diethylmercury
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424699118
| Name = Diethylmercury
| ImageFile = Diethyl mercury.svg
| IUPACName = diethylmercury
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 627-44-1
| EINECS = 211-000-7
| MeSHName = C007378
| RTECS =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 11814
| PubChem = 12318
| SMILES = CC[Hg]CC
| InChI = 1/2C2H5.Hg/c2*1-2;/h2*1H2,2H3;/rC4H10Hg/c1-3-5-4-2/h3-4H2,1-2H3
| InChIKey = SPIUPAOJDZNUJH-KFYQOLPSAK
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/2C2H5.Hg/c2*1-2;/h2*1H2,2H3;
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = SPIUPAOJDZNUJH-UHFFFAOYSA-N
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 323TG9BTE8
}}
|Section2={{Chembox Properties
| Formula = {{Chem|C|4|H|10|Hg}}
{{Chem|({{Chem|C|2|H|5}})|2|Hg}}
| MolarMass = 258.71 g/mol
| Appearance = Colorless liquid
| Density = 2.446 g/ml
| Solubility = Insoluble
| SolubleOther = Ethers, hydrocarbons, THF
| MeltingPtC = -45
| BoilingPtC = 156 to 157
| BoilingPt_notes =
| Odor = Sweet
}}
|Section3={{Chembox Structure
| MolShape =
}}
|Section7={{Chembox Hazards
| ExternalSDS =
| MainHazards = Flammable, extremely toxic
| FlashPt = N/A
| GHSPictograms = {{GHS06}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|300+310+330|373|410}}
| PPhrases = {{P-phrases|260|262|264|270|271|273|280|284|301+310|302+350|304+340|310|314|320|321|322|330|361|363|391|403+233|405|501}}
}}
}}
Diethylmercury is a flammable, colorless liquid, and one of the strongest known neurotoxins. This organomercury compound is described as having a slightly sweet smell, though inhaling enough fumes to notice this would be hazardous.{{Cite web|url=http://www.chemicalbook.com/ChemicalProductProperty_EN.aspx?CBNumber=CB7165894|title=Diethyl Mercury | 627-44-1|access-date=2009-01-28|archive-date=2018-10-27|archive-url=https://web.archive.org/web/20181027021631/https://www.chemicalbook.com/ChemicalProductProperty_EN.aspx?CBNumber=CB7165894|url-status=dead}}
This chemical can cross the blood–brain barrier, causing permanent brain damage. It is, however, considerably less toxic than dimethylmercury.
The resulting (CH3CH2)2Hg is a dense liquid (2.466 g/cm3) that boils at 57 °C at 16 torr. This extremely toxic compound is slightly soluble in ethanol and soluble in ether.
Synthesis
Diethylmercury can be obtained from the reaction between ethylmagnesium bromide and mercury(II) chloride.{{Cite book|last=Brauer|first=Georg|url=https://www.worldcat.org/oclc/310719490|title=Handbuch der präparativen anorganischen Chemie Bd. 2.|others=Baudler, Marianne|date=1975 |isbn=978-3-432-87813-3|edition=3rd|location=Stuttgart|pages=1063|oclc=310719490}}
:2 C2H5MgBr + HgCl2 → Hg(C2H5)2 + MgBr2 + MgCl2
Other methods are also known.{{Cite book|last=Kolbe|first=Hermann|title=Ausführliches Lehrbuch der organischen Chemie, Volume 2|year=1860|pages=964|author-link=Hermann Kolbe|url=https://books.google.com/books?id=-qU5AAAAcAAJ&pg=PA964}}
See also
References
{{Mercury compounds}}
{{DEFAULTSORT:Diethyl Mercury}}
Category:Organomercury compounds