5-Bromo-6-chloropicolinonitrile

Name: 5-Bromo-6-chloropicolinonitrile
Brand: ChemScene
Availability: InStock
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CAS No. 1256823-65-0
Cat. No. CS-W007130
Purity≥95%
MDL No.MFCD18257828

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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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5-Bromo-6-chloropicolinonitrile|CS-W007130

Structure of 1256823-65-0

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General Information

CAS No. 1256823-65-0
Cat. No. CS-W007130
Purity ≥95%
MDL No. MFCD18257828
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₂BrClN₂
Molecular Weight 217.45
Synonym(s) 5-bromo-6-chloropyridine-2-carbonitrile
SMILES N#CC1=NC(Cl)=C(Br)C=C1

Description

5-Bromo-6-chloropicolinonitrile features a highly functionalized pyridine core with orthogonal halogen and nitrile groups, enabling selective coupling in cross-coupling reactions. The electron-deficient ring facilitates nucleophilic substitution, while the steric profile supports controlled reaction pathways. This compound serves as a key intermediate in the synthesis of bioactive heterocycles and advanced pharmaceuticals.

Application

5-Bromo-6-chloropicolinonitrile serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal halogen functionality. The nitrile group provides a handle for selective transformations, while the bromo and chloro substituents offer complementary reactivity for sequential functionalization. Bench-stable and amenable to purification by recrystallization, it facilitates efficient access to substituted pyridine scaffolds relevant to medicinal chemistry and agrochemical development.

Synthesis

Route1
- 7677-24-9
- 1373126-39-6
- ~73%
- In-stock
  
  1256823-65-0
References
- Pettersson, Martin; Johnson, Douglas S.; Subramanyam, Chakrapani; Bales, Kelly R.; Am Ende, Christopher W.; Fish, Benjamin A.; Green, Michael E.; Kauffman, Gregory W.; Lira, Ricardo; Mullins, Patrick B.; Navaratnam, Thayalan; Sakya, Subas M.; Stiff, Cory M.; Tran, Tuan P.; Vetelino, Beth C.; Xie, Longfei; Zhang, Liming; Pustilnik, Leslie R.; Wood, Kathleen M.; O'Donnell, Christopher J. Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 8 p. 2906 - 2911
Route2
- In-stock
  
  52200-48-3
- ~%
- In-stock
  
  1256823-65-0
References
- Pettersson, Martin Youngjin; Johnson, Douglas Scott; Subramanyam, Chakrapani; O'Donnell, Christopher John; Ende, Christopher William Am; Fish, Benjamin Adam; Green, Michael Eric; Mullins, Patrick Bradley; Stiff, Cory Michael; Tran, Tuan Phong; Navaratnam, Thayalan Patent: US2012/252758 A1, 2012 ;

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 36.68
LogP 2.36918
H_Acceptors 2
H_Donors 0
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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5-Bromo-6-chloropicolinonitrile

CAS No. 1256823-65-0

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