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

Name: (11bS)-N,N-Bis[(1S)-1-(1-naphthalenyl)ethyl]dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine
Brand: ChemScene
Availability: InStock
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CAS No. 342813-26-7
Cat. No. CS-0129003
Purity≥95%
MDL No.None

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(11bS)-N,N-Bis[(1S)-1-(1-naphthalenyl)ethyl]dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine|CS-0129003

Structure of 342813-26-7

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Description

This chiral phosphine ligand features a rigid dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin scaffold with two sterically demanding naphthylethyl substituents. The (11bS) stereochemistry and N,N-bis(1-naphthalenylethyl) groups confer exceptional enantioselectivity in palladium-catalyzed cross-coupling reactions. Bench-stable and moisture-tolerant, it integrates seamlessly into asymmetric synthesis workflows.

Application

(11bS)-N,N-Bis[(1S)-1-(1-naphthalenyl)ethyl]dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine serves as a sterically encumbered, bench-stable chiral phosphine ligand that enables efficient transition-metal-catalyzed cross-coupling reactions. Its rigid dinaphtho scaffold and tertiary amine functionality confer excellent functional group tolerance and reproducible catalytic performance in Pd-catalyzed Suzuki-Miyaura and Negishi couplings, facilitating the construction of complex biaryl and heterocyclic architectures with high enantioselectivity.

General Information

CAS No. 342813-26-7
Cat. No. CS-0129003
Purity ≥95%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄₄H₃₄NO₂P
Molecular Weight 639.72
Synonym(s) None
SMILES C[C@@H](C1=C(C=CC=C2)C2=CC=C1)N([C@H](C3=CC=CC4=C3C=CC=C4)C)P5OC6=[C@]([C@]7=C(C=CC=C8)C8=CC=C7O5)C9=CC=CC=C9C=C6

Computational Chemistry Data

TPSA 29.52
LogP 13.3632
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 5

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-P280-P302+P352

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

CAS No. 342813-26-7

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