3,6-Dibromophenanthrene-9,10-dione

Name: 3,6-Dibromophenanthrene-9,10-dione
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 53348-05-3
Cat. No. CS-0080728
Purity≥95%
MDL No.MFCD00451676

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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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3,6-Dibromophenanthrene-9,10-dione|CS-0080728

Structure of 53348-05-3

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General Information

CAS No. 53348-05-3
Cat. No. CS-0080728
Purity ≥95%
MDL No. MFCD00451676
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₆Br₂O₂
Molecular Weight 366.00
Synonym(s) 6-Dibromo-phenanthrenequinone
SMILES O=C1C2=C(C=C(Br)C=C2)C3=CC(Br)=CC=C3C1=O

Description

3,6-Dibromophenanthrene-9,10-dione features two bromine substituents at the 3 and 6 positions of a phenanthrene core, flanking a quinone moiety. This electron-deficient architecture enables efficient coupling in transition metal-catalyzed reactions, offering high reactivity in cross-coupling and functionalization processes. The molecule exhibits excellent stability under standard bench conditions and integrates readily into complex molecular frameworks.

Application

3,6-Dibromophenanthrene-9,10-dione serves as a versatile building block for the synthesis of polycyclic aromatic systems and functionalized heterocycles. The dibromo substitution pattern enables selective cross-coupling reactions, while the quinone functionality supports redox-active transformations and Diels-Alder cycloadditions. Its bench-stable crystalline form facilitates handling and purification, making it suitable for iterative synthetic sequences in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  84-11-7
- ~97%
- In-stock
  
  53348-05-3
References
- Brunner, Klemens; Van Dijken, Addy; Boerner, Herbert; Bastiaansen, Jolanda J. A. M.; Kiggen, Nicole M. M.; Langeveld, Bea M. W. Journal of the American Chemical Society, 2004 , vol. 126, # 19 p. 6035 - 6042
Route2
- In-stock
  
  85-01-8
- ~%
- In-stock
  
  53348-05-3
References
- Arkivoc, , vol. 2011, # 9 p. 15 - 37

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 34.14
LogP 4.2576
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Material Science Material Building Blocks Small Molecule Semiconductor Building Blocks Phenanthrenes

Key Words

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3,6-Dibromophenanthrene-9,10-dione

CAS No. 53348-05-3

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