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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)

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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 & Catalysis, 353(11?12), 2067-2077 (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)
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)
(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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Articles

Proazaphosphatranes: Verkade’s Superbases

An article on Proazaphosphatranes: Verkade’s Superbases.

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