4-Bromoisoquinolin-1-amine

Name: 4-Bromoisoquinolin-1-amine
Brand: ChemScene
Availability: InStock
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CAS No. 55270-27-4
Cat. No. CS-W022122
Purity≥96%
MDL No.MFCD05155261

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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+
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Structure of 55270-27-4

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General Information

CAS No. 55270-27-4
Cat. No. CS-W022122
Purity ≥96%
MDL No. MFCD05155261
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₇BrN₂
Molecular Weight 223.07
Synonym(s) 4-Bromoisoquinolin-1-ylamine
SMILES NC1=NC=C(Br)C2=C1C=CC=C2

Description

4-Bromoisoquinolin-1-amine is a brominated isoquinoline derivative featuring a primary amine at the 1-position. This scaffold integrates a reactive halogen and a basic nitrogen, enabling direct functionalization in cross-coupling reactions and facilitating conjugation to biomolecules. The electron-deficient aromatic core supports transition metal catalysis, while the amine group enhances solubility and provides a handle for derivatization. This compound serves as a key building block in medicinal chemistry and materials science.

Application

4-Bromoisoquinolin-1-amine serves as a versatile building block in medicinal chemistry, enabling direct incorporation into heterocyclic scaffolds via Pd-catalyzed cross-coupling reactions. Its bromine and primary amine functionalities offer orthogonal reactivity for sequential functionalization, while the isoquinoline core provides structural rigidity and π-stacking potential. Bench-stable and readily purified by recrystallization, it facilitates efficient synthesis of kinase inhibitors and CNS-targeted compounds.

Synthesis

Route1
- In-stock
  
  1532-84-9
- ~88%
- In-stock
  
  55270-27-4
References
- Huang; Haddadin; Olmstead; Kurth Journal of Organic Chemistry, 2001 , vol. 66, # 4 p. 1310 - 1315

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 38.91
LogP 2.5795
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Isoquinoline compounds

Key Words

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4-Bromoisoquinolin-1-amine

CAS No. 55270-27-4

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