24:
37:
291:
198:
47:
433:
704:
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 with a black coating, even when no further evil effects are
446:
340:
730:, which resulted in a wide use of cacodyl in research laboratories. Afterward interest in the toxic, malodorous compound decreased. During
36:
756:
23:
305:
906:
501:
148:
248:
269:
610:
A more efficient synthesis was later developed which started from the dimethyl arsine chloride and dimethyl arsine:
901:
453:
155:
46:
205:
738:
was considered, but it was never used in the war. Inorganic chemists discovered the properties of cacodyl as a
497:
829:
727:
493:
410:
193:
505:
653:
562:. A subsequent reduction yields a mixture of several methylated arsenic compounds including dicacodyl.
695:
66:
286:
519:
114:
855:
833:
710:
Work on cacodyl led Bunsen to the postulation of "methyl radicals" as part of the then-current
504:). It is a poisonous oily liquid with an extremely unpleasant garlicky odor. Cacodyl undergoes
555:
878:
870:
809:
680:
559:
515:
368:
257:
175:
771:
766:
735:
699:
565:
The global reaction (mass balance) corresponding to the oxide formation is the following:
124:
290:
197:
751:
723:
711:
688:
424:
895:
776:
684:
186:
237:
731:
396:
166:
660:(later modified to cacodyl in English) for the dimethylarsinyl radical, (CH
761:
874:
224:
206:
883:
814:
797:
798:"Cadet's Fuming Arsenical Liquid and the Cacodyl Compounds of Bunsen"
739:
691:
compound ever discovered (even though arsenic is not a true metal).
423:
Except where otherwise noted, data are given for materials in their
838:
Jahresberichte über die
Fortschritte der Physischen Wissenschaften
154:
147:
137:
694:
From it other compounds were made, such as cacodyl fluoride,
274:
45:
35:
441:
554:) was first prepared by Cadet by the reaction of
236:
123:
702:, was particularly awful. In Bunsen's words "
538:A mixture of dicacodyl and cacodyl oxide ((CH
8:
496:compound that constitutes a major part of "
289:
196:
174:
15:
882:
813:
256:
856:"The Crystal Structure of Arsenomethane"
640:
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628:
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591:
587:
583:
579:
575:
571:
788:
345:
310:
285:
187:
854:John H. Burns and Jürg Waser (1957).
722:Cacodyl was used to try to prove the
317:Key: RSKPLCGMBWEANE-UHFFFAOYSA-N
314:InChI=1S/C4H12As2/c1-5(2)6(3)4/h1-4H3
7:
324:InChI=1/C4H12As2/c1-5(2)6(3)4/h1-4H3
757:Dimethyl(trifluoromethylthio)arsine
327:Key: RSKPLCGMBWEANE-UHFFFAOYAG
227:
500:" (named after the French chemist
14:
502:Louis Claude Cadet de Gassicourt
431:
380:
22:
687:and is considered the earliest
427:(at 25 °C , 100 kPa).
386:
40:Ball and stick model of cacodyl
374:
50:Space-filling model of cacodyl
1:
683:and (for over six years) by
698:, et cetera. One compound,
31:
923:
796:Seyferth, Dietmar (2001).
672:("evil-smelling") and ὕλη
421:
361:
336:
301:
107:
77:
65:
60:
30:
21:
734:the use of cacodyl as a
514:is also the name of the
907:Foul-smelling chemicals
742:for transition metals.
679:It was investigated by
411:Magnetic susceptibility
506:spontaneous combustion
51:
41:
830:Berzelius, Jöns Jacob
654:Robert Wilhelm Bunsen
498:Cadet's fuming liquid
91:Bis(dimethylarsenic)(
80:Tetramethyldiarsenic(
49:
39:
728:Jöns Jacob Berzelius
67:Preferred IUPAC name
875:10.1021/ja01561a020
668:As, from the Greek
474:tetramethyldiarsine
404: g·mol
102:Tetramethyldiarsine
71:Tetramethyldiarsane
18:
454:Infobox references
52:
42:
16:
902:Cacodyl compounds
815:10.1021/om0101947
556:potassium acetate
462:Chemical compound
460:
459:
270:CompTox Dashboard
156:Interactive image
149:Interactive image
56:
55:
914:
888:
886:
863:J. Am. Chem. Soc
860:
846:
845:
826:
820:
819:
817:
808:(8): 1488–1498.
793:
696:cacodyl chloride
681:Edward Frankland
656:coined the name
644:
606:
560:arsenic trioxide
516:functional group
468:, also known as
444:
438:
435:
434:
417:-99.9·10 cm/mol
403:
388:
382:
376:
369:Chemical formula
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858:
853:
850:
849:
828:
827:
823:
802:Organometallics
795:
794:
790:
785:
772:Cacodyl cyanide
767:Trimethylarsine
748:
736:chemical weapon
720:
700:cacodyl cyanide
670:κακώδης kakōdēs
667:
663:
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449: ?)
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5:
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869:(4): 859–864.
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752:Cacodylic acid
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724:radical theory
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712:radical theory
689:organometallic
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425:standard state
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777:Cacodyl oxide
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685:Robert Bunsen
682:
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494:organoarsenic
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188:ECHA InfoCard
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20:
866:
862:
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721:
718:Applications
709:
703:
693:
678:
676:("matter").
673:
669:
657:
652:
609:
564:
537:
511:
510:
508:in dry air.
473:
469:
465:
464:
108:Identifiers
96:
92:
90:
85:
81:
78:Other names
732:World War I
534:Preparation
362:Properties
194:100.006.766
896:Categories
884:1911/18207
844:: 526–539.
783:References
705:noticeable
623:Cl + As(CH
546:As–O–As(CH
397:Molar mass
348:((C)C)(C)C
258:11N299093L
167:ChemSpider
136:3D model (
115:CAS Number
834:"Kakodyl"
574:COOK + As
470:dicacodyl
215:207-440-4
207:EC Number
832:(1841).
762:Lewisite
746:See also
492:, is an
484:As–As(CH
413:(χ)
353:C(C)(C)C
125:471-35-2
17:Cacodyl
658:kakodyl
649:History
594:O + 2 K
520:radical
512:Cacodyl
466:Cacodyl
447:what is
445: (
402:209.983
225:PubChem
740:ligand
631:H → As
602:+ 2 CO
582:→ ((CH
442:verify
439:
341:SMILES
61:Names
859:(PDF)
643:+ HCl
615:As(CH
558:with
476:, (CH
306:InChI
238:79018
176:71351
138:JSmol
707:".
674:hylē
570:4 CH
530:As.
249:UNII
879:hdl
871:doi
810:doi
726:of
635:(CH
590:As)
522:(CH
518:or
472:or
275:EPA
228:CID
898::
877:.
867:79
865:.
861:.
842:20
840:.
836:.
806:20
804:.
800:.
714:.
598:CO
387:As
384:12
97:As
93:As
86:As
82:As
887:.
881::
873::
818:.
812::
666:2
664:)
662:3
641:4
639:)
637:3
633:2
629:2
627:)
625:3
621:2
619:)
617:3
604:2
600:3
596:2
592:2
588:2
586:)
584:3
580:3
578:O
576:2
572:3
552:2
550:)
548:3
544:2
542:)
540:3
528:2
526:)
524:3
490:2
488:)
486:3
482:2
480:)
478:3
437:Y
390:2
381:H
378:4
375:C
277:)
273:(
140:)
99:)
95:—
88:)
84:—
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