Boc-Phe(3-Br)-OH

Name: Boc-Phe(3-Br)-OH
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 82278-73-7
Cat. No. CS-W022606
Purity≥97%
MDL No.MFCD01317710

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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+

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Structure of 82278-73-7

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General Information

CAS No. 82278-73-7
Cat. No. CS-W022606
Purity ≥97%
MDL No. MFCD01317710
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₈BrNO₄
Molecular Weight 344.20
Synonym(s) None
SMILES CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC(Br)=C1)C(O)=O

Description

Boc-Phe(3-Br)-OH features a para-brominated phenylalanine residue with a robust Boc protecting group, enabling stable incorporation into peptide chains. This electron-deficient aryl moiety enhances coupling efficiency and facilitates downstream functionalization in synthetic peptide workflows.

Application

Boc-Phe(3-Br)-OH serves as a versatile building block for the synthesis of brominated phenylalanine derivatives, enabling efficient incorporation of a meta-bromophenyl side chain into peptide scaffolds. The Boc group provides stable protection of the amine, while the 3-bromo substituent offers a reactive handle for palladium-catalyzed cross-coupling reactions. Its bench-stable nature and compatibility with standard peptide coupling protocols make it ideal for medicinal chemistry campaigns requiring halogenated aromatic motifs.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  82311-69-1
- ~95%
- In-stock
  
  82278-73-7
References
- ACS Medicinal Chemistry Letters, , vol. 3, # 3 p. 203 - 206
Route2
- 880347-42-2
- In-stock
  
  24424-99-5
- ~17%
- In-stock
  
  82278-73-7
References
- US2006/69286 A1, ; Page/Page column 20 ; US 20060069286 A1

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 75.63
LogP 2.9695
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Bioactive Molecules Peptides

Life Science Amino Acids and their Derivatives Phenylalanine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Key Words

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Boc-Phe(3-Br)-OH

CAS No. 82278-73-7

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