| Revision as of 11:11, 4 August 2014 editKintetsubuffalo (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers203,496 editsNo edit summary← Previous edit | Revision as of 21:49, 23 June 2015 edit undoDePiep (talk | contribs)Extended confirmed users294,285 editsm Replace/remove deprecated parameters. Simplify ws. rm using Template:Pubchemcite. (via AWB script)Next edit → | ||
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| | verifiedrevid = 433275081 | | verifiedrevid = 433275081 | ||
| | ImageFileR1 = Cacodyl-from-xtal-1988-3D-balls.png | | ImageFileR1 = Cacodyl-from-xtal-1988-3D-balls.png | ||
| | |
| ImageNameR1 = Ball and stick model of cacodyl | ||
| | ImageFileL1 = Struktur Kakodyl.png | | ImageFileL1 = Struktur Kakodyl.png | ||
| | |
| ImageNameL1 = Structural formula of cacodyl | ||
| | IUPACName = Tetramethyldiarsane | | IUPACName = Tetramethyldiarsane | ||
| | OtherNames = Tetramethyldiarsenic(''As''—''As'')<br /> | | OtherNames = Tetramethyldiarsenic(''As''—''As'')<br /> | ||
| Tetramethyldiarsine | Tetramethyldiarsine | ||
| | |
|Section1={{Chembox Identifiers | ||
| | |
| CASNo = 471-35-2 | ||
| | |
| CASNo_Ref = {{cascite|correct|??}} | ||
| | |
| PubChem = 79018 | ||
| ⚫ | | ChemSpiderID = 71351 | ||
| | PubChem_Ref = {{Pubchemcite|correct|PubChem}} | |||
| ⚫ | | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ||
| ⚫ | | |
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| ⚫ | | EINECS = 207-440-4 | ||
| ⚫ | | |
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| ⚫ | | SMILES = ((C)C)(C)C | ||
| ⚫ | | |
||
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| SMILES1 = C(C)(C)C | ||
| ⚫ | | StdInChI = 1S/C4H12As2/c1-5(2)6(3)4/h1-4H3 | ||
| ⚫ | | |
||
| ⚫ | | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | ||
| ⚫ | | |
||
| ⚫ | | InChI = 1/C4H12As2/c1-5(2)6(3)4/h1-4H3 | ||
| ⚫ | | |
||
| ⚫ | | StdInChIKey = RSKPLCGMBWEANE-UHFFFAOYSA-N | ||
| ⚫ | | |
||
| ⚫ | | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | ||
| ⚫ | | |
||
| ⚫ | | InChIKey = RSKPLCGMBWEANE-UHFFFAOYAG}} | ||
| ⚫ | | |
||
| ⚫ | |Section2={{Chembox Properties | ||
| ⚫ | | |
||
| | C=4 | H=12 | As=2 | |||
| ⚫ | | |
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| ⚫ | |Section3={{Chembox Hazards | ||
| | C = 4 | |||
| | H = 12 | |||
| | As = 2 | |||
| | ExactMass = 209.937093218 g mol<sup>−1</sup>}} | |||
| ⚫ | | |
||
| | MainHazards = | | MainHazards = | ||
| | FlashPt = | | FlashPt = | ||
| | |
| AutoignitionPt = }} | ||
| }} | }} | ||
| '''Cacodyl''', '''dicacodyl''', '''tetramethyldiarsine''', '''alkarsine''' or minor part of the "]" (after the French chemist ]) (CH<sub>3</sub>)<sub>2</sub>As—As(CH<sub>3</sub>)<sub>2</sub> is a poisonous oily liquid with a garlicky odor. Cacodyl undergoes ] in dry air. | '''Cacodyl''', '''dicacodyl''', '''tetramethyldiarsine''', '''alkarsine''' or minor part of the "]" (after the French chemist ]) (CH<sub>3</sub>)<sub>2</sub>As—As(CH<sub>3</sub>)<sub>2</sub> is a poisonous oily liquid with a garlicky odor. Cacodyl undergoes ] in dry air. | ||
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| }} | }} | ||
| *{{cite journal | *{{cite journal | ||
| | title = Cadet's Fuming Arsenical Liquid and the Cacodyl Compounds of Bunsen | |||
| | first = Dietmar | |||
| | last = Seyferth | |||
| | journal = Organometallics | |||
