2-Bromo-4,5-dimethylpyridine

Name: 2-Bromo-4,5-dimethylpyridine
Brand: ChemScene
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CAS No. 66533-31-1
Cat. No. CS-0312088
Purity≥97%
MDL No.MFCD11869962

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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 66533-31-1

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General Information

CAS No. 66533-31-1
Cat. No. CS-0312088
Purity ≥97%
MDL No. MFCD11869962
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₈BrN
Molecular Weight 186.05
Synonym(s) 2-Bromo-4,5-lutidine
SMILES CC1=CN=C(Br)C=C1C

Description

2-Bromo-4,5-dimethylpyridine is a bench-stable, electron-deficient heterocycle featuring two methyl groups at the 4- and 5-positions. This substitution pattern enhances regioselectivity in cross-coupling reactions, enabling efficient construction of complex pyridyl architectures. The bromine atom serves as a reliable handle for palladium-catalyzed transformations, facilitating direct functionalization in medicinal chemistry and materials synthesis.

Application

2-Bromo-4,5-dimethylpyridine serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig aminations. Its electron-rich pyridine core and bromine substituent offer favorable reactivity for C–C and C–N bond formation, while the methyl groups enhance stability and solubility. The compound exhibits robust bench stability and is readily purified by flash chromatography or recrystallization, facilitating integration into multi-step syntheses of heterocyclic scaffolds and functionalized aryl derivatives.

Synthesis

Route1
- 583-58-4
- ~19%
- In-stock
  
  66533-31-1
- In-stock
  
  33204-85-2
References
- Bayer Scherring Pharma Aktiengellschaft Patent: US2010/93803 A1, 2010 ; Location in patent: Page/Page column 23 ; US 20100093803 A1
Route2
- 583-58-4
- ~80%
- In-stock
  
  66533-31-1
References
- Kaminski, Thomas; Gros, Philippe; Fort, Yves European Journal of Organic Chemistry, 2003 , # 19 p. 3855 - 3860

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H227-H315-H319
Precautionary Statements : P210-P264-P280-P302+P352-P362-P370+P378-P501

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Computational Chemistry Data

TPSA 12.89
LogP 2.46094
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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2-Bromo-4,5-dimethylpyridine

CAS No. 66533-31-1

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