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79417

Sigma-Aldrich

Phosphazene base P2-Et

≥98.0% (NT)

Synonym(s):

1-Ethyl-2,2,4,4,4-pentakis(dimethylamino)-2λ5,4λ5-catenadi(phosphazene), Tetramethyl(tris(dimethylamino)phosphoranylidene)phosphorictriamid-Et-imin

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About This Item

Linear Formula:
[(CH3)2N]3P=NP(=NC2H5)[N(CH3)2]2
CAS Number:
165535-45-5
Molecular Weight:
339.40
Beilstein:
7485991
MDL number:
MFCD00145113
UNSPSC Code:
12352000
PubChem Substance ID:
57652793
NACRES:
NA.22

Assay

≥98.0% (NT)

form

liquid

refractive index

n20/D 1.492 (lit.)
n20/D 1.492

bp

96 °C/0.05 mmHg (lit.)

density

1.02 g/mL at 25 °C (lit.)

functional group

amine

SMILES string

CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C

InChI

1S/C12H35N7P2/c1-12-13-20(15(2)3,16(4)5)14-21(17(6)7,18(8)9)19(10)11/h12H2,1-11H3

InChI key

CFUKEHPEQCSIOM-UHFFFAOYSA-N

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Application

Phosphazene Bases: a Family of Extremely Strong, Non-Ionic, Non-Charged Nitrogen–Bases
Phosphazene base P2-Et is an extremely strong, neutral nitrogen base. It gives excellent results where other bases fail

This strong non-ionic base has the ability to catalyze a wide variety of organic transformations such as:
  • Palladium-catalyzed cross-coupling reactions when used in combination with tBuXPhos or tBuBrettPhos G3 precatalysts.
  • Deprotonation of ortho-halobenzyl sulfones to generate α-sulfonyl benzylic carbanions.
  • Conversion of vinyl sufone to allyl sulfone.
  • α-Alkylation of 2-phenyl-2-oxazoline-4-carbonylcamphorsultam in the presence of tetrabutylammonium bromide.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM0873
BCCK6978
BCCD3794
BCCC8814
BCBV0532

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S.H. Kim et al.
Tetrahedron Letters, 36, 4537-4537 (1995)
Enantioselective synthetic method for α-alkylserine via phase-transfer catalytic alkylation of 2-phenyl-2-oxazoline-4-carbonylcamphorsultam.
Lee J, et al.
The Journal of Organic Chemistry, 70(10), 4158-4161 (2005)
P2Et Phosphazene: A Mild, Functional Group Tolerant Base for Soluble, Room Temperature Pd-Catalyzed C?N, C?O, and C?C Cross-Coupling Reactions.
Buitrago S A, et al.
Organic Letters, 17(13), 3370-3373 (2015)
P2-Et-mediated deprotonation of ortho-halobenzyl sulfones: synthetic applications as zwitterionic synthons.
Costa A, et al.
Synlett, 2001(12), 1881-1884 (2001)
Phosphazene base P2-Et mediated isomerization of vinyl sulfones to allyl sulfones.
Jin Z, et al.
Tetrahedron Letters, 37(30), 5247-5248 (1996)

Articles

Phosphazene Bases

Phosphazene base reagents are available as monomeric (P1 and BEMP), dimeric (P2), and tetrameric (P4) bases with different side chains to control their sterical hindrance.

Phosphazene Bases

Phosphazene base reagents are available as monomeric (P1 and BEMP), dimeric (P2), and tetrameric (P4) bases with different side chains to control their sterical hindrance.

Phosphazene Bases

Phosphazene base reagents are available as monomeric (P1 and BEMP), dimeric (P2), and tetrameric (P4) bases with different side chains to control their sterical hindrance.

Phosphazene Bases

Phosphazene base reagents are available as monomeric (P1 and BEMP), dimeric (P2), and tetrameric (P4) bases with different side chains to control their sterical hindrance.

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