Methylating with a pesticide?

[Nicodem]

OK, I know this question seams crazy, but did anybody considered (or tried) using a pesticide called “dichlorvos” as a methylation reagent?

Dichlorvos structure: (MeO)₂PO-O-CH=CCl₂     

http://www.alanwood.net/pesticides/dichlorvos.html

Synonyms:

http://www.cdc.gov/niosh/rtecs/tc55730.html#L

Toxicology and other info:

http://www.inchem.org/documents/pds/pds/pest2_e.htm

One of the preparations (Nogos^TM) is a 50% solution in xylene which is just perfect.

Yeah, I know it’s a pesticide but it would still be much safer than dimethyl sulphate since it is not that toxic to humans. Trimethyl phosphate seams to work satisfactorily as a methylation reagent so I see only few reasons why this dimethyl dichlorovinyl phosphate would not.

One problem I see is that it would probably not work with plain phenols like p-MeO-phenol since there is danger of its condensation with the reactive dichloroacetaldehyde which would form from the reagent degradation. But I think it might work with hydroxy benzaldehydes like syringaldehyde, 2-hydroxy-5-MeO-benzaldehyde and similar, ring enough deactivated, compounds.

The other problem is that the dichlorovinyl group might bee the first to hydrolyze, leaving the much less or non effective (MeO)₂HPO₂. Maybe it would nevertheless work if used in the melt phase like in

https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html

though I'm concerned it might form O-blocked phenols of the type Ar-O-CH=CCl₂ in the absence of water.

But if the dichlorovinyl group is truly the best leaving group it should bee possible to solvatize/transesterify dichlorvos in refluxing methanol yielding (MeO)₃PO and Cl₂C-CH(OMe)₂. Maybe this mixture could bee used directly as a methylenation agent without even separating the dichloroacetaldehyde dimethylacetal out?

Sorry if somebee finds this stupid. I’m just playing with the thought of a “ready to use” OTC methylation reagent.