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

  • CAS No. 267225-27-4

  • Cat. No. CS-0112881
  • Purity≥97%
  • MDL No.MFCD03092959

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

(R)-2-Amino-3-(2-bromophenyl)propanoic acid|CS-0112881

Structure of 267225-27-4

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General Information

  • CAS No. 267225-27-4
  • Cat. No. CS-0112881
  • Purity ≥97%
  • MDL No. MFCD03092959
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₀BrNO₂
  • Molecular Weight 244.09
  • Synonym(s) H-D-Phe(2-Br)-OH
  • SMILES N[C@H](CC1=CC=CC=C1Br)C(O)=O

Description

(R)-2-Amino-3-(2-bromophenyl)propanoic acid is a chiral building block featuring a sterically hindered β-branched structure and a para-brominated aromatic ring. This configuration enables direct incorporation into peptide sequences with defined stereochemistry, offering enhanced metabolic stability and selectivity in bioactive molecule synthesis under standard bench conditions.

Application

(R)-2-Amino-3-(2-bromophenyl)propanoic acid serves as a valuable chiral building block for the synthesis of biologically active compounds, particularly in medicinal chemistry. Its well-defined stereochemistry and compatibility with standard peptide coupling protocols enable efficient incorporation into peptidomimetics and pharmaceutically relevant scaffolds. The bromophenyl group facilitates downstream functionalization via palladium-catalyzed cross-coupling reactions, enhancing structural diversity in drug discovery campaigns. Bench-stable and readily purified by recrystallization, it supports robust scale-up in process development.

Synthesis

  • Route1

    References

    • Tetrahedron Letters, , vol. 49, # 45 p. 6468 - 6470

Safety Information

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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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