Cacodyl
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Cacodyl
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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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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Cacodyl Compounds
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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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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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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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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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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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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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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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. This liquid develops white fumes when exposed to air, resulting in a pale flame producing carbon dioxide, water, and arsenic trioxide. It has a nauseating and very disagreeable garlic-like odor. Around 1840, Robert Bunsen did much work on characterizing the compounds in the liquid and its derivatives. His research was important in the development of radical theory Radical theory is an obsolete scientific theory in chemistry describing the structure of organic compounds. The theory wa ...
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Louis Claude Cadet De Gassicourt
Louis Claude Cadet de Gassicourt (24 July 1731 – 17 October 1799) was a French chemist who synthesised the first organometalic compound. He obtained a red liquid by the reaction of potassium acetate with arsenic trioxide. This liquid is known as Cadet's fuming liquid and contains the two compounds cacodyl and cacodyl oxide. Cadet studied at the Collège des Quatre-Nations and became a pharmacist at the Hotel Royal des Invalides in Paris. He was the brother of the pharmacist Antoine-Alexis Cadet de Vaux. Marie Thérèse Françoise Boisselet became his wife in 1771, at that time her son, fathered by Louis XV, was two years old. The boy was adopted by Cadet as Charles-Louis Cadet. Cadet was elected to the American Philosophical Society in 1787. In 1825, botanist Antoine Laurent Apollinaire Fée circumscribed ''Gassicurtia'' which is a genus of lichenized fungi in the family Caliciaceae The Caliciaceae are a family of mostly lichen-forming fungi belonging to the class ...
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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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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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