2-Bromo-5-nitropyridine

Name: 2-Bromo-5-nitropyridine
Brand: ChemScene
Availability: InStock
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CAS No. 4487-59-6
Cat. No. CS-W007858
Purity≥98%
MDL No.MFCD00006222

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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 4487-59-6

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General Information

CAS No. 4487-59-6
Cat. No. CS-W007858
Purity ≥98%
MDL No. MFCD00006222
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₃BrN₂O₂
Molecular Weight 202.99
Synonym(s) None
SMILES BrC1=NC=C([N+]([O-])=O)C=C1

Description

2-Bromo-5-nitropyridine features a bromine atom at the 2-position and a nitro group at the 5-position on the pyridine ring, creating a highly functionalized heterocycle. This electronic asymmetry enables selective cross-coupling reactions and facilitates incorporation into complex molecular architectures. The molecule exhibits enhanced reactivity in palladium-catalyzed transformations due to the electron-withdrawing nature of both substituents. Its bench-stable solid form ensures reliable handling under standard laboratory conditions.

Application

2-Bromo-5-nitropyridine serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its compatible bromine and nitro functionalities. The nitro group facilitates subsequent reduction and functionalization, while the pyridine core provides orthogonal reactivity for medicinal chemistry applications. Bench-stable and readily purified by recrystallization, it functions efficiently in standard coupling protocols and scaffold elaboration workflows.

Synthesis

Route1
- In-stock
  
  5418-51-9
- ~%
- In-stock
  
  4487-59-6
References
- Binz; v. Schickh Chemische Berichte, 1935 , vol. 68, p. 315,321
Route2
- In-stock
  
  5418-51-9
- ~68%
- In-stock
  
  4487-59-6
- In-stock
  
  15862-36-9
References
- Ager, David J.; Erickson, Robert A.; Froen, Diane E.; Prakash, Indra; Zhi, Ben Organic Process Research and Development, 2004 , vol. 8, # 1 p. 62 - 71
Route3
- In-stock
  
  4214-76-0
- ~29%
- In-stock
  
  4487-59-6
References
- Ongarora, Dennis S.B.; Gut, Jiri; Rosenthal, Philip J.; Masimirembwa, Collen M.; Chibale, Kelly Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 15 p. 5046 - 5050

Safety Information

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GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 56.03
LogP 1.7523
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Bioactive Molecules Dye and Bio-assay Reagents

Building Blocks Functional Group Nitro compounds

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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2-Bromo-5-nitropyridine

CAS No. 4487-59-6

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