Cacodyl cyanide

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Cacodyl cyanide
Cacodyl cyanide.svg
Cacodyl-cyanide-from-xtal-3D-bs-17.png
Names
Preferred IUPAC name
Dimethylarsinous cyanide
Other names
Cyanodimethylarsine
Dimethylcyanoarsine
Cyanide of cacodyl
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
RTECS number
  • CH2100000
  • InChI=1S/C3H6AsN/c1-4(2)3-5/h1-2H3
    Key: BXASHBJZPLFFPH-UHFFFAOYSA-N
  • C[As](C)C#N
Properties
C3H6AsN
Molar mass 131.010 g·mol−1
AppearanceWhite solid
Melting point 33 °C (91 °F; 306 K)
Boiling point 140 °C (284 °F; 413 K)
Slightly soluble
Solubility Very soluble in alcohol and ether
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Extremely toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cacodyl cyanide is a highly toxic organoarsenic compound discovered by Robert Bunsen in the 1840s. [3] [4] [5] It is very volatile and flammable, as it shares the chemical properties of both arsenic and cyanide.

Contents

Synthesis

Cacodyl cyanide can be prepared by reaction of cacodyl oxide with hydrogen cyanide or mercuric cyanide. [6]

Properties

Cacodyl cyanide is a white solid that is only slightly soluble in water, but very soluble in alcohol and ether. [6]

Cacodyl cyanide is highly toxic, producing symptoms of both cyanide and arsenic poisoning. Bunsen described it [7] in the following terms;

This substance is extraordinarily poisonous, and for this reason its preparation and purification can only be carried on in the open air; indeed, under these circumstances, it is necessary for the operator to breathe through a long open tube so as to insure the inspiration of air free from impregnation with any trace of the vapor of this very volatile compound. If only a few grains of this substance be allowed to evaporate in a room at the ordinary temperature, the effect upon any one inspiring the air is that of sudden giddiness and insensibility, amounting to complete unconsciousness.

It is also explosive, and Bunsen himself was severely injured in the course of his experiments with cacodyl cyanide. The Russian military tested cacodyl cyanide on cats as a potential chemical weapon for filling shells in late 1850s, but while it was found to be a potent lachrymatory agent, all cats survived and it was ultimately considered unsuitable for military use. [8] [9] [10] Any experiment or contact with cacodyl cyanide requires extreme care and caution as it is highly dangerous.

See also

Related Research Articles

<span class="mw-page-title-main">Arsenic</span> Chemical element, symbol As and atomic number 33

Arsenic is a chemical element; it has symbol As and atomic number 33. Arsenic occurs in many minerals, usually in combination with sulfur and metals, but also as a pure elemental crystal. Arsenic is a metalloid. It has various allotropes, but only the grey form, which has a metallic appearance, is important to industry.

<span class="mw-page-title-main">Cyanide</span> Any molecule with a cyano group (–C≡N)

In chemistry, a cyanide is a chemical compound that contains a C≡N functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom.

<span class="mw-page-title-main">Organometallic chemistry</span> Study of organic compounds containing metal(s)

Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide, cyanide, or carbide, are generally considered to be organometallic as well. Some related compounds such as transition metal hydrides and metal phosphine complexes are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term "metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, alkoxides, dialkylamides, and metal phosphine complexes are representative members of this class. The field of organometallic chemistry combines aspects of traditional inorganic and organic chemistry.

<span class="mw-page-title-main">Thallium</span> Chemical element, symbol Tl and atomic number 81

Thallium is a chemical element; it has symbol Tl and atomic number 81. It is a gray post-transition metal that is not found free in nature. When isolated, thallium resembles tin, but discolors when exposed to air. Chemists William Crookes and Claude-Auguste Lamy discovered thallium independently in 1861, in residues of sulfuric acid production. Both used the newly developed method of flame spectroscopy, in which thallium produces a notable green spectral line. Thallium, from Greek θαλλός, thallós, meaning "green shoot" or "twig", was named by Crookes. It was isolated by both Lamy and Crookes in 1862; Lamy by electrolysis, and Crookes by precipitation and melting of the resultant powder. Crookes exhibited it as a powder precipitated by zinc at the international exhibition, which opened on 1 May that year.

<span class="mw-page-title-main">Poison</span> Substance that causes death, injury or harm to organs

A poison is any chemical substance that is harmful or lethal to living organisms. The term is used in a wide range of scientific fields and industries, where it is often specifically defined. It may also be applied colloquially or figuratively, with a broad sense.

Bioaccumulation is the gradual accumulation of substances, such as pesticides or other chemicals, in an organism. Bioaccumulation occurs when an organism absorbs a substance faster than it can be lost or eliminated by catabolism and excretion. Thus, the longer the biological half-life of a toxic substance, the greater the risk of chronic poisoning, even if environmental levels of the toxin are not very high. Bioaccumulation, for example in fish, can be predicted by models. Hypothesis for molecular size cutoff criteria for use as bioaccumulation potential indicators are not supported by data. Biotransformation can strongly modify bioaccumulation of chemicals in an organism.

<span class="mw-page-title-main">Arsine</span> Chemical compound

Arsine (IUPAC name: arsane) is an inorganic compound with the formula AsH3. This flammable, pyrophoric, and highly toxic pnictogen hydride gas is one of the simplest compounds of arsenic. Despite its lethality, it finds some applications in the semiconductor industry and for the synthesis of organoarsenic compounds. The term arsine is commonly used to describe a class of organoarsenic compounds of the formula AsH3−xRx, where R = aryl or alkyl. For example, As(C6H5)3, called triphenylarsine, is referred to as "an arsine".

