N,N-Bis[(1R)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine

Name: N,N-Bis[(1R)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine
Brand: ChemScene
Availability: InStock
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CAS No. 500103-26-4
Cat. No. CS-0035270
Purity≥97%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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N,N-Bis[(1R)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine|CS-0035270

Structure of 500103-26-4

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Description

N,N-Bis[(1R)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine is a chiral phosphine ligand featuring a rigid, electron-rich dioxaphosphepin scaffold. This structure imparts exceptional stability and defined stereochemistry, enabling high enantioselectivity in transition metal-catalyzed asymmetric reactions. The bulky phenylethyl substituents provide steric shielding around the phosphorus center, enhancing catalyst performance and resistance to oxidation under standard conditions.

Application

N,N-Bis[(1R)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine serves as a sterically hindered, chiral phosphine ligand that enables efficient transition-metal-catalyzed cross-coupling reactions. Its rigid dibenzo-dioxaphosphepin core provides enhanced thermal stability and resistance to oxidation, while the bulky (1R)-1-phenylethyl groups promote high enantioselectivity in asymmetric transformations. The amine functionality facilitates coordination to palladium and nickel centers, supporting catalytic cycles in Suzuki-Miyaura and Negishi couplings with excellent functional group tolerance and ease of purification.

General Information

CAS No. 500103-26-4
Cat. No. CS-0035270
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 C₂₈H₂₆NO₂P
Molecular Weight 439.49
Synonym(s) N,N-bis[(1S)-1-phenylethyl]-Dibenzo[d,f][1,3,2]dioxaphosphepin-6-aMine
SMILES C[C@H](C1=CC=CC=C1)N([C@H](C)C2=CC=CC=C2)P3OC4=C(C5=CC=CC=C5O3)C=CC=C4

Computational Chemistry Data

TPSA 29.52
LogP 8.7504
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 5

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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N,N-Bis[(1R)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine

CAS No. 500103-26-4

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