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809551 Sigma-Aldrich

Methyltriphenylphosphonium methylcarbonate

Synonym: Perosa-Selva-Noè Vinylation Reagent

  • CAS Number 1067966-63-5

  • Empirical Formula (Hill Notation) C21H21O3P

  • Molecular Weight 352.36

  •  PubChem Substance ID 329769168

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Properties

Related Categories C-C Bond Formation, Chemical Synthesis, Olefination, Synthetic Reagents, Wittig Reagents More...
form   powder
reaction suitability   reaction type: C-C Bond Formation
mp   146-151 °C
storage temp.   2-8°C
SMILES string   C[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[O-]C(OC)=O
InChI   1S/C19H18P.C2H4O3/c1-20(17-11-5-2-6-12-17,18-13-7-3-8-14-18)19-15-9-4-10-16-19;1-5-2(3)4/h2-16H,1H3;1H3,(H,3,4)/q+1;/p-1
InChI key   FALLFMKOBMQQNQ-UHFFFAOYSA-M

Description

General description

Methyltriphenylphosphonium methylcarbonate, also known as Perosa-Selva-Noè vinylation reagent, is a green reagent for performing halide and base-free Wittig reaction. It can be prepared by reacting triphenylphosphine with dimethylcarbonate.

Application

[Ph3PCH3][CH3OCO2] is a latent ylide that promotes Wittig vinylation of aldehydes and ketones. Alkenes are obtained simply by mixing [Ph3PCH3][CH3OCO2] and the carbonyl and heating in a solvent (no base, no halides, and no inorganic byproducts needed).

Packaging

5 g in glass bottle

Other Notes

Methyltriphenylphosphonium Methylcarbonate, an All-In-One Wittig Vinylation Reagent

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
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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