Cyanogen is the chemical compound with the formula (CN)2. The simplest stable carbon nitride, it is a colorless and highly toxic gas with a pungent odor. The molecule is a pseudohalogen. Cyanogen molecules consist of two CN groups – analogous to diatomic halogen molecules, such as Cl2, but far less oxidizing. The two cyano groups are bonded together at their carbon atoms: N≡C‒C≡N, although other isomers have been detected. The name is also used for the CN radical, and hence is used for compounds such as cyanogen bromide (NCBr) (but see also Cyano radical.)

A blood agent is a toxic chemical agent that affects the body by being absorbed into the blood. Blood agents are fast-acting, potentially lethal poisons that typically manifest at room temperature as volatile colorless gases with a faint odor. They are either cyanide- or arsenic-based.

<span class="mw-page-title-main">Cacodyl</span> Chemical compound

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.

<span class="mw-page-title-main">Cacodylic acid</span> Chemical compound

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.

<span class="mw-page-title-main">Cacodyl oxide</span> Chemical compound

Cacodyl oxide is a chemical compound of the formula [(CH3)2As]2O. This organoarsenic compound is primarily of historical significance since it is sometimes considered to be the first organometallic compound synthesized in relatively pure form.

<span class="mw-page-title-main">Arsenic trichloride</span> Chemical compound

Arsenic trichloride is an inorganic compound with the formula AsCl3, also known as arsenous chloride or butter of arsenic. This poisonous oil is colourless, although impure samples may appear yellow. It is an intermediate in the manufacture of organoarsenic compounds.

Trimethylarsine (abbreviated TMA or TMAs) is the chemical compound with the formula (CH3)3As, commonly abbreviated AsMe3 or TMAs. This organic derivative of arsine has been used as a source of arsenic in microelectronics industry, a building block to other organoarsenic compounds, and serves as a ligand in coordination chemistry. It has distinct "garlic"-like smell. Trimethylarsine had been discovered as early as 1854.

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.

<span class="mw-page-title-main">Cadet's fuming liquid</span> Mixture of organoarsenic compounds

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).

<span class="mw-page-title-main">Robert Bunsen</span> German chemist (1811–1899)

Robert Wilhelm Eberhard Bunsen was a German chemist. He investigated emission spectra of heated elements, and discovered caesium and rubidium with the physicist Gustav Kirchhoff. The Bunsen–Kirchhoff Award for spectroscopy is named after Bunsen and Kirchhoff.

<span class="mw-page-title-main">Dimethyl trisulfide</span> Chemical compound

Dimethyl trisulfide (DMTS) is an organic chemical compound and the simplest organic trisulfide, with the chemical formula CH3SSSCH3. It is a flammable liquid with a foul odor, which is detectable at levels as low as 1 part per trillion.

Radical theory is an obsolete scientific theory in chemistry describing the structure of organic compounds. The theory was pioneered by Justus von Liebig, Friedrich Wöhler and Auguste Laurent around 1830 and is not related to the modern understanding of free radicals. In this theory, organic compounds were thought to exist as combinations of radicals that could be exchanged in chemical reactions just as chemical elements could be interchanged in inorganic compounds.

<span class="mw-page-title-main">Mercury oxycyanide</span> Chemical compound

Mercury oxycyanide is a chemical compound, an organomercury derivative. It is both explosive and highly toxic, producing symptoms of both mercury and cyanide poisoning following exposure.

References

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  2. Britton, D.; Young, V. G.; Schlemper, E. O. (2002). "Intermolecular interactions in cyanodimethylarsine and cyanodimethylstibine". Acta Crystallogr. C . 58 (5): m307–m309. Bibcode:2002AcCrC..58M.307B. doi: 10.1107/S0108270102006030 . PMID   11983976.
  3. Lee FA, Thing C, Dehn WM (1923). "Some cacodyl derivatives". J. Am. Chem. Soc. 45 (12): 2996–2998. doi:10.1021/ja01665a027.
  4. Morgan GT, Yarsley VE (1926). "Dimethylstibine cyanide, an analogue of cacodyl cyanide". Proc. R. Soc. Lond. A. 110 (755): 534–537. Bibcode:1926RSPSA.110..534M. doi: 10.1098/rspa.1926.0031 .
  5. Seyferth D (2001). "Cadet's Fuming Arsenical Liquid and the Cacodyl Compounds of Bunsen". Organometallics. 20 (8): 1488–1498. doi: 10.1021/om0101947 .
  6. 1 2 Organic Arsenical Compounds. 1923.
  7. Roscoe, H. E. (28 April 1881). "Scientific Worthies" (PDF). Nature. 23 (600): 597–600. Bibcode:1881Natur..23..597R. doi:10.1038/023597a0. Archived (PDF) from the original on 2021-12-12.
  8. Curry R (11 May 2015). "Cacodyl Cyanide Chemistry Catastrophe - Professor Bunsen's Aphasia, Black Tongue, Blind Eye & Nearly Fatal Poisoning". Lateral Science.
  9. Freemantle M (26 January 2019). "Cacodyl". chemistryworld.com.
  10. "ЗАБЫТАЯ ХИМИЧЕСКАЯ ВОЙНА 1915-1918 гг. I. Отравляющие вещества и химическое оружие Первой мировой войны".