(11bR)-2,6-Bis[4-(1,1-dimethylethyl)phenyl]-4-hydroxy-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin

Name: (11bR)-2,6-Bis[4-(1,1-dimethylethyl)phenyl]-4-hydroxy-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin
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CAS No. 861909-30-0
Cat. No. CS-0090629
Purity≥97%
MDL No.MFCD27920532

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(11bR)-2,6-Bis[4-(1,1-dimethylethyl)phenyl]-4-hydroxy-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin|CS-0090629

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General Information

CAS No. 861909-30-0
Cat. No. CS-0090629
Purity ≥97%
MDL No. MFCD27920532
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄₀H₃₇O₄P
Molecular Weight 612.69
Synonym(s) (R)-3,3'-Bis(4-tert-butylphenyl)-1,1'-binaphthyl-2,2'-diyl Hydrogen Phosphate
SMILES O=P1(O)OC2=C(C3=C(C=CC=C4)C4=CC(C5=CC=C(C(C)(C)C)C=C5)=C3O1)C6=CC=CC=C6C=C2C7=CC=C(C(C)(C)C)C=C7

Description

This sterically encumbered phosphine oxide features a rigid, fused dioxaphosphepin core with two bulky 4-tert-butylphenyl groups flanking the phosphorus center. The 11bR stereochemistry and hydroxy-oxide functionality confer exceptional bench stability and resistance to oxidation. This structure enables efficient coupling in palladium-catalyzed cross-coupling reactions under mild conditions.

Application

(11bR)-2,6-Bis[4-(1,1-dimethylethyl)phenyl]-4-hydroxy-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin serves as a sterically hindered, bench-stable phosphine oxide that facilitates Pd-catalyzed cross-coupling reactions under mild conditions. Its rigid, electron-rich architecture enhances reactivity in Suzuki-Miyaura and Negishi transformations, while the bulky tert-butyl aryl groups provide exceptional functional group tolerance and ease of purification. This compound functions as a robust building block for complex heterocyclic scaffolds in medicinal chemistry and materials science 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 : H315
Precautionary Statements : P264-P280-P302+P352-P362

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Computational Chemistry Data

TPSA 55.76
LogP 11.4606
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

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(11bR)-2,6-Bis[4-(1,1-dimethylethyl)phenyl]-4-hydroxy-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin

CAS No. 861909-30-0

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