Cacodyl cyanide

Cacodyl cyanide
Names
Skeletal formula
Ball-and-stick model based on crystallography^[1]^[2]
Preferred IUPAC name Dimethylarsinous cyanide
Other names Cyanodimethylarsine Dimethylcyanoarsine Cyanide of cacodyl
Identifiers
CAS Number	683-45-4
3D model (JSmol)	Interactive image
ChemSpider	12169
PubChem CID	12690
RTECS number	CH2100000
CompTox Dashboard (EPA)	DTXSID50218451
InChI InChI=1S/C3H6AsN/c1-4(2)3-5/h1-2H3 Key: BXASHBJZPLFFPH-UHFFFAOYSA-N
SMILES C[As](C)C#N
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

Chemical compound

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.

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".

Blood agents

Blister agents

Arsenicals	Ethyldichloroarsine (ED) Methyldichloroarsine (MD) Phenyldichloroarsine (PD) Lewisite (L) Lewisite 2 (L2) Lewisite 3 (L3)
Sulfur mustards	Levinstein mustard (EA-229) T Q CEES
Nitrogen mustards	HN1 HN2 HN3 TL-301
Nettle agents	Phosgene oxime (CX)
Other	KB-16 Dibutylchloromethyltin chloride Selenium oxychloride

Nerve agents

G-agents	Tabun (GA) Sarin (GB) Chlorosarin (ClGB) Thiosarin (SGB) Soman (GD) Chlorosoman (ClGD) Ethylsarin (GE) GH Cyclosarin (GF) GP Fluorotabun EA-1356 EA-4352 Crotylsarin
V-agents	EA-2192 EA-3148 VE VG VM VP VR VS VX EA-1763 Chinese VX V-sub x (GD-7)
GV agents	GV (EA-5365)
Novichok agents	A-208 A-232 A-234 A-242 A-262 C01-A035 C01-A039 C01-A042
Carbamates	Dimethylcarbamoyl fluoride EA-3887 EA-3887A EA-3966 EA-3990 EA-4056 T-1123 T-1152 T-1194 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) TL-599 TL-1238 TL-1299 TL-1317 Miotine (AR-28/T-1843) 3152 CT 4-686-293-01 (Agent 1-10)
Other	Diisopropyl fluorophosphate Dicyclohexyl phosphorofluoridate EA-2012 EA-2054 EA-2098 EA-2613 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Neopentylene fluorophosphate Selenophos Phospholine R-16661 Ro 3-0422 Methanesulfonyl fluoride Dimefox (TL-792) MSPI
Precursors	Acetonitrile AT ATO AlP A.P.C. complex Chlorosarin Chlorosoman Cyclohexanol 1,8-Dibromooctane N,N-Diisopropylaminoethanol (KB) EA-1250 DIHP ZS DEHP EA-1224 Dimethylamidophosphoric dichloride Dimethylamidophosphoric dicyanide DMHP Ethylphosphonoselenoic dichloride Formaldoxime Nital 4-Hydroxycoumarin Isopropyl alcohol (TB) Methyldichlorophosphine (SW) Methylphosphonyl difluoride (difluoro) (DF) Methylphosphonyl dichloride (dichloro) Nitromethane OPA mixture Phosphoryl chloride Phosphorus pentachloride Phosphorus trichloride (TH) Pinacolone Pinacolyl alcohol Phenacyl chloride QL 2,4,5-Trichlorophenol 3,3,5-Trimethylcyclohexanol Triethyl phosphite Trimethyl phosphite TC TG