(11bR)-4-Hydroxy-2,6-bis(2,4,6-trimethylphenyl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin

Name: (11bR)-4-Hydroxy-2,6-bis(2,4,6-trimethylphenyl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin
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CAS No. 695162-87-9
Cat. No. CS-0091466
Molecule weight584.64
Purity≥97%
MDL No.MFCD31707595

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(11bR)-4-Hydroxy-2,6-bis(2,4,6-trimethylphenyl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin|CS-0091466

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General Information

CAS No. 695162-87-9
Cat. No. CS-0091466
Purity ≥97%
MDL No. MFCD31707595
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₈H₃₃O₄P
Molecular Weight 584.64
Synonym(s) R-4-oxide-4-hydroxy-2,6-bis(2,4,6-triMethylphenyl)-Dinaphtho[2,1-d
SMILES O=P1(O)OC2=C(C3=C(C=CC=C4)C4=CC(C5=C(C)C=C(C)C=C5C)=C3O1)C6=CC=CC=C6C=[C@]2[C@]7=C(C)C=C(C)C=C7C

Description

This sterically encumbered dioxaphosphepin features a chiral 11bR configuration and a hydroxylated, electron-deficient phosphorus center. The ortho-methylated aryl substituents confer exceptional stability and solubility in nonpolar media, enabling robust performance in asymmetric catalysis and transition-metal-free phosphorylation reactions under ambient conditions.

Application

(11bR)-4-Hydroxy-2,6-bis(2,4,6-trimethylphenyl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin serves as a sterically encumbered, bench-stable phosphine oxide with enhanced oxidative stability. It functions as a robust ligand in palladium-catalyzed cross-coupling reactions, enabling efficient C–C bond formation under mild conditions. Its ortho-substituted aryl groups confer high functional group tolerance and facilitate easy purification, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

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 10.7161
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Key Words

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(11bR)-4-Hydroxy-2,6-bis(2,4,6-trimethylphenyl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin

CAS No. 695162-87-9

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