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

Name: (11bR)-N,N-Bis(1-methylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine
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CAS No. 239113-47-4
Cat. No. CS-0088776
Purity≥97%
MDL No.None

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(11bR)-N,N-Bis(1-methylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine|CS-0088776

Structure of 239113-47-4

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General Information

CAS No. 239113-47-4
Cat. No. CS-0088776
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) None
SMILES CC(C)N(C(C)C)P1OC2=C(C3=C(C=CC=C4)C4=CC=C3O1)C5=CC=CC=C5C=C2

Description

This chiral phosphine amine features a rigid dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin scaffold with (11bR) stereochemistry, offering enhanced stability and defined steric profile. The N,N-bis(1-methylethyl) substituents provide steric bulk while maintaining solubility in common organic solvents. This configuration enables effective coordination in asymmetric catalysis, particularly in palladium-catalyzed cross-coupling reactions where controlled ligand geometry is essential.

Application

(11bR)-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 imparts high thermal stability and enhances selectivity in Suzuki-Miyaura and Negishi transformations. The tertiary amine functionality enables efficient coordination to transition metals while maintaining compatibility with diverse functional groups, making it well-suited for complex molecule synthesis and scale-up applications.

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-P330-P362+P364-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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(11bR)-N,N-Bis(1-methylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine

CAS No. 239113-47-4

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