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761060

(Tributylphosphoranylidene)acetonitrile

Name: (Tributylphosphoranylidene)acetonitrile
Brand: ALDRICH

97%

Synonym(s):

(Cyanomethylene)tributylphosphorane

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About This Item

Empirical Formula (Hill Notation):

C₁₄H₂₈NP

CAS Number:

157141-27-0

Molecular Weight:

241.35

MDL number:

MFCD01321151

UNSPSC Code:

12352000

NACRES:

NA.22

Assay:

97%

Form:

liquid

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Properties

assay

97%

form

liquid

refractive index

n20/D 1.500 (lit.)

density

0.921 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

[P](=CC#N)(CCCC)(CCCC)CCCC

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

InChI key

OZMLUMPWPFZWTP-UHFFFAOYSA-N

Description

General description

(Tributylphosphoranylidene)acetonitrile or cyanomethylenetrimethylphosphorane (Bu₃P=CHCN) is a Wittig reagent employed in the transformation of the carbonyl compounds, including aldehydes, esters, and lactones into the corresponding unsaturated nitriles.

Application

(Tributylphosphoranylidene)acetonitrile can be utilized as a reagent in the:

Stereoselective synthesis of skytanthine and other O- and N-containing heterocycles by Mitsunobu intramolecular cycloalkylation.
Wittig olefination of esters, lactones, N-Boc lactam, and cyclic imide to corresponding Wittig products.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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(Tributylphosphoranylidene) acetonitrile

Wyatt, Peter B

Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)

Formation of heterocycles by the Mitsunobu reaction. Stereoselective synthesis of (+)-α-skytanthine

Tsunoda T, et al.

Tetrahedron Letters, 37(14), 2463-2466 (1996)

Cyanomethylenetrimethylphosphorane, a powerful reagent for the Wittig olefination of esters, lactones and imides