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(11bS)-N,N-Diethyl-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine
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CAS No. 252288-04-3
- Cat. No. CS-0085881
- Purity≥96%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
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Structure of 252288-04-3
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General Information
- CAS No. 252288-04-3
- Cat. No. CS-0085881
- Purity ≥96%
- MDL No. None
- Storage 4°C, protect from light, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₂₄H₂₂NO₂P
- Molecular Weight 387.41
- Synonym(s) (S)-N,N-Diethyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine
- SMILES CCN(CC)P1OC2=[C@]([C@]3=C(C=CC=C4)C4=CC=C3O1)C5=CC=CC=C5C=C2
Description
This bench-stable phosphine features a rigid, electron-rich dioxaphosphepin core with stereodefined (11bS) configuration, enabling predictable reactivity in cross-coupling and catalytic transformations. The N,N-diethyl substitution enhances solubility and reduces oxidation susceptibility, while the fused naphthalene framework imparts thermal resilience and steric protection around the phosphorus center.
Application
(11bS)-N,N-Diethyl-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine serves as a chiral phosphine ligand enabling efficient transition-metal-catalyzed cross-coupling reactions. Its rigid, polycyclic framework imparts high thermal stability and robust functional group tolerance, facilitating reproducible coupling outcomes in palladium-catalyzed transformations. The diethylamino group enhances electron density at phosphorus, improving reactivity in Suzuki-Miyaura and Negishi protocols while maintaining ease of purification and handling under standard laboratory conditions.
Synthesis
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Route1
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14684-28-7 -
In-stock
602-09-5 - ~81%
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In-stock
252288-04-3
References
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Maslennikova, Vera I.; Merkulov, Roman V.; Dyagileva, Maria V.; Vasyanina, Larisa K.; Lyssenko, Konstantin A.; Antipin, Mikhail Yu.; Weber, Dirk; Bauer, Ingmar; Habicher, Wolf D.; Nifantyev, Eduard E. Tetrahedron, 2003 , vol. 59, # 10 p. 1753 - 1761
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References
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Ma, Margaret F. P.; Li, Kangying; Zhou, Zhenghong; Tang, Chuchi; Chan, Albert S. C. Tetrahedron Asymmetry, 1999 , vol. 10, # 17 p. 3259 - 3261
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 29.52
- LogP 7.5742
- H_Acceptors 3
- H_Donors 0
- Rotatable_Bonds 3
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Key Words
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