Cacodyl cyanide
Skeletal formula | |
Ball-and-stick model based on crystallography[1][2] | |
Names | |
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Preferred IUPAC name Dimethylarsinous cyanide | |
Other names Cyanodimethylarsine Dimethylcyanoarsine Cyanide of cacodyl | |
Identifiers | |
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Properties | |
Chemical formula | C3H6AsN |
Molar mass | 131.010 g·mol−1 |
Appearance | White solid |
Melting point | 33 °C (91 °F; 306 K) |
Boiling point | 140 °C (284 °F; 413 K) |
Solubility in water | 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). Infobox references |
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.
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
- Cacodyl
- Cyanogen bromide
- Dimethyl(trifluoromethylthio)arsine
- Diphenylcyanoarsine
- Mercury(II) cyanide
- Mercury oxycyanide
- Methyldichloroarsine
- Trimethylarsine
- Trimethylsilyl cyanide
References
- ^ Britton, D.; Young Junior, V.G.; Schlemper, E.O. (2002). "CSD Entry: CNMARS01". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/cc69jss. Retrieved 2022-08-10.
- ^ 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.
- ^ Lee FA, Thing C, Dehn WM (1923). "Some cacodyl derivatives". J. Am. Chem. Soc. 45 (12): 2996–2998. doi:10.1021/ja01665a027.
- ^ 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.
- ^ Seyferth D (2001). "Cadet's Fuming Arsenical Liquid and the Cacodyl Compounds of Bunsen". Organometallics. 20 (8): 1488–1498. doi:10.1021/om0101947.
- ^ a b Organic Arsenical Compounds. 1923.
- ^ 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.
- ^ Curry R (11 May 2015). "Cacodyl Cyanide Chemistry Catastrophe - Professor Bunsen's Aphasia, Black Tongue, Blind Eye & Nearly Fatal Poisoning". Lateral Science.
- ^ Freemantle M (26 January 2019). "Cacodyl". chemistryworld.com.
- ^ "ЗАБЫТАЯ ХИМИЧЕСКАЯ ВОЙНА 1915-1918 гг. I. Отравляющие вещества и химическое оружие Первой мировой войны".
- v
- t
- e
- Agents used in chemical warfare
- incapacitation
- riot control
- Cyanogen
- Cyanogen bromide
- Cyanogen chloride (CK)
- Hydrogen cyanide (AC)
- Arsine
- Cacodyl cyanide
- Cacodyl oxide
- Hydrogen sulfide
- Phosphine
- Carbon monoxide
- Phosphorus trifluoride
- Methyl cyanoformate
- Iron pentacarbonyl
- Nickel tetracarbonyl
- 2,3,7,8-Tetrachlorodibenzodioxin
- Glycolonitrile
- Lactonitrile
- Acetone cyanohydrin
- Stibine
- Chloral cyanohydrin
Arsenicals | |
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Sulfur mustards |
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Nitrogen mustards | |
Nettle agents |
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Other |
- Anatoxin-a
- Saxitoxin (TZ)
- Bungarotoxin
- Botulinum toxin (BTX)
- Tetanospasmin (TeNT)
- Ryanodine
- Ciguatoxin (CTX)
- Guanitoxin (GTX)
- Chlorophenylsilatrane
- Palytoxin (PTX)
- Maitotoxin (MTX)
- Tetrodotoxin
- Aconitine
- Brevetoxin (PbTX)
- Strychnine
- Antillatoxin (ATX)
- Tetraethyllead
- Dimethylmercury
- HN1 hydrochloride
- HN2 hydrochloride
- HN3 hydrochloride
- A-8564
- Picrotoxin
- Sulfuryl fluoride
- Tremorine
- Oxotremorine
- Batrachotoxin
- Tetramethylenedisulfotetramine (TETS)
- Bicyclic phosphates
- Cloflubicyne
- Trimethylolpropane phosphite
- Domoic acid
choking agents
- Chlorine
- Bromine
- Phosgene (CG)
- Fluorine
- Perfluoroisobutene
- Chloropicrin (PS)
- Dimethyl(trifluoromethylthio)arsine
- Diphosgene (DP)
- Disulfur decafluoride (Z)
- Acrolein
- Ethyl bromoacetate
- Perchloromethyl mercaptan
- Phenylcarbylamine chloride
- Tetranitromethane
- Tetrachlorodinitroethane
- Chlorine trifluoride
- Perchloryl fluoride
- Cadmium oxide
- Cadmium chloride
- Mercuric chloride
- Selenium dioxide
- Selenoyl fluoride
- Trifluoronitrosomethane
- Trichloronitrosomethane
- Nitric oxide
- Nitrogen dioxide
- Dinitrogen tetroxide
- Sulfur dioxide
- Phosphorus trichloride
- Methyl isocyanate
- Ethenone
- Methyl vinyl ketone
- Trifluoroacetyl chloride
- Salcomine
- Fluomine
- Uranium hexafluoride
- Diborane
- Green Cross
- Adamsite (DM)
- Chloropicrin
- Litharge-glycerine
- Diphenylchlorarsine
- Diphenylcyanoarsine
- Cacodyl cyanide
- o-Dianisidine
agents
- BZ (CS-4030)
- Apomorphine
- Butyrophenone
- EA-4941 (CS-4640)
- Etorphine
- EA-2092
- CS-4297
- Etoxadrol
- Dimethylheptylpyran (DMHP)
- EA-2148
- EA-3167
- EA-3443
- Pethidine
- EA-3580
- Ibogaine
- EA-3834
- Kolokol-1
- LSD-25
- PAVA spray
- Psilocybin
- Sleeping gas
- Carfentanil
- JB-318
- JB-336
- CS-27349
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,668
- Benperidol
- Desflurane
- Enflurane
- Bufotenin
- Isoflurane
- Halothane
- Sevoflurane
- Pentazocine
- Procarbazine
- Fluphenazine
- Chlorpromazine
agents
- Xylyl bromide
- Pepper spray (OC)
- Mace (spray)
- CN
- CS
- CR
- CNS
- Benzyl chloride
- Benzyl bromide
- Benzyl iodide
- Bromobenzyl cyanide
- Thiophosgene
- Chloroacetone
- Bromoacetone
- Bromomethyl ethyl ketone
- Acrolein
- Phenacyl bromide
- Chloroacetophenone oxime
- Ethyl bromoacetate
- Ethyl iodoacetate
- Iodoacetone
- Allyl isothiocyanate
- Hexamethylene diisocyanate
- Crotonaldehyde
- Abrin
- Aconitine
- Cyclopiazonic acid
- Histrionicotoxins
- Aflatoxins
- Anatoxin-a
- Batrachotoxin
- Botulinum toxin
- Brevetoxin
- Ciguatoxin
- Domoic acid
- Enterotoxin type B
- Grayanotoxin
- Guanitoxin
- Maitotoxin
- Modeccin
- Palytoxin
- Ricin
- Saxitoxin
- Shiga toxin
- T-2 mycotoxin
- Tetanospasmin
- Tetrodotoxin
- Volkensin
- Veratridine
- Methyl fluoroacetate
- Napalm (variants and mixtures)
- Fluoroethyl fluoroacetate
- Depleted uranium
- post-combustion uranium oxides
- Plutonium and its compounds
- Polonium
- White phosphorus