(11bS)-N,N-Bis(1-methylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine

Name: (11bS)-N,N-Bis(1-methylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine
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CAS No. 185449-85-8
Cat. No. CS-0090813
Purity≥97%
MDL No.None

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(11bS)-N,N-Bis(1-methylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine|CS-0090813

Structure of 185449-85-8

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General Information

CAS No. 185449-85-8
Cat. No. CS-0090813
Purity ≥97%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₆H₂₆NO₂P
Molecular Weight 415.46
Synonym(s) O,O′-(1,1′-dinaphthyl-2,2′-diyl)-N,N-di-iso-propylethylphosphoramidite
SMILES CC(C)N(C(C)C)P1OC2=[C@]([C@]3=C(C=CC=C4)C4=CC=C3O1)C5=CC=CC=C5C=C2

Description

This sterically encumbered phosphine ligand features a rigid dinaphtho scaffold with a chiral (11bS) configuration, enabling high enantioselectivity in palladium-catalyzed cross-coupling reactions. The N,N-bis(1-methylethyl) substituents enhance stability and solubility while minimizing aggregation.

Application

(11bS)-N,N-Bis(1-methylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine serves as a sterically hindered, bench-stable phosphine ligand that facilitates palladium-catalyzed cross-coupling reactions. Its rigid binaphthyl framework and tertiary amine functionality enhance electron donation and stability under oxidative conditions, enabling efficient coupling in challenging substrates. Ideal for Suzuki-Miyaura and Buchwald-Hartwig transformations, it offers predictable performance with minimal decomposition during purification and scale-up.

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-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 29.52
LogP 8.3512
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 3

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(11bS)-N,N-Bis(1-methylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine

CAS No. 185449-85-8

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