2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane

• ChemBase ID: 143255
• Molecular Formular: C18H39N4P
• Molecular Mass: 342.502821
• Monoisotopic Mass: 342.2912339
• SMILES: CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C
• Canonical SMILES: CC(CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C)C
• InChI: InChI=1S/C18H39N4P/c1-16(2)13-20-10-7-19-8-11-21(14-17(3)4)23(20)22(12-9-19)15-18(5)6/h16-18H,7-15H2,1-6H3
• InChIKey: WFHPXSHLCFHEIA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane
• IUPAC Traditional name: 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane
• Synonyms: 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane solution; Triisobutylphosphatrane; 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane; 2,8,9-三异丁基-2,5,8,9-四氮杂-1-磷杂双环[3.3.3]十一烷 溶液; 2,8,9-三异丁基-2,5,8,9-四氮杂-1-磷杂双环[3.3.3]十一烷

Database IDs

• CAS Number: 331465-71-5
• MDL Number: MFCD03840347
• PubChem SID: 162237476; 24880262
• PubChem CID: 4571243

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.1996914
• LogD (pH = 7.4): 2.7850976
• Log P: 2.9606
• Molar Refractivity: 103.8299 cm^3
• Polarizability: 41.274555 Å^3
• Polar Surface Area: 12.96 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 154.4 °F; 68 °C
• Density: 0.766 g/mL at 25 °C; 0.964 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5020(lit.)

Safety Information

• European Hazard Symbols: Highly flammable (F+); Harmful (Xn)
• UN Number: 1155
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 1
• Risk Statements: 12-19-22-66-67
• Safety Statements: 9-16-29-33
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1155 3/PG 1

Product Information

• Purity: 97%
• Concentration: 0.5 M in diethyl ether
• Empirical Formula (Hill Notation): C18H39N4P

DETAILS

Sigma Aldrich - 710016

Packaging
50 mL in Sure/Seal™

Sigma Aldrich - 565881

Application
Ligand used in the α-arylation of nitriles with aryl bromides and chlorides,1,2 and in the Stille cross-coupling of aryl chlorides.3
Together with Pd2(dba)3 (Catalog Number 328774) forms a highly efficient catalyst for one-pot syntheses of trans-4-N,N-diarylaminostilbenes and N,N-diarylaminostyrenes. Catalyst for methanolic cleavage of heteroaromatic carbamates.
Packaging
1, 5 g in glass bottle