463558
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:
Molecular Weight:
216.26
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4970285
InChI
1S/C9H21N4P/c1-10-4-7-13-8-5-11(2)14(10)12(3)6-9-13/h4-9H2,1-3H3
SMILES string
CN1CCN2CCN(C)P1N(C)CC2
InChI key
PCYSWBQHCWWSFW-UHFFFAOYSA-N
mp
110-115 °C (lit.)
Quality Level
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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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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)
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)
(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)
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)
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