(11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide

Name: (11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide
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CAS No. 1043567-32-3
Cat. No. CS-0030474
Purity≥98%
MDL No.None

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(11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide|CS-0030474

Structure of 1043567-32-3

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General Information

CAS No. 1043567-32-3
Cat. No. CS-0030474
Purity ≥98%
MDL No. None
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄₈H₂₉O₄P
Molecular Weight 700.72
Synonym(s) (S)-3,3'-Bis(9-phenanthrenyl)-1,1'-binaphthyl-2,2'-diyl Hydrogen Phosphate
SMILES OP1(OC2=C(C3=CC=CC=C3C=C2C4=C5C(C=CC=C5)=C6C(C=CC=C6)=C4)C7=C(C(C8=C(C=CC=C9)C9=C(C=CC=C%10)C%10=C8)=CC%11=CC=CC=C7%11)O1)=O

Description

This sterically encumbered phosphine oxide features a rigid, polycyclic framework that enhances thermal stability and resistance to oxidation. The 4-hydroxy group enables hydrogen bonding and modulates electronic properties, while the phenanthrenyl substituents provide extended π-conjugation and steric shielding around the phosphorus center. This structure facilitates controlled coordination in catalytic systems and improves performance in air-sensitive transformations under standard bench conditions.

Application

(11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide serves as a sterically encumbered, bench-stable phosphine oxide scaffold with defined stereochemistry at the 11b position. It functions as a versatile building block in transition-metal-catalyzed cross-coupling reactions and enables precise control in the synthesis of complex polycyclic architectures. Its hydroxyl group provides a handle for derivatization, while the phenanthrene substituents enhance rigidity and electronic modulation, offering improved functional group tolerance and reproducibility in catalytic systems.

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 13.4784
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Key Words

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(11bS)-4-Hydroxy-2,6-di(phenanthren-9-yl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide

CAS No. 1043567-32-3

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