809551
Methyltriphenylphosphonium methylcarbonate
Synonym(s):
Perosa-Selva-Noè Vinylation Reagent
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About This Item
Empirical Formula (Hill Notation):
C21H21O3P
CAS Number:
Molecular Weight:
352.36
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22
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
form
powder
reaction suitability
reaction type: C-C Bond Formation
mp
146-151 °C
functional group
phosphine
storage temp.
2-8°C
Quality Level
Related Categories
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).
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Methyltriphenylphosphonium Methylcarbonate, an All-In-One Wittig Vinylation Reagent.
Cattelan L, et al.
ChemSusChem, 8(23), 3963-3966 (2015)
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