3-Bromo-N,N-dimethylpyridin-4-amine

Name: 3-Bromo-N,N-dimethylpyridin-4-amine
Brand: ChemScene
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CAS No. 84539-35-5
Cat. No. CS-0151309
Purity≥97%
MDL No.MFCD09743635

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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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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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3-Bromo-N,N-dimethylpyridin-4-amine|CS-0151309

Structure of 84539-35-5

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General Information

CAS No. 84539-35-5
Cat. No. CS-0151309
Purity ≥97%
MDL No. MFCD09743635
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₉BrN₂
Molecular Weight 201.06
Synonym(s) 3-BROMO-4-(N,N-DIMETHYL)AMINOPYRIDINE
SMILES CN(C)C1=CC=NC=C1Br

Description

3-Bromo-N,N-dimethylpyridin-4-amine features a pyridine core functionalized with a bromo group at the 3-position and dimethylamino substitution at the 4-position. This combination delivers enhanced reactivity in cross-coupling processes, enabling efficient C–C and C–heteroatom bond formation. The electron-rich dimethylamino group stabilizes intermediates under transition metal catalysis, while the bromide serves as a reliable coupling handle. This compound excels in synthesizing complex heterocyclic architectures and bioactive molecules.

Application

3-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 functionalization at the C3 position, while the N,N-dimethylpyridin-4-amine moiety provides enhanced solubility and stability. This compound is particularly valuable for constructing substituted pyridine scaffolds found in pharmaceutical intermediates.

Synthesis

Route1
- 1122-58-3
- ~94%
- In-stock
  
  84539-35-5
References
- Paudler, William W.; Jovanovic, Misa V. Journal of Organic Chemistry, 1983 , vol. 48, # 7 p. 1064 - 1069
Route2
- In-stock
  
  1005-31-8
- ~7%
- 84539-40-2
- In-stock
  
  84539-35-5
References
- Journal of Organic Chemistry, , vol. 48, # 7 p. 1064 - 1069
Route3
- 67-56-1
- 139111-73-2
- ~0%
- In-stock
  
  84539-35-5
- 121-45-9
References
- Bezgubenko; Pipko; Sinitsa Russian Journal of General Chemistry, 2009 , vol. 79, # 5 p. 911 - 918

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

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3-Bromo-N,N-dimethylpyridin-4-amine

CAS No. 84539-35-5

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