3-Bromo-L-phenylalanine

Name: 3-Bromo-L-phenylalanine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 82311-69-1
Cat. No. CS-W008183
Purity≥98%
MDL No.MFCD06659110

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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+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

An item is classified as a dangerous good if our website displays Hazardous Material (HazMat) information for it.

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Structure of 82311-69-1

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General Information

CAS No. 82311-69-1
Cat. No. CS-W008183
Purity ≥98%
MDL No. MFCD06659110
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₀BrNO₂
Molecular Weight 244.09
Synonym(s) None
SMILES BrC1=CC=CC(C[C@H](N)C(O)=O)=C1

Description

3-Bromo-L-phenylalanine integrates a bromine atom at the meta position of the aromatic ring, enabling site-specific bioconjugation and synthetic labeling. This bench-stable amino acid features enhanced reactivity for transition-metal-catalyzed coupling reactions, facilitating efficient incorporation into peptides and protein engineering workflows.

Application

3-Bromo-L-phenylalanine serves as a valuable building block for the synthesis of biologically relevant brominated aromatic compounds and peptidomimetics. Its well-defined stereochemistry and stable side chain facilitate incorporation into peptide sequences and enable subsequent cross-coupling reactions, including palladium-catalyzed transformations. The bromine substituent provides a reliable handle for further functionalization, offering versatility in medicinal chemistry and process development workflows.

Synthesis

Route1
- In-stock
  
  82278-73-7
- ~86%
- In-stock
  
  82311-69-1
References
- UCB PHARMA S.A. Patent: WO2008/47109 A1, 2008 ; Location in patent: Page/Page column 42 ; WO 2008/047109 A1
Route2
- In-stock
  
  14473-91-7
- ~%
- In-stock
  
  82311-69-1
References
- Journal of Organic Chemistry, , 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

Quality Control

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Computational Chemistry Data

TPSA 63.32
LogP 1.4035
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 3

Other Classifications

Bioactive Molecules Peptides

Life Science Amino Acids and their Derivatives Phenylalanine and derivatives

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Key Words

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3-Bromo-L-phenylalanine

CAS No. 82311-69-1

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