5-Bromo-8-nitroisoquinoline

Name: 5-Bromo-8-nitroisoquinoline
Brand: ChemScene
Availability: InStock
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CAS No. 63927-23-1
Cat. No. CS-W008435
Purity≥95%
MDL No.MFCD02091227

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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 63927-23-1

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General Information

CAS No. 63927-23-1
Cat. No. CS-W008435
Purity ≥95%
MDL No. MFCD02091227
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₅BrN₂O₂
Molecular Weight 253.05
Synonym(s) Isoquinoline, 5-bromo-8-nitro-
SMILES BrC1=C2C=CN=CC2=C([N+]([O-])=O)C=C1

Description

5-Bromo-8-nitroisoquinoline features a fused bicyclic scaffold bearing bromine at the 5-position and a nitro group at the 8-position, creating a highly electron-deficient heteroaromatic system. This configuration enables selective cross-coupling reactions and facilitates incorporation into advanced pharmaceutical scaffolds and functional materials. The compound exhibits excellent stability under standard handling conditions.

Application

5-Bromo-8-nitroisoquinoline serves as a versatile building block in medicinal chemistry and heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its bromine substituent. The nitro group at the 8-position provides a handle for selective reduction and further functionalization, supporting downstream derivatization in API development. Its stability under standard reaction conditions and compatibility with diverse coupling protocols make it a practical choice for constructing complex isoquinoline-based scaffolds.

Synthesis

Route1
- In-stock
  
  34784-04-8
- ~98%
- In-stock
  
  63927-23-1
References
- ABBOTT LABORATORIES Patent: WO2004/76424 A1, 2004 ; Location in patent: Page 174-175 ; WO 2004/076424 A1
Route2
- In-stock
  
  119-65-3
- ~45%
- In-stock
  
  63927-23-1
References
- Gomtsyan, Arthur; Bayburt, Erol K.; Schmidt, Robert G.; Guo, Zhu Zheng; Perner, Richard J.; Didomenico, Stanley; Koenig, John R.; Turner, Sean; Jinkerson, Tammie; Drizin, Irene; Hannick, Steven M.; Macri, Bryan S.; McDonald, Heath A.; Honore, Prisca; Wismer, Carol T.; Marsh, Kennan C.; Wetter, Jill; Stewart, Kent D.; Oie, Tetsuro; Jarvis, Michael F.; Surowy, Carol S.; Faltynek, Connie R.; Lee, Chih-Hung Journal of Medicinal Chemistry, 2005 , vol. 48, # 3 p. 744 - 752

Safety Information

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GHS Pictogram :	GHS No : GHS05,GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301-H315-H318
Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 56.03
LogP 2.9055
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Isoquinoline compounds

Key Words

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5-Bromo-8-nitroisoquinoline

CAS No. 63927-23-1

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