2-Bromo-N,N-dimethylpyridin-4-amine

Name: 2-Bromo-N,N-dimethylpyridin-4-amine
Brand: ChemScene
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CAS No. 396092-82-3
Cat. No. CS-W005087
Purity≥97%
MDL No.MFCD11036210

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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+
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2-Bromo-N,N-dimethylpyridin-4-amine|CS-W005087

Structure of 396092-82-3

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General Information

CAS No. 396092-82-3
Cat. No. CS-W005087
Purity ≥97%
MDL No. MFCD11036210
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₉BrN₂
Molecular Weight 201.06
Synonym(s) 2-Bromo-N,N-diméthyl-4-pyridinamine
SMILES CN(C)C1=CC(Br)=NC=C1

Description

2-Bromo-N,N-dimethylpyridin-4-amine features a pyridine core bearing a bromo substituent at the 2-position and a dimethylamino group at the 4-position, delivering enhanced electrophilicity and tunable reactivity. This configuration enables efficient coupling in cross-coupling processes, particularly in Pd-catalyzed transformations where the electron-deficient pyridine ring facilitates oxidative addition. The dimethylamino group stabilizes intermediates through resonance while maintaining compatibility with diverse reaction conditions. This compound serves as a valuable scaffold for constructing complex heterocyclic architectures in medicinal chemistry and materials science.

Application

2-Bromo-N,N-dimethylpyridin-4-amine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings. The bromo group facilitates efficient C–C and C–N bond formation, while the dimethylamino pyridine moiety provides enhanced solubility and stability. Its bench-stable nature and compatibility with diverse functional groups make it ideal for constructing complex heterocyclic scaffolds and API intermediates.

Synthesis

Route1
- 1122-58-3
- ~91%
- In-stock
  
  396092-82-3
References
- Cuperly, David; Gros, Philippe; Fort, Yves Journal of Organic Chemistry, 2002 , vol. 67, # 1 p. 238 - 241
Route2
- In-stock
  
  58530-53-3
- 124-40-3
- ~80%
- In-stock
  
  396092-82-3
References
- PFIZER LIMITED Patent: WO2007/57775 A1, 2007 ; Location in patent: Page/Page column 159-160 ; WO 2007/057775 A1

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 16.13
LogP 1.9101
H_Acceptors 2
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-Bromo-N,N-dimethylpyridin-4-amine

CAS No. 396092-82-3

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