(S)-2-amino-3-(7-bromo-1H-indol-3-yl)propanoic acid

Name: (S)-2-amino-3-(7-bromo-1H-indol-3-yl)propanoic acid
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CAS No. 75816-19-2
Cat. No. CS-0466366
Molecule weight283.12
Purity≥98%
MDL No.MFCD09264335

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(S)-2-amino-3-(7-bromo-1H-indol-3-yl)propanoic acid|CS-0466366

Structure of 75816-19-2

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General Information

CAS No. 75816-19-2
Cat. No. CS-0466366
Purity ≥98%
MDL No. MFCD09264335
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₁BrN₂O₂
Molecular Weight 283.12
Synonym(s) L-Trp(7-Br)-OH
SMILES C1=CC2=C(C(=C1)Br)NC=C2C[C@@H](C(=O)O)N

Description

(S)-2-amino-3-(7-bromo-1H-indol-3-yl)propanoic acid is a stereochemically defined tryptophan analog featuring a brominated indole core. This bench-stable derivative integrates a para-brominated indole moiety that enhances electronic properties for bioconjugation and structural probing. The chiral α-amino acid side chain supports incorporation into peptide sequences, enabling site-specific labeling or functionalization in chemical biology applications.

Application

(S)-2-Amino-3-(7-bromo-1H-indol-3-yl)propanoic acid serves as a key chiral building block for indole-based peptidomimetics and bioactive heterocycles. The molecule combines a stable, bench-ready amino acid scaffold with a brominated indole moiety, enabling direct use in Pd-catalyzed cross-coupling reactions and further functionalization. Its defined stereochemistry and high functional group tolerance facilitate efficient synthesis of complex scaffolds relevant to medicinal chemistry programs.

Synthesis

Route1
- In-stock
  
  73-22-3
- ~83%
- In-stock
  
  75816-19-2
References
- Payne, James T.; Andorfer, Mary C.; Lewis, Jared C. Angewandte Chemie - International Edition, 2013 , vol. 52, # 20 p. 5271 - 5274 Angew. Chem., 2013 , vol. 125, # 20 p. 5379 - 5382,4
Route2
- In-stock
  
  51417-51-7
- In-stock
  
  56-45-1
- ~8%
- In-stock
  
  75816-19-2
References
- Kaiser, Markus; Siciliano, Carlo; Assfalg-Machleidt, Irmgard; Groll, Michael; Milbradt, Alexander G.; Moroder, Luis Organic Letters, 2003 , vol. 5, # 19 p. 3435 - 3437
Route3
- 75816-18-1
- ~40%
- In-stock
  
  75816-19-2
- 496929-98-7
References
- Konda-Yamada, Yaeko; Okada, Chiharu; Yoshida, Kiminari; Umeda, Yasuyuki; Arima, Shiho; Sato, Noriko; Kai, Toshitsugu; Takayanagi, Hiroaki; Harigaya, Yoshihiro Tetrahedron, 2002 , vol. 58, # 39 p. 7851 - 7861

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 79.11
LogP 1.8848
H_Acceptors 2
H_Donors 3
Rotatable_Bonds 3

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Tryptophan and derivatives

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-2-amino-3-(7-bromo-1H-indol-3-yl)propanoic acid

CAS No. 75816-19-2

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