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Safety Information

761060

Sigma-Aldrich

(Tributylphosphoranylidene)acetonitrile

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
UNSPSC Code:
12352000
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.500 (lit.)

density

0.921 g/mL at 25 °C

storage temp.

2-8°C

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

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

JAN Code

761060-VAR:
761060-1G:4548173319551
761060-500MG:4548173319568
761060-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL5715
MKCL4453
MKCD4647
MKCB8261
MKBK3789

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Formation of heterocycles by the Mitsunobu reaction. Stereoselective synthesis of (+)-α-skytanthine
Tsunoda T, et al.
Tetrahedron Letters, 37(14), 2463-2466 (1996)
(Tributylphosphoranylidene) acetonitrile
Wyatt, Peter B
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Cyanomethylenetrimethylphosphorane, a powerful reagent for the Wittig olefination of esters, lactones and imides
Tsunoda T, et al.
Tetrahedron Letters, 41(2), 235-237 (2000)

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