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556955

Sigma-Aldrich

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

Synonym(s):

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

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About This Item

Linear Formula:
PN(CH(CH3)2)CH2CH2NCH2CH2N(CH(CH3)2)(CH2CH2N(CH(CH3)2))
CAS Number:
175845-21-3
Molecular Weight:
300.42
MDL number:
MFCD03701530
UNSPSC Code:
12352005
PubChem Substance ID:
24879596
NACRES:
NA.22

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

Related Categories

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

185.0 °F - closed cup

Flash Point(C)

85 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP1209
MKCP1210
MKCJ8804
MKCF1493
MKBT9367V

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Wadhwa, K.; Verkade, J. G.
The Journal of Organic Chemistry, ASAP-ASAP (2009)

Articles

Proazaphosphatranes: Verkade’s Superbases

Proazaphosphatranes: Verkade’s Superbases

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