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  • 463558 - 2,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane

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463558 Sigma-Aldrich

2,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane

Synonym: Verkade superbase

  • CAS Number 120666-13-9

  • Empirical Formula (Hill Notation) C9H21N4P

  • Molecular Weight 216.26

  •  Beilstein/REAXYS Number 4970285

  •  MDL number MFCD00269837

  •  PubChem Substance ID 24870079

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Properties

Related Categories Acids & Bases, Bases, Chemical Synthesis, Organic Bases, Synthetic Reagents More...
InChI Key   PCYSWBQHCWWSFW-UHFFFAOYSA-N
mp   110-115 °C (lit.)

Description

Application

2,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane is involved as a reactant in:
• Studies of N-heterocyclic carbene ligand effects on metal hydride bond energies.
• Synthesis of heterogenous basic catalysts immobilized on SBA-15 silica.
• Protection / deprotection strategies for diazeniumdiolate chemistry.
• Encaging of the molecule to study the change in its catalytic ability.
• C-N coupling reactions.
• Derivative synthesis used as a promoter for aza and thia-Michael reaction and Strecker reaction.

Reactant involved in:
• Studies of N-heterocyclic carbene ligand effects on metal hydride bond energies
• Synthesis of heterogenous basic catalysts immobilized on SBA-15 silica
• Protection / deprotection strategies for diazeniumdiolate chemistry
• Encaging of the molecule to study change in its catalytic ability
• C-N coupling reactions
• Derivative synthesis used as a promoter for aza and thia-Michael reaction and Strecker reaction

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis

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Protocols & Articles

Articles

Proazaphosphatranes: Verkade’s Superbases

Sigma-Aldrich is pleased to offer Verkade’s Superbases. For a recent survey of the applications of proazaphosphatranes in organic synthesis, see Aldrichimica Acta, 2004, 37(1).
ChemFiles Volume 4 Article 2
Keywords: Aldrichimica Acta, Applications, Organic synthesis

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Peer-Reviewed Papers
15

References

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