2-Amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid

Name: 2-Amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid
Brand: ChemScene
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CAS No. 54788-30-6
Cat. No. CS-0157103
Purity≥96%
MDL No.MFCD09842061

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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2-Amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid|CS-0157103

Structure of 54788-30-6

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General Information

CAS No. 54788-30-6
Cat. No. CS-0157103
Purity ≥96%
MDL No. MFCD09842061
Storage RT, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₀BrNO₃
Molecular Weight 260.08
Synonym(s) 3-Bromotyrosine
SMILES C1=CC(=C(C=C1CC(C(=O)O)N)Br)O

Description

This amino acid derivative features a brominated hydroxyphenyl moiety integrated at the β-position, enhancing its utility in bioconjugation and peptide-based drug discovery. The pendant phenolic hydroxyl group enables further derivatization, while the α-amino and carboxylic acid functionalities support robust coupling chemistry under standard conditions.

Application

2-Amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid serves as a versatile building block for bioactive heterocycles and peptide-like scaffolds. Its ortho-hydroxyl and bromo substituents enable efficient downstream functionalization via Suzuki-Miyaura coupling, electrophilic substitution, or metal-catalyzed cross-coupling. The molecule exhibits bench stability, tolerates common protecting group manipulations, and facilitates the synthesis of pharmaceutically relevant arylalanine derivatives through standard peptide coupling protocols.

Synthesis

Route1
- In-stock
  
  556-02-5
- ~%
- In-stock
  
  54788-30-6
References
- Rosenmund; Kuhnhenn; Lesch Chemische Berichte, 1923 , vol. 56, p. 2043 Full Text Show Details Zeynek Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1925 , vol. 144, p. 250
Route2
- 98778-82-6
- ~%
- In-stock
  
  54788-30-6
References
- Johnson; Bengis Journal of the American Chemical Society, 1912 , vol. 34, p. 1056

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 83.55
LogP 1.1091
H_Acceptors 3
H_Donors 3
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Phenol

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Key Words

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2-Amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid

CAS No. 54788-30-6

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