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79421

Sigma-Aldrich

Phosphazene base P4-t-Bu solution

~0.8 M in hexane

Synonym(s):

1-tert-Butyl-4,4,4-tris(dimethylamino)-2,2-bis[tris(dimethylamino)-phosphoranylidenamino]-2λ5,4λ5-catenadi(phosphazene)

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About This Item

Empirical Formula (Hill Notation):
C22H63N13P4
CAS Number:
111324-04-0
Molecular Weight:
633.72
Beilstein:
5784423
MDL number:
MFCD00145114
UNSPSC Code:
12352001
PubChem Substance ID:
57652794
NACRES:
NA.22

form

liquid

concentration

~0.8 M in hexane

density

0.850-0.875 g/mL at 20 °C

SMILES string

CN(C)P(=NP(=NC(C)(C)C)(N=P(N(C)C)(N(C)C)N(C)C)N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C

InChI

1S/C22H63N13P4/c1-22(2,3)23-36(24-37(27(4)5,28(6)7)29(8)9,25-38(30(10)11,31(12)13)32(14)15)26-39(33(16)17,34(18)19)35(20)21/h1-21H3

InChI key

NSRBCQCXZAYQHF-UHFFFAOYSA-N

Application

Phosphazene Bases: a Family of Extremely Strong, Non-Ionic, Non-Charged Nitrogen–Bases

Caution

Product crystallizes out of solution, can be redissolved on heating to 40°C.

Other Notes

Extremely strong, hindered, neutral nitrogen base; it is about 1018 times more basic than DBU [pKa (DMSO) 30.25]. Stable to hydrolysis and unaffected by alkylating agents; Base for enolate formation and stereoselective alkylation

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 1 Inhalation - STOT SE 3

Target Organs

Central nervous system, Nervous system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-14.8 °F - closed cup

Flash Point(C)

-26 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A. Solladie-Cavallo et al.
Tetrahedron Letters, 43, 415-415 (2002)
Saurabh Mehta et al.
The Journal of organic chemistry, 84(9), 5492-5503 (2019-04-16)
Phosphazene superbase P4- t-Bu mediated iodoaminocyclization of 2-(1-alkynyl)benzamides is reported. The reaction works under ambient conditions and instantaneously results in the synthesis of isoindolin-1-ones in 65-97% yields, in a regio- and stereoselective manner. The exclusive formation of products with Z-geometry
H.T. Mamdani, R.C. Hartley
Tetrahedron Letters, 41, 7417-7417 (2000)
George A Kraus et al.
Bioorganic & medicinal chemistry letters, 19(19), 5539-5542 (2009-09-05)
Dihydroindolo[2,1-a]isoquinolines were synthesized from tetrahydroisoquinolines and alpha-fluoroaldehydes by a novel two-step procedure. These compounds exhibited significant immunosuppressive activity against IL-2, IL-10 and IFN-gamma.
R. Schwesinger et al
Angewandte Chemie (International Edition in English), 105, 1420-1420 (1993)

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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