3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||230.66 g mol−1|
|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)|
Refractive index (nD)
Std enthalpy of
|57.9–65.7 kJ mol−1|
|GHS signal word||DANGER|
|H300, H310, H330, H373, H410|
|P260, P264, P273, P280, P284, P301+310|
|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).
|what is ?)(|
Dimethylmercury ((CH3)2Hg) is an organomercury compound. A highly volatile, reactive, flammable, and colorless liquid, dimethylmercury is one of the strongest known neurotoxins, with a quantity of less than 0.1 mL capable of inducing severe mercury poisoning, and is easily absorbed through the skin. Dimethylmercury is capable of permeating many materials, including plastic and rubber compounds. It has a slightly sweet odor, although inhaling enough of the chemical to notice this would be hazardous.
The acute toxicity of the compound was demonstrated by the death of heavy metal chemist Karen Wetterhahn, who died 10 months after a single exposure permeated through her disposable latex gloves.
Synthesis, structure, and reactions
- HgCl2 + 2 LiCH3 → Hg(CH3)2 + 2 LiCl
The molecule adopts a linear structure with Hg-C bond lengths of 2.083 Å.
An interesting feature of this compound is its unreactivity toward water and the fact that it reacts with mineral acids at a significant rate only at elevated temperatures, 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:
- (CH3)2Hg + HgCl2 → 2 CH3HgCl
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.
In toxicology, it was formerly used as a reference toxin. It has also been used to calibrate NMR instruments for detection of mercury, although diethylmercury and less toxic mercury salts are now preferred.
Dimethylmercury is extremely toxic and dangerous to handle. Absorption of doses as low as 0.1 mL can result in severe mercury poisoning. The risks are enhanced because of the high vapor pressure of the liquid.
Permeation tests showed that several types of disposable latex or polyvinyl chloride gloves (typically, about 0.1 mm thick), commonly used in most laboratories and clinical settings, had high and maximal rates of permeation by dimethylmercury within 15 seconds. The American Occupational Safety and Health Administration advises handling dimethylmercury with highly resistant laminated gloves with an additional pair of abrasion-resistant gloves worn over the laminate pair, and also recommends using a face shield and working in a fume hood.
Dimethylmercury is metabolized after several days to methylmercury. Methylmercury crosses the blood–brain barrier easily, probably owing to formation of a complex with cysteine. It is eliminated from the organism slowly, and therefore has a tendency to bioaccumulate. The symptoms of poisoning may be delayed by months, resulting in cases in which a diagnosis is ultimately discovered, but only at the point in which it is too late for an effective treatment regimen to be successful.
The toxicity of dimethylmercury was highlighted with the death of Karen Wetterhahn, a professor of chemistry at Dartmouth College, in 1997. Professor Wetterhahn specialized in heavy metal poisoning. After she spilled a few drops of this compound on her latex glove, the barrier was compromised, and within minutes it was absorbed into her skin. It circulated through her body and accumulated in her brain, resulting in her death ten months later. This accident is a common toxicology case-study and directly resulted in improved safety procedures for chemical-protection clothing and fume use, which are now called for when any exposure to such severely toxic and/or highly penetrative substances is possible (e.g., in chemical munitions stockpiles and decontamination facilities).
- "dimethyl mercury - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 10 March 2012.
- Agency for Toxic Substances and Disease Registry (March 1999). "Toxological profile for mercury". United States Department of Health and Human Services, Public Health Service. Retrieved 16 August 2014.
- Holleman, A. F.; Wiberg, E. (2001). Inorganic Chemistry. San Diego: Academic Press. ISBN 0-12-352651-5.
- 1948-, Crabtree, Robert H., (2005). The organometallic chemistry of the transition metals (4th ed.). Hoboken, N.J.: John Wiley. p. 424. ISBN 0471662569. OCLC 61520528.
- Baughman, George L.; Or.), National Environmental Research Center (Corvallis (1973). Chemistry of organomercurials in aquatic systems. For sale by the Supt. of Docs., U.S. Govt. Print. Off. pp. 34–40.
- Pubchem. "Methylmercury chloride". pubchem.ncbi.nlm.nih.gov. Retrieved 2018-09-16.
- O'Halloran, T. V.; Singer, C. P. (1998-03-10). "199Hg Standards". Northwestern University. Retrieved 2012-05-24.
- Hoffman, R. (2011-08-01). "(Hg) Mercury NMR". Jerusalem: The Hebrew University. Retrieved 2012-05-24.
- "Delayed Toxic Syndromes" (pdf). Terrorism by Fear and Uncertainty. ORAU.
- "OSHA Safety Hazard Information Bulletin on Dimethylmercury". Safety and Health Information Bulletins (SHIBs), 1997-1998. OSHA. 1991-02-15.
- Nierenberg, David W.; Nordgren, Richard E.; Chang, Morris B.; Siegler, Richard W.; Blayney, Michael B.; Hochberg, Fred; Toribara, Taft Y.; Cernichiari, Elsa; Clarkson, Thomas (1998). "Delayed Cerebellar Disease and Death after Accidental Exposure to Dimethylmercury". New England Journal of Medicine. 338 (23): 1672–1676. doi:10.1056/NEJM199806043382305. PMID 9614258.
- Cotton, S. (October 2003). "Dimethylmercury and Mercury Poisoning. The Karen Wetterhahn story". Molecule of the Month. Bristol University.
- "The Karen Wetterhahn story". Retrieved 1 September 2014.