Methylphosphonic acid

Methylphosphonic acid
Identifiers
CAS Number	993-13-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:45129;
ChemSpider	13220;
ECHA InfoCard	100.012.370
EC Number	213-607-2;
KEGG	C20396;
MeSH	C032627
PubChem CID	13818;
UNII	329W4YM10Z ;
CompTox Dashboard (EPA)	DTXSID5047748 ;
	InChI InChI=1S/CH5O3P/c1-5(2,3)4/h1H3,(H2,2,3,4) Key: YACKEPLHDIMKIO-UHFFFAOYSA-N; InChI=1/CH5O3P/c1-5(2,3)4/h1H3,(H2,2,3,4) Key: YACKEPLHDIMKIO-UHFFFAOYAB;
	SMILES CP(=O)(O)O;
Properties
Chemical formula	CH5O3P
Molar mass	96.02
Appearance	White Solid
Melting point	105 to 107 °C (221 to 225 °F; 378 to 380 K)[1]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Methylphosphonic acid is an organophosphorus compound with the chemical formula. CH₃P(O)(OH)₂. The phosphorus center is tetrahedral and is bonded to a methyl group, two OH groups and an oxygen. Methylphosphonic acid is a white, non-volatile solid that is poorly soluble in organic solvent but soluble in water and common alcohols.[2]

Preparation

Methylphosphonic acid can be prepared via the Michaelis-Arbuzov reaction from triethylphosphite:[3]

CH₃Cl + P(OC₂H₅)₃ → CH₃PO(OC₂H₅)₂ + C₂H₅Cl

The dialkylphosphonate is then treated with chlorotrimethylsilane:

CH₃PO(OC₂H₅)₂ + 2 Me₃SiCl → CH₃PO(OSiMe₃)₂ + 2 C₂H₅Cl

The siloxyphosphinate is then hydrolyzed:

CH₃PO(OSiMe₃)₂ + 2H₂O → CH₃PO(OH)₂ + 2 HOSiMe₃

gollark: And implies that telling people it's bad would somehow detract from dealing with it, even though it would probably be the other way round.

gollark: This analogy requires that Trump also be actually dealing with it well at the same time.

gollark: ???

gollark: I don't know about *intent*, but I don't agree with it.

gollark: It's very uncool to claim that a very bad thing is totally fine.

References

"Methylphosphonic Acid". Sigma-Aldrich. Retrieved 12 December 2013.
"methylphosphonic acid - Compound Summary". NCBI. Retrieved 12 December 2013.
Katritzky, Pilarski, Alan, Boguslaw. "A One-Pot Procedure For the Preparation of Phosphonic Acids From Alkyl Halides" (PDF). Archived from the original (PDF) on 23 September 2015. Retrieved 12 December 2013.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] "Methylphosphonic Acid". Sigma-Aldrich. Retrieved 12 December 2013.

[2] "methylphosphonic acid - Compound Summary". NCBI. Retrieved 12 December 2013.

[3] Katritzky, Pilarski, Alan, Boguslaw. "A One-Pot Procedure For the Preparation of Phosphonic Acids From Alkyl Halides" (PDF). Archived from the original (PDF) on 23 September 2015. Retrieved 12 December 2013.