(11bS)-4-Hydroxy-2,6-bis([1,1':3',1''-terphenyl]-5'-yl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin

Name: (11bS)-4-Hydroxy-2,6-bis([1,1':3',1''-terphenyl]-5'-yl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin
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CAS No. 1496637-05-8
Cat. No. CS-0084544
Purity≥95%
MDL No.None

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(11bS)-4-Hydroxy-2,6-bis([1,1':3',1''-terphenyl]-5'-yl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin|CS-0084544

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General Information

CAS No. 1496637-05-8
Cat. No. CS-0084544
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 C₅₆H₃₇O₄P
Molecular Weight 804.86
Synonym(s) (S)-3,3'-Bis(3,5-diphenyl)phenyl-1,1'-binaphthyl-2,2'-diyl Hydrogen Phosphate
SMILES OP1(OC2=C(C3=CC=CC=C3C=C2C4=CC(C5=CC=CC=C5)=CC(C6=CC=CC=C6)=C4)C7=C(C(C8=CC(C9=CC=CC=C9)=CC(C%10=CC=CC=C%10)=C8)=CC%11=CC=CC=C7%11)O1)=O

Description

This sterically encumbered phosphine oxide features a rigid, electron-deficient terphenyl scaffold that enhances oxidative stability and facilitates ligand design in transition metal catalysis. The 11bS stereochemistry ensures defined spatial orientation for asymmetric synthesis applications.

Application

(11bS)-4-Hydroxy-2,6-bis([1,1':3',1''-terphenyl]-5'-yl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin serves as a sterically encumbered, bench-stable phosphine ligand that facilitates palladium-catalyzed cross-coupling reactions under mild conditions. Its rigid terphenyl architecture provides exceptional resistance to oxidation and enables efficient catalyst turnover in Suzuki-Miyaura and Negishi couplings. The hydroxyl group enhances solubility and aids in purification without compromising reactivity.

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 15.5336
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 6

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(11bS)-4-Hydroxy-2,6-bis([1,1':3',1''-terphenyl]-5'-yl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin

CAS No. 1496637-05-8

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