Cacodyl Chloride
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Cacodyl Chloride
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. Preparation 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: : History Robert Wilhelm Bunsen coined the name kakodyl (later modified to cacodyl ...
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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. History 140px, Cacodyl (tetramethyldiarsine) was one of the first organoarsenic compounds. Surprising for an area now considered of minor importance, organoarsenic chemistry played a prominent role in the history of the field of chemistry. The oldest known organoarsenic compound, the foul smelling cacodyl was reported in "cacodyl" (1760) and is sometimes classified as the first synthetic organometallic compound. The compound Salvarsan was one of the first pharmaceuticals, earning a Nobel ...
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Radical Theory
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. Preamble The term radical was already in use when radical theory was developed. Louis-Bernard Guyton de Morveau introduced the phrase "radical" in 1785 and the phrase was employed by Antoine Lavoisier in 1789 in his Traité Élémentaire de Chimie. A radical was identified as the root base of certain acids (The Latin word "radix" meaning "root"). The combination of a radical with oxygen would result in an acid. For example the radical of acetic acid was called "acetic" and that of muriatic acid (hydrochloric acid) was c ...
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Cacodyl Oxide
Cacodyl oxide is a chemical compound of the formula CH3)2Assub>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. "Cadet's fuming liquid", which is composed of cacodyl and cacodyl oxide, was originally synthesized by heating potassium acetate with arsenic trioxide. It has a disagreeable odor and is toxic. The molecular structure of h2Assub>2O (Ph = phenyl), the tetraphenyl analogue of cacodyl oxide, has been established by X-ray crystallography. See also * Arsenic * Arsine * Cacodylic acid * Lewisite * Cacodyl cyanide Cacodyl cyanide is a highly poisonous organoarsenic compound discovered by Robert Bunsen in the 1840s. It is very volatile and flammable, as it shares the chemical properties of both arsenic and cyanide. Synthesis Cacodyl cyanide can be prepared ... References Cacodyl compounds Foul-smelling chemicals {{organic-compo ...
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Cacodyl Cyanide
Cacodyl cyanide is a highly poisonous organoarsenic compound discovered by Robert Bunsen in the 1840s. It is very volatile and flammable, as it shares the chemical properties of both arsenic and cyanide. Synthesis Cacodyl cyanide can be prepared by reaction of cacodyl oxide with hydrogen cyanide or mercuric cyanide. Properties Cacodyl cyanide is a white solid that is only slightly soluble in water, but very soluble in alcohol and ether. Cacodyl cyanide is highly toxic, producing symptoms of both cyanide and arsenic poisoning. Bunsen described it in the following terms; 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.https://www.supotnitskiy.ru/stat/stat72.htm ...
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Trimethylarsine
Trimethylarsine (abbreviated TMA or TMAs) is the chemical compound with the formula (CH3)3As, commonly abbreviated As Me3 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. Structure and preparation AsMe3 is a pyramidal molecule. The As-C distances average 1.519 Å, and the C-As-C angles are 91.83° Trimethylarsine can be prepared by treatment of arsenic oxide with trimethylaluminium: :As2O3 + 1.5 lMe3sub>2 → 2 AsMe3 + 3/n (MeAl-O)n Occurrence and reactions Trimethylarsine is the volatile byproduct of microbial action on inorganic forms of arsenic which are naturally occurring in rocks and soils at the parts-per-million level. Trimethylarsine has been reported only at trace levels (parts per billion) in landfill gas from Germany, C ...
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Lewisite
Lewisite (L) (A-243) is an organoarsenic compound. It was once manufactured in the U.S., Japan, Germany and the Soviet Union for use as a Chemical warfare, chemical weapon, acting as a vesicant (blister agent) and lung irritant. Although the substance is colorless and odorless in its pure form, impure samples of lewisite are a yellow, brown, violet-black, green, or amber oily liquid with a distinctive odor that has been described as similar to Pelargonium, geraniums. Chemical reactions The compound is prepared by the addition of arsenic trichloride to acetylene in the presence of a suitable catalyst: :AsCl3 + C2H2 → ClCHCHAsCl2 (Lewisite) Lewisite, like other arsenous chlorides, hydrolysis, hydrolyses in water to form hydrochloric acid and chlorovinylarsenous oxide (a less-powerful blister agent): :ClCHCHAsCl2 + 2 H2O → ClCHCHAs(OH)2 + 2 HCl This reaction is accelerated in alkaline solutions, and forms acetylene and trisodium arsenate. Lewisite reacts with metals to form hydrog ...
