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{{chembox
{{Chembox
| ImageFile = Clark 2.svg
| ImageFile = Clark 2.svg
| ImageSize = 150
| ImageSize = 180
| ImageAlt = Structural formula of diphenylcyanoarsine
⚫
| IUPACName = di(phenyl)arsanylformonitrile
| ImageFile1 = Diphenylcyanoarsine-3D-spacefill.png
| OtherNames = Diphenylcyanoarsine<br/> Clark 2<br/> Diphenylarsine cyanide<br/> Diphenylarsinous cyanide<br/> Diphenylarsinecarbonitrile<br/> Arsinous cyanide, diphenyl-<br/> Arsinecarbonitrile, diphenyl-<br/> EINECS 245-716-6<br/> LS-193021
| ImageSize1 = 180
⚫
| Section1 = {{Chembox Identifiers
| ImageAlt1 = Space-filling model of diphenylcyanoarsine
⚫
| CASNo = 23525-22-6
| PIN = Diphenylarsinous cyanide
⚫
| PubChem =
| SystematicName = Diphenylarsanecarbonitrile
⚫
| SMILES = C1=CC=C(C=C1)[As](C#N)C2=CC=CC=C2
| OtherNames = Clark 2<br />
⚫
| InChI = 1/C13H10AsN/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10H
Diphenylarsinecarbonitrile<br />
}}
Diphenylarsine cyanide<br />
⚫
| Section2 = {{Chembox Properties
⚫
Di(phenyl)arsanylformonitrile<br />
| Formula = C<sub>13</sub>H<sub>10</sub>AsN
Diphenylcyanoarsine
⚫
| MolarMass = 255.15 g mol<sup>−1</sup>
⚫
|Section1={{Chembox Identifiers
}}
⚫
| CASNo = 23525-22-6
| CASNo_Ref = {{cascite|correct|??}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = SF5K94TPOF
⚫
| PubChem = 64506
| ChemSpiderID = 58070
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 245-716-6
| MeSHName = Clark+2
⚫
| SMILES = C1=CC=C(C=C1)[As](C#N)C2=CC=CC=C2
| SMILES1 = N#C[As](C1=CC=CC=C1)C1=CC=CC=C1
| StdInChI = 1S/C13H10AsN/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10H
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫
| InChI = 1/C13H10AsN/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10H
| StdInChIKey = BDHNJKLLVSRGDK-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}}}
⚫
|Section2={{Chembox Properties
| C=13 | H=10 | As=1 | N=1
⚫
| MolarMass = 255.002920742 g mol<sup>−1</sup>}}
}}
}}

'''Diphenylcyanoarsine''', also called CLARK 2 ([[Cyanide]]-[[Arsenic]] Kampfstoff) by the Germans, was discovered in 1918 by Sturniolo and Bellinzoni<ref>Sturniolo, G. und Bellinzoni , G. (1919); ''Boll. chim. pharm.'', 58, 409–410</ref> and shortly thereafter used like the related [[Diphenylchlorarsine|Clark 1]] gas by the Germans for chemical warfare in the [[First World War]]. The substance forms colourless, garlic-smelling crystals and causes nausea, vomiting and headaches. It can subsequently lead to e.g. [[pulmonary oedema]] (fluid on the lungs).
'''Diphenylcyanoarsine''', also called Clark 2 (Chlor-Arsen-Kampfstoff 2, being the successor of Clark 1) by the Germans, was discovered in 1918 by Sturniolo and Bellinzoni<ref>Sturniolo, G. und Bellinzoni, G. (1919); ''Boll. chim. pharm.'', 58, 409–410</ref> and shortly thereafter used like the related [[Diphenylchlorarsine|Clark 1]] gas by the Germans for chemical warfare in the [[First World War]]. The substance causes nausea, vomiting, and headaches. It can subsequently lead to e.g. [[pulmonary edema]] (fluid in the lungs).


== See also ==
== See also ==
*[[Cacodyl cyanide]]
*[[Diphenylchlorarsine|Clark 1]]
*[[Diphenylchlorarsine|Clark 1]]
*[[Diphenylaminarsincyanid|Clark 3]]
*[[Chemical weapons]]
*[[Chemical weapons]]


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<references/>
<references/>


[[Category:Chemical weapons]]
{{Chemical agents}}


[[Category:Chemical weapons]]
[[Category:Vomiting agents]]
[[Category:Vomiting agents]]
[[Category:Organoarsenic compounds]]
[[Category:Organoarsenic compounds]]
[[Category:Pulmonary agents]]

[[Category:Phenyl compounds]]
[[de:Diphenylarsincyanid]]
[[Category:Nitriles]]
[[ja:ジフェニルシアノアルシン]]
[[Category:Arsenic(III) compounds]]
[[pl:Difenylocyjanoarsyna]]
[[Category:Substances discovered in the 1910s]]
[[ru:Дифенилцианарсин]]

Latest revision as of 15:34, 18 December 2022

Diphenylcyanoarsine
Structural formula of diphenylcyanoarsine
Space-filling model of diphenylcyanoarsine
Names
Preferred IUPAC name
Diphenylarsinous cyanide
Systematic IUPAC name
Diphenylarsanecarbonitrile
Other names
Clark 2

Diphenylarsinecarbonitrile
Diphenylarsine cyanide
Di(phenyl)arsanylformonitrile

Diphenylcyanoarsine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.041.545 Edit this at Wikidata
EC Number
  • 245-716-6
MeSH Clark+2
UNII
  • InChI=1S/C13H10AsN/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10H checkY
    Key: BDHNJKLLVSRGDK-UHFFFAOYSA-N checkY
  • InChI=1/C13H10AsN/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10H
  • C1=CC=C(C=C1)[As](C#N)C2=CC=CC=C2
  • N#C[As](C1=CC=CC=C1)C1=CC=CC=C1
Properties
C13H10AsN
Molar mass 255.002920742 g mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diphenylcyanoarsine, also called Clark 2 (Chlor-Arsen-Kampfstoff 2, being the successor of Clark 1) by the Germans, was discovered in 1918 by Sturniolo and Bellinzoni[1] and shortly thereafter used like the related Clark 1 gas by the Germans for chemical warfare in the First World War. The substance causes nausea, vomiting, and headaches. It can subsequently lead to e.g. pulmonary edema (fluid in the lungs).

See also[edit]

References[edit]

  1. ^ Sturniolo, G. und Bellinzoni, G. (1919); Boll. chim. pharm., 58, 409–410
source: https://en.wikipedia.org/w/index.php?title=Diphenylcyanoarsine&diff=1128134249&oldid=357629013

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