Methylarsonic acid

Methylarsonic acid
Names
	Preferred IUPAC name Methylarsonic acid[1]
	Other names Methanearsonic acid; Monomethylarsonic acid
Identifiers
CAS Number	124-58-3;
3D model (JSmol)	Interactive image;
Beilstein Reference	4-04-00-03682
ChemSpider	8604;
ECHA InfoCard	100.004.278
EC Number	204-705-6;
PubChem CID	8948;
RTECS number	PA1575000;
UNII	J37VJ5709S;
UN number	1557
CompTox Dashboard (EPA)	DTXSID4020903 ;
	InChI InChI=1S/CH5AsO3/c1-2(3,4)5/h1H3,(H2,3,4,5) Key: QYPPRTNMGCREIM-UHFFFAOYSA-N;
	SMILES C[As](=O)(O)O;
Properties
Chemical formula	CH5AsO3
Molar mass	139.970 g·mol−1
Appearance	white solid
Melting point	160.5 °C (320.9 °F; 433.6 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methylarsonic acid is an organoarsenic compound with the formula CH₃AsO₃H₂. It is a colorless, water-soluble solid. Salts of this compound, e.g. disodium methyl arsonate, have been widely used in as herbicides and fungicides in growing cotton and rice.[2]

Reactions

Near physiological pH, methanearsonic acid converts to its conjugate bases, the methylarsonates. These include CH₃AsO₃H⁻ and CH
₃AsO²⁻
₃.

Synthesis and biosynthesis

Reaction of arsenous acid with methyl iodide gives methylarsonic acid. This historically significant conversion is called the Meyer reaction:[3]

As(OH)₃ + CH₃I + NaOH → CH₃AsO(OH)₂ + NaI + H₂O

The then-novel aspect of the reaction was that alkylation occurs at arsenic, leading to oxidation of arsenic from oxidation state +3 to +5.

The biomethylation of arsenic compounds is thought to start with the formation of methanearsonates. Thus, trivalent arsenic compounds are methylated to give methanearsonate. S-Adenosylmethionine is the methyl donor. The methanearsonates are the precursors to cacodylates, again by the cycle of reduction (to methylarsonous acid) followed by a second methylation.[4]

Safety

Like most arsenic compounds, it is highly toxic.[4]

References

International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. pp. 916, 918. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
Grund, S. C.; Hanusch, K.; Wolf, H. U. "Arsenic and Arsenic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_113.pub2.
G. Meyer (1883). "Ueber einige anomale Reaktionen". Berichte der deutschen chemischen Gesellschaft. 13: 1439–1443. doi:10.1002/cber.188301601316.
Styblo, M.; Del Razo, L. M.; Vega, L.; Germolec, D. R.; LeCluyse, E. L.; Hamilton, G. A.; Reed, W.; Wang, C.; Cullen, W. R.; Thomas, D. J. (2000). "Comparative toxicity of trivalent and pentavalent inorganic and methylated arsenicals in rat and human cells". Archives of Toxicology. 74: 289–299. doi:10.1007/s002040000134.

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[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. pp. 916, 918. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[Ullmann-2] Grund, S. C.; Hanusch, K.; Wolf, H. U. "Arsenic and Arsenic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_113.pub2.

[3] G. Meyer (1883). "Ueber einige anomale Reaktionen". Berichte der deutschen chemischen Gesellschaft. 13: 1439–1443. doi:10.1002/cber.188301601316.

[Cullen-4] Styblo, M.; Del Razo, L. M.; Vega, L.; Germolec, D. R.; LeCluyse, E. L.; Hamilton, G. A.; Reed, W.; Wang, C.; Cullen, W. R.; Thomas, D. J. (2000). "Comparative toxicity of trivalent and pentavalent inorganic and methylated arsenicals in rat and human cells". Archives of Toxicology. 74: 289–299. doi:10.1007/s002040000134.