| | year = 2001 | |||
| | volume = 20 | |||
| | issue =8 | |||
| | pages = 1488–1498 | |||
| | doi = 10.1021/om0101947 | |||
| | url = http://pubs.acs.org/cgi-bin/abstract.cgi/orgnd7/2001/20/i08/abs/om0101947.html}} | |||
| ] | ] | ||
Revision as of 21:49, 23 June 2015
{{Chembox
| verifiedrevid = 433275081
| ImageFileR1 = Cacodyl-from-xtal-1988-3D-balls.png
| ImageNameR1 = Ball and stick model of cacodyl
| ImageFileL1 = Struktur Kakodyl.png
| ImageNameL1 = Structural formula of cacodyl
| IUPACName = Tetramethyldiarsane
| OtherNames = Tetramethyldiarsenic(As—As)
Tetramethyldiarsine
|Section1=! colspan=2 style="background: #f8eaba; text-align: center;" |Identifiers
|-
|
CAS Number|
|-
|
3D model (JSmol)|
|-
|
|-
| ECHA InfoCard
| 100.006.766 
|-
| EC Number
|
- 207-440-4
|-
|
PubChem CID|
|-
|
CompTox Dashboard (EPA)|
|-
| colspan="2" |
InChI- InChI=1S/C4H12As2/c1-5(2)6(3)4/h1-4H3Key: RSKPLCGMBWEANE-UHFFFAOYSA-N
- InChI=1/C4H12As2/c1-5(2)6(3)4/h1-4H3Key: RSKPLCGMBWEANE-UHFFFAOYAG
|-
| colspan="2" |
SMILES- ((C)C)(C)C
- C(C)(C)C
|- |Section2=! colspan=2 style="background: #f8eaba; text-align: center;" |Properties
|-
|
Chemical formula| C4H12As2
|- | Molar mass
| 209.983 g·mol
|- Cacodyl, dicacodyl, tetramethyldiarsine, alkarsine or minor part of the "Cadet's fuming liquid" (after the French chemist Louis Claude Cadet de Gassicourt) (CH3)2As—As(CH3)2 is a poisonous oily liquid with a garlicky odor. Cacodyl undergoes spontaneous combustion in dry air.
Preparation
Cacodyl oxide is prepared by the reaction of potassium acetate with arsenic trioxide.
- 4 CH3CO2K + As2O3 → As2(CH3)4 + 2 K2CO3 + 2 CO2
A subsequent reduction or disproportionation of the substance under the reaction conditions yields a mixture of several methylated arsenic compounds.
A far better synthesis was developed which started from the dimethyl arsine chloride and dimethyl arsine.
- As(CH3)2Cl + As(CH3)2H → As2(CH3)4 + HCl
History
Jöns Jakob Berzelius coined the name kakodyl (later changed to cacodyl) for the dimethylarsinyl radical, (CH3)2As, from the Greek kakodes (evil-smelling) and hyle (matter).
It was investigated by Edward Frankland and Robert Bunsen and is considered one of the earliest organometallic compounds ever discovered. It was originally made from arsenic distilled with potassium acetate.
In Bunsen's words "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 noticeable".
Work on cacodyl led Bunsen to the postulation of methyl radicals.
Use
Cacodyl was used to prove the radical theory of Berzelius, which resulted in a wide use of cacodyl in research laboratories. After the radical theory was established, the interest in the toxic substance with the awful smell decreased. During World War I the use of cacodyl as poison gas was considered, but it was never used in the war. The inorganic chemists discovered the properties of cacodyl as a ligand for transition metals.
References
- Berzelius, J. J. (1839). Jahresberichte über die Fortschritte der physischen Wissenschaften. 18: 487.
{{cite journal}}: Missing or empty|title=(help)
- John H. Burns and Jürg Waser (1957). "The Crystal Structure of Arsenomethane". J. Am. Chem. Soc. 79 (4): 859–864. doi:10.1021/ja01561a020.
- Seyferth, Dietmar (2001). "Cadet's Fuming Arsenical Liquid and the Cacodyl Compounds of Bunsen". Organometallics. 20 (8): 1488–1498. doi:10.1021/om0101947.