3-Bromo-9,10-phenanthrenedione

Name: 3-Bromo-9,10-phenanthrenedione
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 13292-05-2
Cat. No. CS-0155953
Purity≥95%
MDL No.MFCD18072876

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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-Bromo-9,10-phenanthrenedione|CS-0155953

Structure of 13292-05-2

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General Information

CAS No. 13292-05-2
Cat. No. CS-0155953
Purity ≥95%
MDL No. MFCD18072876
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₇BrO₂
Molecular Weight None
Synonym(s) 3-Bromophenanthrene-9,10-dione
SMILES C1=CC=C2C(=C1)C3=C(C=CC(=C3)Br)C(=O)C2=O

Description

3-Bromo-9,10-phenanthrenedione is a brominated quinone derivative featuring a rigid, planar polycyclic aromatic core. This structure enables efficient integration into conjugated systems, offering enhanced electron-withdrawing character and stability under standard bench conditions. The bromine substituent facilitates downstream functionalization via cross-coupling reactions, making it valuable for constructing complex molecular architectures in organic synthesis and materials science.

Application

3-Bromo-9,10-phenanthrenedione serves as a versatile building block in synthetic organic chemistry, enabling regioselective functionalization of polycyclic aromatic frameworks. Its bromine substituent facilitates palladium-catalyzed cross-coupling reactions, while the quinone moiety supports redox-active transformations. The compound exhibits excellent bench stability and is compatible with common protecting group strategies, making it suitable for advanced synthesis workflows involving heterocyclic scaffolds and pharmaceutical intermediates.

Synthesis

Route1
- In-stock
  
  84-11-7
- ~73%
- In-stock
  
  13292-05-2
References
- Song, Yabin; Xu, Wei; Zhu, Daoben Tetrahedron Letters, 2010 , vol. 51, # 37 p. 4894 - 4897
Route2
- In-stock
  
  715-50-4
- ~70%
- In-stock
  
  13292-05-2
References
- MERCK FROSST CANADA LTD. Patent: WO2007/95753 A1, 2007 ; Location in patent: Page/Page column 50 ; WO 2007/095753 A1
Route3
- 53581-38-7
- ~%
- In-stock
  
  13292-05-2
References
- Chemische Berichte, , vol. 39, p. 3118

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS09
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P273-P391-P501

Quality Control

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Computational Chemistry Data

TPSA 34.14
LogP 3.4951
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

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3-Bromo-9,10-phenanthrenedione

CAS No. 13292-05-2

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