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  • 556955 - 2,8,9-Triisopropyl-2,5,8,9-tetraaza-1-phosphabicyclo[3,3,3]undecane

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556955 Sigma-Aldrich

2,8,9-Triisopropyl-2,5,8,9-tetraaza-1-phosphabicyclo[3,3,3]undecane

Synonym: [2,5,8,9-Tetraaza-1-phosphabicyclo[3.3.3]undecane-2,8,9-tris(1-methylethyl)]

  • CAS Number 175845-21-3

  • Linear Formula PN(CH(CH3)2)CH2CH2NCH2CH2N(CH(CH3)2)(CH2CH2N(CH(CH3)2))

  • Molecular Weight 300.42

  •  MDL number MFCD03701530

  •  PubChem Substance ID 24879596

  •  NACRES NA.22

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Properties

Related Categories Acids & Bases, Bases, Chemical Synthesis, Organic Bases, Synthetic Reagents More...
Quality Level   100
refractive index   n20/D 1.4830 (lit.)
density   0.922 g/mL at 25 °C (lit.)
SMILES string   CC(C)N1CCN2CCN(C(C)C)P1N(CC2)C(C)C
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
InChI key   DFRWCJYSXGNOFD-UHFFFAOYSA-N

Description

Application

Base used in an attempt to produce higherly reactive no-carrier-added fluoride for labeling of radiopharmaceuticals and used in the synthesis of monomeric alumatranes

Deprotonation agent used to study the nucleophilic reactivities of benzenesulfonyl-substituted carbanions

Catalyst involved in:
• Synthesis of polymer-supported proazaphosphatranes for catalysis of amidation and transesterification reactions
• Wadsworth-Emmons reactions
• Mukaiyama aldol reactions
• Synthesis of aryl alcohols via addition reactions

Catalyst used in the synthesis of β-hydroxyesters and α,β-unsaturated esters

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NA 1993 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
closed cup
Flash Point(C) 
closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Proazaphosphatranes: Verkade’s Superbases

Sigma-Aldrich is pleased to offer Verkade’s Superbases. For a recent survey of the applications of proazaphosphatranes in organic synthesis, see Aldrichimica Acta, 2004, 37(1).
ChemFiles Volume 4 Article 2
Keywords: Aldrichimica Acta, Applications, Organic synthesis

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Peer-Reviewed Papers
15

References

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