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761060 Sigma-Aldrich

(Tributylphosphoranylidene)acetonitrile

97%

Synonym: (Cyanomethylene)tributylphosphorane

  • CAS Number 157141-27-0

  • Empirical Formula (Hill Notation) C14H28NP

  • Molecular Weight 241.35

  •  NACRES NA.22

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Properties

Related Categories C-X Bond Formation (Non-Halogen), Chemical Synthesis, Mitsunobu, Synthetic Reagents
Quality Level   100
assay   97%
refractive index   n20/D 1.500 (lit.)
density   0.921 g/mL at 25 °C
storage temp.   2-8°C

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.

Packaging

1 g in glass bottle

500 mg in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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