Methylphosphinic acid

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

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)

gollark: I think you're confusing a bunch of things right now. Or possibly just two things, many worlds and extra spatial dimensions.

gollark: "We"?

gollark: ???

gollark: Things which extend into those instead of just having a constant fixed position in said new spatial dimension are also not going to somehow stop being subject to time, unless the laws of physics privilege it somehow, which would be really weird.

gollark: For one thing, if you add extra spatial dimensions to our universe on top of the existing 3, it isn't suddenly going to gain multiverses or something; ignoring all the complex physics things I'm not aware of which are probably sensitive to this, it will just be another direction in which you can move, perpendicular to the other 3.

References

A. W. Hofman (1872). "New Researches on the Phosphorus Bases". The Chemical News and Journal of Industrial Science: 245–246.
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.
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.
"Process for the preparation of halo-methylphosphinic acid halides". 30 November 1973.
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.
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.
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.
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.
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.

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

[1] A. W. Hofman (1872). "New Researches on the Phosphorus Bases". The Chemical News and Journal of Industrial Science: 245–246.

[geiss-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.

[wat-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.

[grel-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.