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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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1 ML
$138.00
5 ML
$441.00
25 ML
$1,510.00

$138.00

Available to ship onApril 24, 2025Details

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1 ML
$138.00
5 ML
$441.00
25 ML
$1,510.00

About This Item

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

$138.00

Available to ship onApril 24, 2025Details

Request a Bulk Order

form

liquid

Quality Level

100

concentration

~0.8 M in hexane

density

0.850-0.875 g/mL at 20 °C

functional group

amine

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

Related Categories

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 agentscitationcitation; Base for enolate formation and stereoselective alkylationcitation
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[1][2]; Base for enolate formation and stereoselective alkylation[3]

signalword

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

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-14.8 °F - closed cup

flash_point_c

-26 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK9678
BCCL9781
BCCK1923
BCCH3719
BCCF9298

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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.

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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