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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:
120666-13-9
Molecular Weight:
216.26
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24870079
MDL number:
MFCD00269837
Beilstein/REAXYS Number:
4970285
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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

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCS5719
MKCC4843
MKBS5439V
MKBH2139V
MKBC7799

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[HP (HNCH2CH2) 3N] NO3: an efficient homogeneous and solid-supported promoter for aza and thia-Michael reactions and for Strecker reactions.
Fetterly B M, et al.
Tetrahedron, 62(2-3), 440-456 (2006)
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)
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Global Trade Item Number

SKUGTIN
463558-5G04061833432167
463558-1G04061826723845