-carbon, this product is rigorously characterized by HPLC, NMR, and mass spectrometry to ensure >98% chemical and enantiomeric purity. Suitable for use in medicinal chemistry, asymmetric synthesis, and biochemical studies, it is supplied as a white to off-white crystalline powder under inert packaging to maintain stability.

Properties

• CAS Number: 747397-27-9
• Complexity: 214
• IUPAC Name: (2S)-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-/m0/s1
• InChI Key: PEGRPUVDOKWERK-JTQLQIEISA-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: 747397-27-9, H-alpha-Me-L-Phe(4-Br)-OH, (S)-ALPHA-METHYL-4-BROMOPHENYLALANINE, (S)-alpha-Mmethyl-4-bromophenylalanine, (2S)-2-AMINO-3-(4-BROMOPHENYL)-2-METHYLPROPANOIC ACID, 4-Bromo-a-methyl-L-phenylalanine, (S)-2-Amino-3-(4-bromo-phenyl)-2-methyl-propionic acid, (S)-alpha-Methyl-4-bromophenylalanine (>98%, >98%ee), DTXSID50659663, (S)-alpha-Methyl4-bromophenylalaine, 4-Bromo-alpha-methyl-L-phenylalanine, AKOS030213023, L-Phenylalanine, 4-bromo-|A-methyl-, AB48912, AT40645, CS-0455443, (S)-2-amino-3-(4-bromophenyl)-2-methylpropanoic acid, S-747397-27-9

Application

(S)-alpha-Methyl-4-bromophenylalanine is widely used as a key intermediate in the synthesis of chiral drugs and bioactive peptides. Its brominated aromatic ring facilitates Suzuki-Miyaura and other palladium-catalyzed coupling reactions for structural diversification. Researchers employ this compound in the development of enzyme inhibitors and receptor modulators due to its sterically constrained alpha-methyl group. It also serves as a precursor for labeled analogs in metabolic and pharmacokinetic studies.

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