Methylphosphonic acid

Methylphosphonic acid
Identifiers

CAS Number	993-13-5
3D model (Jmol)	Interactive image
ChEBI	CHEBI:45129
ChemSpider	13220
ECHA InfoCard	100.012.370
EC Number	213-607-2
KEGG	C20396
MeSH	C032627
PubChem	13818
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

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). Retrieved 12 December 2013.

Organophosphorus

Only P-O bonds

P(III)	Phosphite/Organophosphite

P(V)	Phosphate/Organophosphate

With P-C bonds

One P-C bonds

P(III)	Phosphonite

P(V)	Phosphonate

Two P-C bonds

P(III)	Phosphinite

P(V)	Phosphinate

Three P-C bonds

P(III)	Phosphine

P(V)	Phosphine oxide

With P-N bonds

One P-N bond

P(III)	Phosphoramidite e.g. Nucleoside phosphoramidite

P(V)	Phosphoramidate e.g. Phosphocreatine

Two P-N bond

P(III)	Phosphorodiamidite

P(V)	Phosphorodiamidate e.g. Morpholino Cyclophosphamide

Three P-N bond

P(V)	Phosphoramide e.g. Hexamethylphosphoramide Metepa

With P-C and P-N bonds

One P-C bond and one P-N bond

P(V)	Phosphonamidate

One P-C bond and two P-N bond

P(V)	Phosphonamide

Two P-C bond and one P-N bond

P(V)	Phosphinamide

With P-S bonds

One P-S bond

P(III)	Phosphorothioite

P(V)	Phosphorothioate

Two P-S bond

P(III)	Phosphorodithioite

P(V)	Phosphorodithioate

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