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463558

Sigma-Aldrich

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

Synonym(s):

Verkade superbase

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About This Item

Empirical Formula (Hill Notation):
C9H21N4P
CAS Number:
120666-13-9
Molecular Weight:
216.26
Beilstein:
4970285
MDL number:
MFCD00269837
UNSPSC Code:
12352005
PubChem Substance ID:
24870079
NACRES:
NA.22

mp

110-115 °C (lit.)

Quality Level

100

SMILES string

CN1CCN2CCN(C)P1N(C)CC2

InChI

1S/C9H21N4P/c1-10-4-7-13-8-5-11(2)14(10)12(3)6-9-13/h4-9H2,1-3H3

InChI key

PCYSWBQHCWWSFW-UHFFFAOYSA-N

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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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A new step towards solid base catalysis: azidoproazaphosphatranes immobilized in nanopores of mesoporous silica.
Raytchev P D, et al.
advanced synthesis and catalysis, 353(11?12), 2067-2077 (2011)
Comprehensive Thermochemistry of W?H Bonding in the Metal Hydrides CpW (CO) 2 (IMes) H,[CpW (CO) 2 (IMes) H]?+, and [CpW (CO) 2 (IMes)(H) 2]+. Influence of an N-Heterocyclic Carbene Ligand on Metal Hydride Bond Energies.
Roberts J A, et al.
Journal of the American Chemical Society, 133(37), 14604-14613 (2011)
Novel protection?deprotection strategies in diazeniumdiolate chemistry: synthesis of V-IPA/NO.
Nandurdikar R S, et al.
Chemical Communications (Cambridge, England), 47(23), 6710-6712 (2011)
(t-Bu) 2PN P (i-BuNCH2CH2) 3N: New Efficient Ligand for Palladium-Catalyzed C? N Couplings of Aryl and Heteroaryl Bromides and Chlorides and for Vinyl Bromides at Room Temperature.
Reddy C V, et al.
The Journal of Organic Chemistry, 73(8), 3047-3062 (2008)
Encaging the Verkade?s superbases: thermodynamic and kinetic consequences.
Raytchev P D, et al.
Journal of the American Chemical Society, 133(7), 2157-2159 (2011)
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