Methylphosphinic acid

Methylphosphinic acid

Names
Preferred IUPAC name Methylphosphinic acid
Identifiers
CAS Number	4206-94-4
3D model (JSmol)	Interactive image
ChemSpider	10450135
DrugBank	DB02845
ECHA InfoCard	100.021.933
EC Number	224-125-7
PubChem CID	3396560
CompTox Dashboard (EPA)	DTXSID30871063
InChI InChI=1S/CH5O2P/c1-4(2)3/h4H,1H3,(H,2,3) Key: BCDIWLCKOCHCIH-UHFFFAOYSA-N
SMILES CP(=O)O
Properties
Chemical formula	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

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]

Production

Methylphosphinic acid can be produced by the hydrolysis of dimethyl methylphosphonate, which is conveniently obtained from trimethylphosphite. ^[2]

Hydrolysis of methyldichlorophosphine yields methylphosphinic acid, ^[3]

Methylphosphinic acid is a common byproduct of the hydrolysis of various CH₃P-containing esters and amides, as occur in pesticides for example. ^{[4] [5]}

Properties

Rat oral LD₅₀ value for methylphosphinic acid is 940 mg/kg. ^[4]

Derivatives

• (1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic acid TPMPA
• N-methylaminomethane-P-methylphosphinic acid ^[6] or N-methylamino-methyl-methylphosphinic acid ^[7]
• Ethane-1,2-diylbis(methylphosphinic acid) ^[8]
• (3-amino-2-hydroxypropyl)methylphosphinic acid
• Methylphosphinic acid ethyl ester (CAS number 16391-07-4)
• dimethylphosphoryloxy-methylphosphinic acid
• N,N-dimethylaminomethane-P-methylphosphinic acid ^[6]
• (Aminomethyl)methylphosphinic acid 15901-11-8
• (2-aminobenzyl)-methylphosphinic acid ^[9]
• (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 ^[10]
• 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. Crofts, Peter C.; Kosolapoff, Gennady M. (1953). "Preparation and Determination of Apparent Dissociation Constants of Some Alkylphosphonic and Dialkylphosphinic Acids1". Journal of the American Chemical Society. 75 (14): 3379–3383. Bibcode:1953JAChS..75.3379C. doi:10.1021/ja01110a024.
3. 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.
4. 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 . PMID   18066966. S2CID   8372615.
5. "Process for the preparation of halo-methylphosphinic acid halides". 30 November 1973.
6. 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. PMID   27550502.
7. Maier, Ludwig (October 1991). "Organic Phosphorus Compounds 98.1Synthesis 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.
8. Reiss, Guido J.; Engel, Judith S. (9 January 2008). "Ethane-1,2-diylbis(methylphosphinic acid)". Acta Crystallographica Section E. 64 (2): o400. Bibcode:2008AcCrE..64O.400R. doi:10.1107/S1600536807068122. PMC   2960156 . PMID   21201428.
9. 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.
10. 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. PMID   17098260. S2CID   15100966.