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

Name: (11bR)-4-Hydroxy-2,6-bis[4-(trifluoromethyl)phenyl]-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin
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CAS No. 791616-59-6
Cat. No. CS-0090627
Purity≥97%
MDL No.MFCD17676196

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(11bR)-4-Hydroxy-2,6-bis[4-(trifluoromethyl)phenyl]-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin|CS-0090627

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General Information

CAS No. 791616-59-6
Cat. No. CS-0090627
Purity ≥97%
MDL No. MFCD17676196
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₄H₁₉F₆O₄P
Molecular Weight 636.48
Synonym(s) None
SMILES O=P1(O)OC2=C(C3=C(C=CC=C4)C4=CC(C5=CC=C(C(F)(F)F)C=C5)=C3O1)C6=CC=CC=C6C=C2C7=CC=C(C(F)(F)F)C=C7

Description

This sterically encumbered phosphine oxide features a rigid dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin core with a (11bR)-configured hydroxy group and two para-trifluoromethylphenyl substituents. The electron-withdrawing trifluoromethyl groups enhance oxidative stability while the oxygenated scaffold promotes solubility in polar organic media. This structure enables efficient coupling reactions under mild conditions.

Application

(11bR)-4-Hydroxy-2,6-bis[4-(trifluoromethyl)phenyl]-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin serves as a sterically encumbered, bench-stable phosphine oxide scaffold with enhanced oxidative stability. Its structure enables controlled reactivity in transition-metal-catalyzed cross-coupling processes, particularly in Pd-catalyzed Suzuki-Miyaura and Negishi reactions. The trifluoromethyl aryl groups confer high electron-withdrawing character and improve solubility in organic media, facilitating purification and handling during multi-step synthesis of complex heterocyclic systems and functionalized scaffolds.

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-P280-P302+P352-P304+P340

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Computational Chemistry Data

TPSA 55.76
LogP 10.9032
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Key Words

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

CAS No. 791616-59-6

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