809551

Methyltriphenylphosphonium methylcarbonate

• Synonym(s): Perosa-Selva-Noè Vinylation Reagent
• Empirical Formula (Hill Notation): C₂₁H₂₁O₃P
• CAS Number: 1067966-63-5
• Molecular Weight: 352.36
• UNSPSC Code: 12352108
• PubChem Substance ID: 329769168
• NACRES: NA.22

Properties

• 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).

Other Notes

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

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable