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

• ChemBase ID: 142369
• Molecular Formular: C15H33N4P
• Molecular Mass: 300.423081
• Monoisotopic Mass: 300.24428371
• SMILES: CC(C)N1CCN2CCN(P1N(CC2)C(C)C)C(C)C
• Canonical SMILES: CC(N1CCN2CCN(P1N(CC2)C(C)C)C(C)C)C
• InChI: InChI=1S/C15H33N4P/c1-13(2)17-10-7-16-8-11-18(14(3)4)20(17)19(12-9-16)15(5)6/h13-15H,7-12H2,1-6H3
• InChIKey: DFRWCJYSXGNOFD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,8,9-tris(propan-2-yl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane
• IUPAC Traditional name: 2,8,9-triisopropyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane
• Synonyms: [2,5,8,9-Tetraaza-1-phosphabicyclo[3.3.3]undecane-2,8,9-tris(1-methylethyl)]; 2,8,9-Triisopropyl-2,5,8,9-tetraaza-1-phosphabicyclo[3,3,3]undecane; 2,8,9-Triisopropyl-2,5,8,9-tetraza-1-phosphabicyclo[3.3.3]undecane solution; 2,8,9-三异丙基-2,5,8,9-四硫唑嘌呤-1-磷杂双环[3,3,3]十一烷; [2,5,8,9-四氮杂-1-磷杂双环[3.3.3]十一烷-2,8,9-三(1-甲基乙基)]; 2,8,9-三异丙基-2,5,8,9-四硫唑嘌呤-1-磷杂二环[3.3.3]十一烷 溶液

Database IDs

• CAS Number: 175845-21-3
• MDL Number: MFCD03701530
• PubChem SID: 24879596; 24884031; 162236599
• PubChem CID: 5148322

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.43986607
• LogD (pH = 7.4): 1.3340977
• Log P: 1.5857
• Molar Refractivity: 90.0995 cm^3
• Polarizability: 35.739136 Å^3
• Polar Surface Area: 12.96 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 185 °F; 44.6 °F; 7 °C; 85 °C
• Density: 0.897 g/mL at 25 °C; 0.922 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4830(lit.)

Safety Information

• European Hazard Symbols: Flammable (F); Harmful (Xn)
• UN Number: 1294
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 63-11-38-48/20-65-67
• Safety Statements: 16-36/37-62
• GHS Pictograms: GHS02; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H304-H315-H336-H361d-H373
• GHS Precautionary statements: P210-P261-P281-P301 + P310-P331
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1294 3/PG 2

Product Information

• Concentration: 1 M in toluene
• Linear Formula: PN(CH(CH3)2)CH2CH2NCH2CH2N(CH(CH3)2)(CH2CH2N(CH(CH3)2))
• Empirical Formula (Hill Notation): C15H33N4P

DETAILS

Sigma Aldrich - 654353

Packaging
10 mL in glass bottle

Sigma Aldrich - 556955

Application
Catalyst used in the synthesis of β-hydroxyesters and α,β-unsaturated esters8
Base used in an attempt to produce higherly reactive no-carrier-added fluoride for labeling of radiopharmaceuticals1 and used in the synthesis of monomeric alumatranes2Deprotonation agent used to study the nucleophilic reactivities of benzenesulfonyl-substituted carbanions3Catalyst involved in:
• Synthesis of polymer-supported proazaphosphatranes for catalysis of amidation and transesterification reactions4
• Wadsworth-Emmons reactions5
• Mukaiyama aldol reactions6
• Synthesis of aryl alcohols via addition reactions7
Packaging
1, 5 g in glass bottle