Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

463558

Sigma-Aldrich

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

Synonym(s):

Verkade superbase

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Looking for similar products? Visit Product Comparison Guide

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCS5719
MKCC4843
MKBS5439V
MKBH2139V
MKBC7799

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

[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)
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)
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)
(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)
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service