6-Bromoquinazolin-2-amine

Name: 6-Bromoquinazolin-2-amine
Brand: ChemScene
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CAS No. 190273-89-3
Cat. No. CS-0001994
Purity≥97%
MDL No.MFCD04114089

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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 190273-89-3

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General Information

CAS No. 190273-89-3
Cat. No. CS-0001994
Purity ≥97%
MDL No. MFCD04114089
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₆BrN₃
Molecular Weight 224.06
Synonym(s) 6-Bromoquinazolin-2-ylamine
SMILES NC1=NC=C2C=C(Br)C=CC2=N1

Description

6-Bromoquinazolin-2-amine is a bench-stable heterocyclic building block featuring a bromine atom at the 6-position and an amino group at the 2-position. This combination enables direct functionalization in cross-coupling reactions, facilitating rapid access to diverse quinazoline-based scaffolds for medicinal chemistry and materials science applications.

Application

6-Bromoquinazolin-2-amine serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the C6 position via palladium-catalyzed cross-coupling reactions. Its bromine substituent exhibits excellent compatibility with Suzuki, Stille, and Negishi couplings, facilitating rapid diversification of quinazoline scaffolds. The molecule demonstrates bench stability, ease of purification, and tolerance to common functional groups, making it well-suited for iterative synthesis of kinase inhibitors and other bioactive heterocycles.

Synthesis

Route1
- In-stock
  
  593-85-1
- In-stock
  
  93777-26-5
- ~48%
- In-stock
  
  190273-89-3
References
- Hu, Essa; Tasker, Andrew; White, Ryan D.; Kunz, Roxanne K.; Human, Jason; Chen, Ning; Buerli, Roland; Hungate, Randall; Novak, Perry; Itano, Andrea; Zhang, Xuxia; Yu, Violeta; Nguyen, Yen; Tudor, Yanyan; Plant, Matthew; Flynn, Shaun; Xu, Yang; Meagher, Kristin L.; Whittington, Douglas A.; Ng, Gordon Y. Journal of Medicinal Chemistry, 2008 , vol. 51, # 11 p. 3065 - 3068
Route2
- 124-46-9
- In-stock
  
  93777-26-5
- ~%
- In-stock
  
  190273-89-3
References
- US2006/35897 A1, ; Page/Page column 32 ;

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 51.8
LogP 1.9745
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Quinazoline compounds

Key Words

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6-Bromoquinazolin-2-amine

CAS No. 190273-89-3

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