Methylarsonic acid
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| Names | |
|---|---|
| Preferred IUPAC name
Methylarsonic acid[1] | |
| Other names
Methanearsonic acid Monomethylarsonic acid | |
| Identifiers | |
3D model (JSmol) |
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| 4-04-00-03682 | |
| ChemSpider | |
| ECHA InfoCard | 100.004.278 |
| EC Number |
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PubChem CID |
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| RTECS number |
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| UNII | |
| UN number | 1557 |
CompTox Dashboard (EPA) |
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| Properties | |
| 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).
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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 (DSMA), have been widely used as herbicides and fungicides for cotton and rice.[2]
Reactions
[edit]At physiological pH, methylarsonic acid exists mainly as the monoanion CH3AsO3H−; the dianion CH
3AsO2−
3 predominates above about pH 9.
Synthesis and biosynthesis
[edit]Reaction of sodium arsenite with methyl iodide gives methylarsonic acid. This historically significant conversion is called the Meyer reaction:[3]
- NaAsO(OH)2 + CH3I → CH3AsO(OH)2 + NaI
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 inorganic trivalent arsenic is thought to begin with its conversion to methylarsonate, with S-adenosylmethionine as the methyl donor. Methylarsonates are the precursors to cacodylates by reduction (to methylarsonous acid) followed by a second methylation.[4]
Safety
[edit]Methylarsonic acid is much less toxic than inorganic arsenic, but its metabolite methylarsonous acid is highly toxic.[4]
References
[edit]- ↑ 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. ISBN 978-3-527-30673-2.
- ↑ G. Meyer (1883). "Ueber einige anomale Reaktionen". Berichte der deutschen chemischen Gesellschaft. 16: 1439–1443. doi:10.1002/cber.188301601316.
- 1 2 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.