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752959

Sigma-Aldrich

(Tributylphosphoranylidene)acetonitrile solution

1 M in toluene

Synonym(e):

CMBP solution, Tsunoda reagent, Cyanomethylene)tributylphosphorane

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1 ML
CHF 113.00
5 ML
CHF 343.00

CHF 113.00

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1 ML
CHF 113.00
5 ML
CHF 343.00

About This Item

Empirische Formel (Hill-System):
C14H28NP
Molekulargewicht:
241.35
MDL-Nummer:
MFCD01321151
UNSPSC-Code:
12352001
PubChem Substanz-ID:
329766327
NACRES:
NA.22

CHF 113.00

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Form

liquid

Qualitätsniveau

100

Konzentration

1 M in toluene

Brechungsindex

n/D 1.500 (lit.)
n20/D 1.501

Dichte

0.886 g/mL at 25 °C

Funktionelle Gruppe

nitrile
phosphine

Lagertemp.

2-8°C

SMILES String

CCCCP(CCCC)(CCCC)=CC#N

InChI

1S/C14H28NP/c1-4-7-11-16(14-10-15,12-8-5-2)13-9-6-3/h14H,4-9,11-13H2,1-3H3

InChIKey

OZMLUMPWPFZWTP-UHFFFAOYSA-N

Allgemeine Beschreibung

(Tributylphosphoranylidene)acetonitrile is a stabilized trialkylphosphorane that can act as a substitute to the diethyl azodicarboxylate and triphenylphosphine (DEAD-TPP) system for Mitsunobu reaction between nucleophiles (HA) and alcohols (ROH) to form RA. It is highly useful when the pKa of the nucleophiles are higher than 11.[1][2][3]

Signalwort

Danger

Gefahreneinstufungen

Aquatic Chronic 3 - Asp. Tox. 1 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

Zielorgane

Central nervous system

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 3

Flammpunkt (°F)

44.6 °F - closed cup

Flammpunkt (°C)

7 °C - closed cup

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
MKCW4284
MKCV5260
MKCT6979
MKCT8726
MKCR2618

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p-Toluolsulfonamid ReagentPlus®, ≥99%

Sigma-Aldrich

236330

p-Toluolsulfonamid

Application of Tsunoda Reagent to the Convenient Synthesis of Drug-Like Pyrazoles.
Mosallanejad A
Tetrahedron Letters, 59(18), 1708-1710 (2018)
Novel reactivity of stabilized methylenetributylphosphorane: a new Mitsunobu reagent.
Tsunoda T
Tetrahedron Letters, 35(28), 5081-5082 (1994)
Izumi Sakamoto et al.
Chemical & pharmaceutical bulletin, 53(11), 1508-1509 (2005-11-08)
(Cyanomethylene)tributylphosphorane (CMBP), which promoted the alkylation of various nucleophiles (HA) with alcohols (ROH) to give RA (Mitsunobu-type reaction), was prepared in two steps starting from chloroacetonitrile.

Questions

1–2 of 2 Questions  

  1. 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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  2. 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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