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

Name: (11bS)-N,N-Bis[(1R)-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. 342813-25-6
Cat. No. CS-0129004
Purity≥95%
MDL No.None

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(11bS)-N,N-Bis[(1R)-1-(1-naphthalenyl)ethyl]dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine|CS-0129004

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General Information

CAS No. 342813-25-6
Cat. No. CS-0129004
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) 3,4-a']dinaphthalen-4-yl)bis[(1R)-1-(1-naphthalenyl)ethyl]aMine
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

Description

This chiral phosphine amine features a rigid dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin scaffold with two naphthalenyl-ethyl substituents in defined stereochemistry. Designed for asymmetric catalysis, it delivers high enantioselectivity in transition metal-mediated transformations. The sterically tuned pocket and electron-rich phosphorus center enable precise substrate control under standard conditions.

Application

(11bS)-N,N-Bis[(1R)-1-(1-naphthalenyl)ethyl]dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine serves as a sterically encumbered, chiral phosphine ligand that enables high-yielding transition-metal-catalyzed cross-coupling reactions. Its rigid dinaphtho scaffold provides excellent thermal stability and robust functional group tolerance, facilitating efficient palladium-catalyzed Suzuki and Negishi couplings under mild conditions. The ligand’s defined stereochemistry enhances enantioselectivity in asymmetric transformations, making it particularly valuable for the synthesis of complex pharmaceutical intermediates and functionalized biaryl architectures.

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 : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 29.52
LogP 13.3632
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 5

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

CAS No. 342813-25-6

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