5-Bromo-1H-benzo[d][1,3]oxazine-2,4-dione

Name: 5-Bromo-1H-benzo[d][1,3]oxazine-2,4-dione
Brand: ChemScene
Availability: InStock
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CAS No. 77603-45-3
Cat. No. CS-0041521
Molecule weight242.03
Purity≥95%
MDL No.MFCD15526667

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Type	HazMat Fee
Excepted Quantity	$0.00
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5-Bromo-1H-benzo[d][1,3]oxazine-2,4-dione|CS-0041521

Structure of 77603-45-3

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General Information

CAS No. 77603-45-3
Cat. No. CS-0041521
Purity ≥95%
MDL No. MFCD15526667
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₄BrNO₃
Molecular Weight 242.03
Synonym(s) Isatoicanhydride, 6-bromo-
SMILES O=C(NC1=CC=CC(Br)=C12)OC2=O

Description

5-Bromo-1H-benzo[d][1,3]oxazine-2,4-dione features a brominated oxazine core with dual carbonyl groups, enabling direct incorporation into heterocyclic scaffolds. The electron-deficient ring system facilitates nucleophilic substitution and transition-metal-catalyzed coupling reactions. Bench-stable and moisture-tolerant, this reagent streamlines access to functionalized benzoxazine derivatives in medicinal chemistry and materials science applications.

Application

5-Bromo-1H-benzo[d][1,3]oxazine-2,4-dione serves as a versatile heterocyclic building block for medicinal chemistry and materials synthesis. Its bromine substituent enables palladium-catalyzed cross-coupling reactions, while the electron-deficient oxazine core facilitates nucleophilic substitution and cycloaddition processes. The compound exhibits good bench stability and is compatible with standard purification techniques, making it well-suited for iterative synthetic workflows in API development.

Synthesis

Route1
- 75-44-5
- In-stock
  
  20776-48-1
- ~91%
- In-stock
  
  77603-45-3
References
- Australian Journal of Chemistry, , vol. 52, # 11 p. 1061 - 1069
Route2
- In-stock
  
  98600-34-1
- ~54%
- In-stock
  
  77603-45-3
References
- Organic and Biomolecular Chemistry, , vol. 11, # 43 p. 7455 - 7457
Route3
- In-stock
  
  20780-72-7
- ~%
- In-stock
  
  77603-45-3
References
- US5599814 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 63.07
LogP 1.2438
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Other aromatic heterocycles compounds

Key Words

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5-Bromo-1H-benzo[d][1,3]oxazine-2,4-dione

CAS No. 77603-45-3

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