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CS-W001157 4
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(S)-2-Amino-3-(2-bromophenyl)propanoic acid

  • CAS No. 42538-40-9

  • Cat. No. CS-0059190
  • Purity≥97%
  • MDL No.MFCD03092958

*For research and further manufacturing use only, not for direct human use.

(S)-2-Amino-3-(2-bromophenyl)propanoic acid|CS-0059190

Structure of 42538-40-9

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General Information

  • CAS No. 42538-40-9
  • Cat. No. CS-0059190
  • Purity ≥97%
  • MDL No. MFCD03092958
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₀BrNO₂
  • Molecular Weight 244.09
  • Synonym(s) ortho-broMo-L-phenylalanine; 2-Bromo-L-phenylalanine
  • SMILES N[C@@H](CC1=CC=CC=C1Br)C(O)=O

Description

(S)-2-Amino-3-(2-bromophenyl)propanoic acid is a chiral building block featuring a brominated aromatic ring and a stereogenic center. This configuration enables selective incorporation into bioactive molecules, particularly in peptide synthesis and pharmaceutical intermediates. The molecule exhibits enhanced stability under standard handling conditions, facilitating reliable use in complex reaction sequences.

Application

(S)-2-Amino-3-(2-bromophenyl)propanoic acid serves as a valuable chiral building block for the synthesis of biologically active compounds and peptide mimetics. Its well-defined stereochemistry and compatibility with standard coupling reactions enable reliable incorporation into complex architectures. The pendant bromophenyl group facilitates further functionalization via palladium-catalyzed cross-coupling, offering versatility in medicinal chemistry and materials science applications. Bench-stable and readily purified, it supports scalable synthesis workflows.

Synthesis

  • Route1

    References

    • Zhang, Zizhang Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 4 p. 1129 - 1131
  • Route2

    References

    • Yokoyama, Yuusaku; Yamaguchi, Tomotsugu; Sato, Masanori; Kobayashi, Eri; Murakami, Yasuoki; Okuno, Hiroaki Chemical and Pharmaceutical Bulletin, 2006 , vol. 54, # 12 p. 1715 - 1719
  • Route3
    • (E)-3-(2-Bromophenyl)acrylic acid|CS-W014204
      7345-79-1
    • ~%
    • In-stock
      (S)-2-Amino-3-(2-bromophenyl)propanoic acid|CS-0059190
      42538-40-9

    References

    • Szymanski, Wiktor; Wu, Bian; Weiner, Barbara; De Wildeman, Stefaan; Feringa, Ben L.; Janssen, Dick B. Journal of Organic Chemistry, 2009 , vol. 74, # 23 p. 9152 - 9157

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   63.32
  • LogP   1.4035
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   3

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