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

• ChemBase ID: 139311
• Molecular Formular: C9H21N4P
• Molecular Mass: 216.263601
• Monoisotopic Mass: 216.15038332
• SMILES: CN1CCN2CCN(P1N(CC2)C)C
• Canonical SMILES: CN1CCN2CCN(P1N(C)CC2)C
• InChI: InChI=1S/C9H21N4P/c1-10-4-7-13-8-5-11(2)14(10)12(3)6-9-13/h4-9H2,1-3H3
• InChIKey: PCYSWBQHCWWSFW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,8,9-trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane
• IUPAC Traditional name: 2,8,9-trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane
• Synonyms: Verkade superbase; 2,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane; Verkade 超强碱; 2,8,9-三甲基-2,5,8,9-四氮杂-1-磷杂双环[3.3.3]十一烷

Database IDs

• CAS Number: 120666-13-9
• MDL Number: MFCD00269837
• Beilstein Number: 4970285
• PubChem SID: 24870079; 162233559
• PubChem CID: 4186723

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -3.3745239
• LogD (pH = 7.4): -1.2435225
• Log P: -0.6811
• Molar Refractivity: 62.5973 cm^3
• Polarizability: 24.675268 Å^3
• Polar Surface Area: 12.96 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 110-115 °C(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C9H21N4P

DETAILS

Sigma Aldrich - 463558

Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Studies of N-heterocyclic carbene ligand effects on metal hydride bond energies1
• Synthesis of heterogenous basic catalysts immobilized on SBA-15 silica2
• Protection / deprotection strategies for diazeniumdiolate chemistry3
• Encaging of the molecule to study change in its catalytic ability4
• C-N coupling reactions5
• Derivative synthesis used as a promoter for aza and thia-Michael reaction and Strecker reaction6