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CS-W001157 4
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(11bS)-N,N,2,6-Tetramethyl-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine

  • CAS No. 185449-86-9

  • Cat. No. CS-0035240
  • Purity≥97%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

(11bS)-N,N,2,6-Tetramethyl-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine|CS-0035240

Structure of 185449-86-9

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General Information

  • CAS No. 185449-86-9
  • Cat. No. CS-0035240
  • Purity ≥97%
  • MDL No. None
  • Storage -20°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₄H₂₂NO₂P
  • Molecular Weight 387.41
  • Synonym(s) N,N,2,6-Tetramethyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine
  • SMILES CC1=CC2=CC=CC=C2[C@@]3=C1OP(N(C)C)OC4=C(C)C=C5C(C=CC=C5)=[C@]34

Description

This sterically encumbered diphosphine ligand features a rigid, electron-rich scaffold that enhances metal coordination stability. The (11bS) stereochemistry ensures predictable chelation geometry, enabling high selectivity in catalytic transformations. Bench-stable and moisture-tolerant, it integrates seamlessly into palladium-catalyzed cross-coupling workflows.

Application

(11bS)-N,N,2,6-Tetramethyl-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine serves as a sterically encumbered, bench-stable phosphine ligand that facilitates palladium-catalyzed cross-coupling reactions. Its rigid binaphthyl framework imparts excellent thermal stability and enhances reactivity in Suzuki-Miyaura and Negishi couplings, particularly with challenging substrates. The tetramethyl substitution pattern improves solubility and reduces aggregation, enabling efficient purification and consistent performance in high-throughput synthetic 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 : H302-H315-H319-H335
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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Computational Chemistry Data

  • TPSA   29.52
  • LogP   7.41084
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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