5-Bromobenzo[de]isochromene-1,3-dione

Name: 5-Bromobenzo[de]isochromene-1,3-dione
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 24050-49-5
Cat. No. CS-W012311
Purity≥96%
MDL No.MFCD00228162

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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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5-Bromobenzo[de]isochromene-1,3-dione|CS-W012311

Structure of 24050-49-5

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General Information

CAS No. 24050-49-5
Cat. No. CS-W012311
Purity ≥96%
MDL No. MFCD00228162
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₅BrO₃
Molecular Weight 277.07
Synonym(s) 7-bromo-3-oxatricyclo[7.3.1.0,13]trideca-1(13),5,7,9,11-pentaene-2,4-dione
SMILES BrC1=CC2=CC=CC3=C2C(=C1)C(=O)OC3=O

Description

5-Bromobenzo[de]isochromene-1,3-dione features a fused polycyclic core with a bromine substituent at the 5-position, enabling direct functionalization in transition-metal-catalyzed coupling reactions. The quinone moiety provides redox activity and enhances reactivity in cycloadditions. This scaffold exhibits excellent stability under standard bench conditions and serves as a high-value building block for complex molecular architectures in medicinal chemistry and materials science.

Application

5-Bromobenzo[de]isochromene-1,3-dione serves as a versatile brominated heterocyclic building block for transition-metal-catalyzed coupling reactions. Its electron-deficient aromatic system and strategically positioned bromine facilitate efficient cross-coupling with boronic acids and organostannanes, enabling rapid access to complex polycyclic scaffolds. The molecule exhibits good bench stability and compatibility with standard purification methods, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

Route1
- 81-84-5
- ~98%
- In-stock
  
  24050-49-5
References
- Pinto-Bazurco Mendieta, Mariano A.E.; Negri, Matthias; Jagusch, Carsten; Hille, Ulrike E.; Mueller-Vieira, Ursula; Schmidt, Dirk; Hansen, Klaus; Hartmann, Rolf W. Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 1 p. 267 - 273
Route2
- 81-84-5
- ~%
- In-stock
  
  24050-49-5
- 1190615-88-3
References
- Kuethe, Jeffrey T.; Childers, Karla G.; Humphrey, Guy R.; Journet, Michel; Peng, Zhihui Organic Process Research and Development, 2008 , vol. 12, # 6 p. 1201 - 1208

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 43.37
LogP 2.9129
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Other aromatic heterocycles compounds

Key Words

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5-Bromobenzo[de]isochromene-1,3-dione

CAS No. 24050-49-5

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