Cacodylic acid

Cacodylic acid
IUPAC name Dimethylarsinic acid
Other names Dimethylarsenic acid, Cacodylic acid, Hydroxydimethylarsine oxide, Arsecodile, Ansar, Silvisar, Phytar 560, DMAA, UN 1572
Identifiers
CAS number	75-60-5 Y
PubChem	2513
ChemSpider	2418 Y
UNII	AJ2HL7EU8K Y
EC number	200-883-4
DrugBank	DB02994
KEGG	C07308 Y
ChEBI	CHEBI:29839 Y
RTECS number	CH7525000
Jmol-3D images	Image 1
SMILES O=[As](O)(C)C
InChI InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5) Y Key: OGGXGZAMXPVRFZ-UHFFFAOYSA-N Y InChI=1/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5) Key: OGGXGZAMXPVRFZ-UHFFFAOYAP
Properties
Molecular formula	C2H7AsO2
Molar mass	137.9977 g/mol
Appearance	White crystals or powder
Density	> 1.1 g/cm3
Melting point	192 - 198 °C
Boiling point	> 200 °C
Solubility in water	667 g/l
Acidity (pKa)	6.3
Hazards
MSDS	External MSDS
EU classification	T+
R-phrases	R26/27/28, R40
Y acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cacodylic acid is the chemical compound with the formula (CH₃)₂AsO₂H. Derivatives of cacodylic acid, cacodylates, were frequently used as herbicides. For example, "Agent Blue," one of the chemicals used during the Vietnam War, is a mixture of cacodylic acid and sodium cacodylate. Sodium cacodylate is frequently used as a buffering agent in the preparation and fixation of biological samples for electron microscopy.

History

Significant early research into cacodyls was done by Robert Bunsen at the University of Marburg. Bunsen said of the compounds, "the smell of this body produces instantaneous tingling of the hands and feet, and even giddiness and insensibility...It is remarkable that when one is exposed to the smell of these compounds the tongue becomes covered with a black coating, even when no further evil effects are noticeable". His work in this field led to an increased understanding of the methyl radical.

Cacodyloxide, ((CH₃)₂As)₂O, is often considered the first organometallic compound to be prepared synthetically.

Synthesis and reactions

In the 18th century it was known that combining As₂O₃ and four equivalents of potassium acetate (CH₃CO₂K) gives a product called "Cadet's fuming liquid" which contains cacodyl oxide, ((CH₃)₂As)₂O and cacodyl, ((CH₃)₂As).

Cacodylic acid can be reduced to dimethylarsine (III) derivatives, which are versatile intermediates for the synthesis of other organoarsenic compounds:^[1][2]

(CH₃)₂AsO₂H + 2 Zn + 4 HCl → (CH₃)₂AsH + 2 ZnCl₂ + 2 H₂O

(CH₃)₂AsO₂H + SO₂ + HI → (CH₃)₂AsI + SO₃ + H₂O

Health effects

Cacodylic acid is highly toxic by ingestion, inhalation, or skin contact. Once thought to be a byproduct of inorganic arsenic detoxification, it is now believed to have serious health consequences of its own. It has been shown to be teratogenic in rodents, most often causing cleft palate but also fetal fatality at high doses. It has been shown to be genotoxic in human cells, causing apoptosis and also decreased DNA production and shorter DNA strands. While not itself a strong carcinogen, cacodylic acid does promote tumors in the presence of carcinogens in organs such as the kidneys and liver.

See also

• Arsenic
• Arsine
• Cacodyl oxide

References

1. ^ Feltham, R. D.; Kasenally, A. and Nyholm, R. S., "A New Synthesis of Di- and Tri-Tertiary Arsines", Journal of Organometallic Chemistry, 1967, volume 7, 285-288.
2. ^ Burrows, G. J. and Turner, E. E., "A New Type of Compound containing Arsenic", Journal of the Chemical Society Transactions, 1920, 1374-1383

• Kenyon, E. M.; Hughes, M. F. (2001). "A Concise Review of the Toxicity and Carcinogenicity of Dimethylarsenic Acid". Toxicology 160 (1-3): 227–236. doi:10.1016/S0300-483X(00)00458-3. 
• Elschenbroich, C; Salzer, A. (1992) Organometallics, 2nd Edition
• Bunsen Biography

External links

• Case Studies in Environmental Medicine - Arsenic Toxicity