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Dimethylmercury

Dimethylmercury
Skeletal formula of dimethylmercury with all hydrogens added
Spacefill model of dimethylmercury
Names
IUPAC name
Dimethylmercury
Identifiers
593-74-8 N
3D model (Jmol) Interactive image
3600205
ChEBI CHEBI:30786 YesY
ChemSpider 11155 YesY
ECHA InfoCard 100.008.916
EC Number 209-805-3
25889
MeSH dimethyl+mercury
PubChem 11645
RTECS number OW3010000
UNII C60TQU15XY YesY
UN number 3383
Properties
HgC
2H
6
Molar mass 230.66 g mol−1
Appearance Colorless liquid
Odor Sweet
Density 2.961 g mL−1
Melting point −43 °C (−45 °F; 230 K)
Boiling point 93 to 94 °C (199 to 201 °F; 366 to 367 K)
1.543
Thermochemistry
57.9–65.7 kJ mol−1
Hazards
GHS pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H300, H310, H330, H373, H410
P260, P264, P273, P280, P284, P301+310
Very Toxic T+ Dangerous for the Environment (Nature) N
R-phrases R26/27/28, R33, R50/53
S-phrases (S1/2), S13, S28, S36, S45
NFPA 704
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g., propane Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 5 °C (41 °F; 278 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Dimethylmercury ((CH3)2Hg) is an organomercury compound. This colorless liquid is one of the strongest known neurotoxins. It is described as having a slightly sweet smell, although inhaling enough vapor to detect its odor would be hazardous.

The compound was one of the earliest organometallics reported, reflecting its considerable stability. It is formed by treating sodium amalgam with methyl halides:

It can also be obtained by alkylation of mercuric chloride with methyllithium:

The molecule adopts a linear structure with Hg-C bond lengths of 2.083 Å.

The most striking feature of the compound is its nonreactivity toward water, whereas the corresponding organocadmium and organozinc compounds hydrolyze rapidly. The difference reflects the low affinity of Hg(II) for oxygen ligands. The compound reacts with mercuric chloride to give the mixed chloro-methyl compound:

Whereas dimethylmercury is a volatile liquid, CH3HgCl is a crystalline solid.

Dimethylmercury currently has few applications because of the risks involved. As with many methyl-organometallics, it is a methylating agent that can donate its methyl groups to an organic molecule; however, the development of less acutely toxic nucleophiles such as dimethylzinc and trimethylaluminium, and the subsequent introduction of Grignard reagents (organometallic halides), has essentially rendered this compound obsolete in organic chemistry. It was formerly studied for reactions in which the methylmercury cation was bonded to the target molecule, forming potent bactericides; however, the bioaccumulation and ultimate toxicity of methylmercury has largely led it to be abandoned for this purpose in favor of the less toxic diethylmercury and ethylmercury compounds, which perform a similar function without the bioaccumulation hazard.


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