Lot numbers can be found on the outside label of a product:
4,4',6,6'-Tetramethyl-2,2'-bipyridine
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CAS No. 4444-27-3
- Cat. No. CS-0203107
- Purity≥98%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 4444-27-3
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General Information
- CAS No. 4444-27-3
- Cat. No. CS-0203107
- Purity ≥98%
- MDL No. None
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₄H₁₆N₂
- Molecular Weight 212.29
- Synonym(s) 2-(4,6-dimethylpyridin-2-yl)-4,6-dimethylpyridine
- SMILES CC1=NC(C2=CC(C)=CC(C)=N2)=CC(C)=C1
Description
4,4',6,6'-Tetramethyl-2,2'-bipyridine is a sterically hindered bipyridine ligand featuring methyl groups at the 4,4',6,6' positions. This substitution pattern enhances solubility in organic solvents and improves stability under ambient conditions. The molecule serves as an effective chelating agent for transition metals, particularly in catalytic systems requiring controlled coordination geometry. Its electron-rich character facilitates metal-ligand interactions while resisting oxidation.
Application
4,4',6,6'-Tetramethyl-2,2'-bipyridine serves as a robust chelating ligand in transition metal catalysis, particularly in palladium- and copper-mediated cross-coupling reactions. Its methyl substituents enhance solubility and steric protection, improving catalyst stability and selectivity. The ligand facilitates efficient C–C and C–heteroatom bond formations under mild conditions, offering reliable performance in synthetic workflows requiring functional group tolerance and ease of purification.
Synthesis
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Route1
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In-stock
4926-26-5 - ~12%
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In-stock
4444-27-3
References
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Mukkala, Veli-Matti; Kankare, Jouko J. Helvetica Chimica Acta, 1992 , vol. 75, # 5 p. 1578 - 1592
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Route2
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108-47-4 - ~33%
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In-stock
4444-27-3
References
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Shaw, Anthony P.; Wragg, David S.; Jakobsen, Soren; Ghosh, Manik Kumer; Swang, Ole; Heyn, Richard H.; Toernroos, Karl W.; Tilset, Mats Organometallics, 2012 , vol. 31, # 20 p. 7093 - 7100,8
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Route3
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In-stock
5407-87-4 - ~%
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In-stock
4444-27-3
References
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Mukkala, Veli-Matti; Kankare, Jouko J. Helvetica Chimica Acta, 1992 , vol. 75, # 5 p. 1578 - 1592
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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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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Quality Control
Computational Chemistry Data
- TPSA 25.78
- LogP 3.37728
- H_Acceptors 2
- H_Donors 0
- Rotatable_Bonds 1
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Key Words
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