2-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridine

Name: 2-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridine
Brand: ChemScene
Availability: InStock
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CAS No. 49669-14-9
Cat. No. CS-0153767
Purity≥95%
MDL No.MFCD12406888

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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-6-(2-methyl-1,3-dioxolan-2-yl)pyridine|CS-0153767

Structure of 49669-14-9

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General Information

CAS No. 49669-14-9
Cat. No. CS-0153767
Purity ≥95%
MDL No. MFCD12406888
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₀BrNO₂
Molecular Weight 244.09
Synonym(s) None
SMILES CC1(C2=NC(=CC=C2)Br)OCCO1

Description

2-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridine features a brominated pyridine core paired with a stable 2-methyl-1,3-dioxolane protecting group, enabling selective functionalization in cross-coupling reactions. The dioxolane moiety enhances solubility and stability under standard conditions, while the bromide serves as a reliable coupling handle for palladium-mediated transformations.

Application

2-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridine serves as a versatile building block in cross-coupling chemistry, enabling efficient Pd-catalyzed transformations to access substituted pyridine scaffolds. The 1,3-dioxolan-2-yl group provides excellent stability and mild deprotection conditions, while the bromide facilitates reliable Suzuki, Stille, and Negishi couplings. Its bench-stable nature and compatibility with diverse functional groups make it ideal for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

Route1
- In-stock
  
  49669-13-8
- In-stock
  
  107-21-1
- ~87%
- In-stock
  
  49669-14-9
References
- Ronson, Tanya K.; Adams, Harry; Harding, Lindsay P.; Pope, Simon J. A.; Sykes, Daniel; Faulkner, Stephen; Ward, Michael D. Dalton Transactions, 2007 , # 10 p. 1006 - 1022
Route2
- In-stock
  
  626-05-1
- ~%
- In-stock
  
  49669-14-9
References
- Poellnitz, Alpar; Skupienski, Radek; Stoeckli-Evans, Helen; Crochet, Aurelien; Silvestru, Anca; Fromm, Katharina M.; Mamula, Olimpia Synlett, 2013 , vol. 24, # 19 art. no. ST-2013-B0678-L, p. 2555 - 2558

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

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Computational Chemistry Data

TPSA 31.35
LogP 2.0636
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Dioxolane compounds

Key Words

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2-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridine

CAS No. 49669-14-9

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