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Concept
Cacodyl
Summary
Cacodyl, also known as dicacodyl or tetramethyldiarsine, (CH3)2As–As(CH3)2, is an organoarsenic compound that constitutes a major part of "Cadet's fuming liquid" (named after the French chemist Louis Claude Cadet de Gassicourt). It is a poisonous oily liquid with an extremely unpleasant garlicky odor. Cacodyl undergoes spontaneous combustion in dry air.
Cacodyl is also the name of the functional group or radical (CH3)2As.
A mixture of dicacodyl and cacodyl oxide ((CH3)2As–O–As(CH3)2) was first prepared by Cadet by the reaction of potassium acetate with arsenic trioxide. A subsequent reduction yields a mixture of several methylated arsenic compounds including dicacodyl.
The global reaction (mass balance) corresponding to the oxide formation is the following:
A more efficient synthesis was later developed which started from the dimethyl arsine chloride and dimethyl arsine:
Robert Wilhelm Bunsen coined the name kakodyl (later modified to cacodyl in English) for the dimethylarsinyl radical, (CH3)2As, from the Greek κακώδης kakōdēs ("evil-smelling") and ὕλη hylē ("matter").
It was investigated by Edward Frankland and (for over six years) by Robert Bunsen and is considered the earliest organometallic compound ever discovered (even though arsenic is not a true metal).
From it other compounds were made, such as cacodyl fluoride, cacodyl chloride, et cetera. One compound, cacodyl cyanide, was particularly awful. In Bunsen's words "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".
Work on cacodyl led Bunsen to the postulation of "methyl radicals" as part of the then-current radical theory.
Cacodyl was used to try to prove the radical theory of Jöns Jacob Berzelius, which resulted in a wide use of cacodyl in research laboratories. Afterward interest in the toxic, malodorous compound decreased.
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Organoarsenic chemistry
Organoarsenic chemistry is the chemistry of compounds containing a chemical bond between arsenic and carbon. A few organoarsenic compounds, also called "organoarsenicals," are produced industrially with uses as insecticides, herbicides, and fungicides. In general these applications are declining in step with growing concerns about their impact on the environment and human health. The parent compounds are arsane and arsenic acid. Despite their toxicity, organoarsenic biomolecules are well known.
Cadet's fuming liquid
Cadet's fuming liquid was a red-brown oily liquid prepared in 1760 by the French chemist Louis Claude Cadet de Gassicourt (1731-1799) by the reaction of potassium acetate with arsenic trioxide. It consisted mostly of dicacodyl (((CH3)2As)2) and cacodyl oxide (((CH3)2As)2O). The global reaction (mass balance) corresponding to the oxide formation is the following: These were the first organometallic substances prepared; as such, Cadet has been regarded as the father of organometallic chemistry.
Cacodylic acid
Cacodylic acid is an organoarsenic compound with the formula (CH3)2AsO2H. With the formula R2As(O)OH, it is the simplest of the arsinic acids. It is a colorless solid that is soluble in water. Neutralization of cacodylic acid with base gives cacodylate salts, e.g. sodium cacodylate. They are potent herbicides. Cacodylic acid/sodium cacodylate is a buffering agent in the preparation and fixation of biological samples for electron microscopy and in protein crystallography.