2,6-Dibromo-3-nitropyridine

Name: 2,6-Dibromo-3-nitropyridine
Brand: ChemScene
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CAS No. 55304-80-8
Cat. No. CS-W000354
Purity≥95%
MDL No.MFCD00233995

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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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General Information

CAS No. 55304-80-8
Cat. No. CS-W000354
Purity ≥95%
MDL No. MFCD00233995
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₂Br₂N₂O₂
Molecular Weight 281.89
Synonym(s) None
SMILES O=[N+](C1=CC=C(Br)N=C1Br)[O-]

Description

2,6-Dibromo-3-nitropyridine features a pyridine core bearing two bromine atoms at the 2- and 6-positions and a nitro group at the 3-position, creating a highly electron-deficient heterocyclic scaffold. This arrangement enables selective coupling reactions in late-stage functionalization, particularly in cross-coupling and metal-mediated transformations. The molecule exhibits excellent stability under standard bench conditions and offers predictable regiochemistry due to the electronic bias imposed by the nitro and halogen substituents.

Application

2,6-Dibromo-3-nitropyridine serves as a versatile building block for functionalized pyridine scaffolds in medicinal chemistry and materials science. The ortho-bromine substituents enable palladium-catalyzed cross-coupling reactions, while the electron-withdrawing nitro group enhances electrophilicity at C3, facilitating nucleophilic substitution and enabling sequential derivatization. Bench-stable and readily purified by recrystallization, it functions effectively in multi-step syntheses requiring regioselective transformations.

Safety Information

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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 56.03
LogP 2.5148
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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2,6-Dibromo-3-nitropyridine

CAS No. 55304-80-8

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