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Dimethyl(trifluoromethylthio)arsine
Dimethyl(trifluoromethylthio)arsine is an arsenical compound developed by the United States military chemical weapon research program, which is described as "one of the most potent lung irritants known." See also * Cacodyl * Cacodyl cyanide * Diphenylchlorarsine * Lewisite * Methyldichloroarsine * Tetrachlorodinitroethane * Bis(trifluoromethyl) disulfide Bis(trifluoromethyl) disulfide (TFD) is a fluorinated organosulfur compound that was used as a fumigant. It is also an intermediate in the synthesis of triflic acid. It is a volatile liquid that is extremely toxic by inhalation. Synthesis TFD can ... References Arsenical vesicants Arsenic(III) compounds Vomiting agents Trifluoromethylthio compounds Cacodyl compounds {{Organic-compound-stub ...
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Cacodylic Acid
Cacodylic acid is an organoarsenic compound with the formula (CH3)2 AsO2H. 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. History In the 18th century it was found that combining and four equivalents of potassium acetate () gives a product called "Cadet's fuming liquid" which contains cacodyl oxide, and cacodyl, . Early research into "cacodyls" was reported 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 wit ...
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Ligand
In coordination chemistry, a ligand is an ion or molecule (functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's electron pairs, often through Lewis bases. The nature of metal–ligand bonding can range from covalent to ionic. Furthermore, the metal–ligand bond order can range from one to three. Ligands are viewed as Lewis bases, although rare cases are known to involve Lewis acidic "ligands". Metals and metalloids are bound to ligands in almost all circumstances, although gaseous "naked" metal ions can be generated in a high vacuum. Ligands in a complex dictate the reactivity of the central atom, including ligand substitution rates, the reactivity of the ligands themselves, and redox. Ligand selection requires critical consideration in many practical areas, including bioinorganic and medicinal chemistry, homogeneous catalysis, and environmental chemi ...
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Chemical Weapon
A chemical weapon (CW) is a specialized munition that uses chemicals formulated to inflict death or harm on humans. According to the Organisation for the Prohibition of Chemical Weapons (OPCW), this can be any chemical compound intended as a weapon "or its precursor that can cause death, injury, temporary incapacitation or sensory irritation through its chemical action. Munitions or other delivery devices designed to deliver chemical weapons, whether filled or unfilled, are also considered weapons themselves." Chemical weapons are classified as weapons of mass destruction (WMD), though they are distinct from nuclear weapons, biological weapons, and radiological weapons. All may be used in warfare and are known by the military acronym NBC (for nuclear, biological, and chemical warfare). Weapons of mass destruction are distinct from conventional weapons, which are primarily effective due to their explosive, kinetic, or incendiary potential. Chemical weapons can be widely dispe ...
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World War I
World War I (28 July 1914 11 November 1918), often abbreviated as WWI, was one of the deadliest global conflicts in history. Belligerents included much of Europe, the Russian Empire, the United States, and the Ottoman Empire, with fighting occurring throughout Europe, the Middle East, Africa, the Pacific, and parts of Asia. An estimated 9 million soldiers were killed in combat, plus another 23 million wounded, while 5 million civilians died as a result of military action, hunger, and disease. Millions more died in genocides within the Ottoman Empire and in the 1918 influenza pandemic, which was exacerbated by the movement of combatants during the war. Prior to 1914, the European great powers were divided between the Triple Entente (comprising France, Russia, and Britain) and the Triple Alliance (containing Germany, Austria-Hungary, and Italy). Tensions in the Balkans came to a head on 28 June 1914, following the assassination of Archduke Franz Ferdin ...
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