2,6-Bis[(4S,5S)-4,5-dihydro-4,5-diphenyl-1H-imidazol-2-yl]pyridine

Name: 2,6-Bis[(4S,5S)-4,5-dihydro-4,5-diphenyl-1H-imidazol-2-yl]pyridine
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CAS No. 1221973-02-9
Cat. No. CS-0092960
Molecule weight519.64
Purity≥97%
MDL No.None

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2,6-Bis[(4S,5S)-4,5-dihydro-4,5-diphenyl-1H-imidazol-2-yl]pyridine|CS-0092960

Structure of 1221973-02-9

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General Information

CAS No. 1221973-02-9
Cat. No. CS-0092960
Purity ≥97%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₅H₂₉N₅
Molecular Weight 519.64
Synonym(s) 2,6-bis[(4S,5S)-4,5-dihydro-4,5-diphenyl-1H-imidazol-2-yl]-Pyridine
SMILES C1(C2=N[C@@H](C3=CC=CC=C3)[C@H](C4=CC=CC=C4)N2)=CC=CC(C5=N[C@@H](C6=CC=CC=C6)[C@H](C7=CC=CC=C7)N5)=N1

Description

This pyridine-based ligand features two imidazolyl moieties at the 2,6-positions, each bearing a sterically hindered diphenyl-substituted five-membered ring. The chiral (4S,5S) configuration enhances rigidity and coordination control, enabling precise metal binding in catalytic systems. Bench-stable and moisture-tolerant, it facilitates robust complex formation under standard conditions.

Application

2,6-Bis[(4S,5S)-4,5-dihydro-4,5-diphenyl-1H-imidazol-2-yl]pyridine serves as a sterically demanding, bench-stable chelating ligand that facilitates transition-metal-catalyzed cross-coupling reactions. Its rigid, C₂-symmetric architecture enhances metal coordination stability and promotes high selectivity in palladium-catalyzed transformations. The imidazoline moieties exhibit excellent functional group tolerance and simplify purification through crystalline precipitate formation. This ligand is particularly effective in Suzuki-Miyaura and Negishi coupling protocols under mild conditions.

Safety Information

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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-P280-P302+P352

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Computational Chemistry Data

TPSA 61.67
LogP 6.7464
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 6

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2,6-Bis[(4S,5S)-4,5-dihydro-4,5-diphenyl-1H-imidazol-2-yl]pyridine

CAS No. 1221973-02-9

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