2-Amino-5-bromonicotinonitrile

Name: 2-Amino-5-bromonicotinonitrile
Brand: ChemScene
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CAS No. 709652-82-4
Cat. No. CS-W015659
Purity≥95%
MDL No.MFCD08688591

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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2-Amino-5-bromonicotinonitrile|CS-W015659

Structure of 709652-82-4

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General Information

CAS No. 709652-82-4
Cat. No. CS-W015659
Purity ≥95%
MDL No. MFCD08688591
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄BrN₃
Molecular Weight 198.02
Synonym(s) 5-Bromo-3-cyanopyridin-2-amine
SMILES N#CC1=C(N)N=CC(Br)=C1

Description

2-Amino-5-bromonicotinonitrile features a brominated pyridine core with complementary amino and nitrile functionalities, enabling direct incorporation into diverse heterocyclic scaffolds. The electron-deficient ring facilitates cross-coupling reactions, while the amine group offers a handle for derivatization under mild conditions. This compound serves as a key intermediate in medicinal chemistry campaigns targeting kinase inhibitors and CNS-active molecules.

Application

2-Amino-5-bromonicotinonitrile serves as a versatile building block in medicinal chemistry, enabling efficient access to substituted pyridine scaffolds via standard coupling and cyclization reactions. Its bromo and nitrile functionalities offer orthogonal reactivity for palladium-catalyzed cross-couplings and hydrolysis to carboxylic acids, respectively. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis campaigns in API development.

Synthesis

Route1
- In-stock
  
  24517-64-4
- ~99%
- In-stock
  
  709652-82-4
References
- VERTEX PHARMACEUTICALS INCORPORATED Patent: WO2007/59219 A1, 2007 ; Location in patent: Page/Page column 54 ; WO 2007/059219 A1

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05,GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301-H315-H318-H335
Precautionary Statements : P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P363-P405-P501

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Computational Chemistry Data

TPSA 62.7
LogP 1.29798
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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2-Amino-5-bromonicotinonitrile

CAS No. 709652-82-4

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