Description

(S)-2-Amino-3-(2-bromophenyl)-2-methylpropanoic acid (CAS No. 1212180-27-2) is a high-purity, chiral amino acid derivative designed for advanced research and pharmaceutical applications. With the molecular formula C₁₀H₁₂BrNO₂, this compound features a stereogenic center at the 2-position, making it a valuable building block for asymmetric synthesis and medicinal chemistry studies. The 2-bromophenyl substitution enhances its utility in cross-coupling reactions, while the methyl group at the alpha position offers steric control for selective transformations. This product is rigorously characterized by HPLC, NMR, and mass spectrometry to ensure ≥95% chemical and enantiomeric purity. Supplied as a crystalline solid with precise lot-specific COA data, it is ideal for drug discovery, peptidomimetics, and organocatalyst development. Store under inert conditions at -20°C for long-term stability.

Properties

• CAS Number: 1212180-27-2
• Complexity: 222
• IUPAC Name: (2S)-2-amino-3-(2-bromophenyl)-2-methyl-propanoic acid
• InChI: InChI=1S/C10H12BrNO2/c1-10(12,9(13)14)6-7-4-2-3-5-8(7)11/h2-5H,6,12H2,1H3,(H,13,14)/t10-/m0/s1
• InChI Key: CEQZLKYRAINNIW-JTQLQIEISA-N
• Exact Mass: 257.00514
• Molecular Formula: C10H12BrNO2
• Molecular Weight: 258.11
• SMILES: C[C@](CC1=CC=CC=C1Br)(C(=O)O)N
• Topological: 63.3
• Monoisotopic Mass: 257.00514
• Synonyms: 1212180-27-2, (S)-2-Amino-3-(2-bromophenyl)-2-methylpropanoic acid, (2S)-2-amino-3-(2-bromophenyl)-2-methylpropanoic acid, alpha-Me-Phe(2-Br)-OH.H2O, (S)-N-Methyl 2-bromophenylalaine, (S)-N-Methyl2-bromophenylalaine, AKOS025290695, AS-60278, DS-019193, CS-0442494

Application

This brominated phenylalanine derivative is primarily employed in peptide modification to introduce steric hindrance and halogenated aromatic motifs. Researchers utilize it as a chiral precursor for organocatalysts in asymmetric C-C bond formations. The bromine atom facilitates palladium-catalyzed cross-coupling reactions (e.g., Suzuki-Miyaura) in pharmaceutical intermediate synthesis. Its constrained geometry makes it valuable for studying enzyme-substrate interactions in structural biology.

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