Methylphosphinic acid

Methylphosphinic acid is a monobasic acid, the simplest of the phosphinic acids. A central phosphorus atom is connected to a hydroxy group, a hydrogen atom, a methyl group and an oxygen. Derivatives of methylphosphinic acid can have the phosphorus connected hydrogen atom replaced by other organic groups. In early days what is now called methylphosphonic acid was also called methylphosphinic acid.[1]

Methylphosphinic acid
Identifiers
3D model (JSmol)
ChemSpider
DrugBank
ECHA InfoCard 100.021.933
EC Number
  • 224-125-7
Properties
CH5O2P
Molar mass 80.023 g·mol−1
Related compounds
Related compounds
 dimethylphosphinic acid
methylphosphonic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Production

Hydrolysis of methyldichlorophosphine yields methylphosphinic acid.[2] Esters can be produced by reacting with an alcohol instead of water.[2]

Methylphosphinic acid is produced when some binary chemical agent precursors are neutralized.[3][4]

Properties

Rat oral LD50 value for methylphosphinic acid is 940 mg/kg.[3]

Derivatives
  • (1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic acid TPMPA
  • N-methylaminomethane-P-methylphosphinic acid[5] or N-methylamino-methyl-methylphosphinic acid[6]
  • Ethane-1,2-diylbis(methylphosphinic acid)[7]
  • (3-amino-2-hydroxypropyl)methylphosphinic acid
  • Methylphosphinic acid ethyl ester (CAS number 16391-07-4)
  • dimethylphosphoryloxy-methylphosphinic acid
  • N,N-dimethylaminomethane-P-methylphosphinic acid[5]
  • (Aminomethyl)methylphosphinic acid 15901-11-8
  • (2-aminobenzyl)-methylphosphinic acid[8]
  • (6-amino-3-ethyl-1H-benzimidazol-3-ium-2-yl)-methylphosphinic acid
  • [(2S,3S)-3-(methoxymethyl)pentan-2-yl]oxy-methylphosphinic acid
  • (3-Aminocyclopentyl)methylphosphinic acid[9]
  • methylene-di(methylphosphinic acid)

References
  1. A. W. Hofman (1872). "New Researches on the Phosphorus Bases". The Chemical News and Journal of Industrial Science: 245–246.
  2. Geissbühler, H.; Brooks, G. T.; Kearney, P. C. (2013). Synthesis of Pesticides Chemical Structure and Biological Activity Natural Products with Biological Activity: Symposia Papers Presented at the Fourth International Congress of Pesticide Chemistry, Zurich, Switzerland, July 24-28, 1978. Elsevier. p. 114. ISBN 9781483278513.
  3. Watson, Rebecca E.; Hafez, Ahmed M.; Kremsky, Jonathan N.; Bizzigotti, George O. (December 2016). "Toxicity of Binary Chemical Munition Destruction Products: Methylphosphonic Acid, Methylphosphinic Acid, 2-Diisopropylaminoethanol, DF Neutralent, and QL Neutralent". International Journal of Toxicology. 26 (6): 503–512. doi:10.1080/10915810701707551.
  4. "Process for the preparation of halo-methylphosphinic acid halides". 30 November 1973.
  5. Grela, Ewa; Dziełak, Anna; Szydłowska, Katarzyna; Mucha, Artur; Kafarski, Paweł; Grabowiecka, Agnieszka Monika (18 October 2016). "Whole-cell Proteus mirabilis urease inhibition by aminophosphinates for the control of struvite formation". Journal of Medical Microbiology. 65 (10): 1123–1129. doi:10.1099/jmm.0.000342.
  6. Maier, Ludwig (October 1991). "ORGANIC PHOSPHORUS COMPOUNDS 98. SYNTHESIS AND PROPERTIES OF N-METHYLAMINOMETHYLPHOSPHONIC ACID AND DERIVATIVES". Phosphorus, Sulfur, and Silicon and the Related Elements. 62 (1–4): 29–34. doi:10.1080/10426509108034455.
  7. Reiss, Guido J.; Engel, Judith S. (9 January 2008). "Ethane-1,2-diylbis(methylphosphinic acid)". Acta Crystallographica Section E. 64 (2): o400–o400. doi:10.1107/S1600536807068122. PMC 2960156. PMID 21201428.
  8. Collins, DJ; Drygala, PF; Swan, JM (1983). "Organophosphorus compounds. XIX. Synthesis of 2,3-Dihydro-1 H-1,2-benzazaphosphole 2-oxides, variously substituted on nitrogen and phosphorus, by N-P cyclization of zwitterionic intermediates". Australian Journal of Chemistry. 36 (12): 2517. doi:10.1071/CH9832517.
  9. Chebib, Mary; Hanrahan, Jane R.; Kumar, Rohan J.; Mewett, Kenneth N.; Morriss, Gwendolyn; Wooller, Soraya; Johnston, Graham A.R. (March 2007). "(3-Aminocyclopentyl)methylphosphinic acids: Novel GABAC receptor antagonists". Neuropharmacology. 52 (3): 779–787. doi:10.1016/j.neuropharm.2006.09.014.
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