|Jmol 3D model||Interactive image|
|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|
EU classification (DSD)
|R-phrases||R26/27/28, R33, R50/53|
|S-phrases||(S1/2), S13, S28, S36, S45|
|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. 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.
Synthesis, structure, reactions
- HgCl2 + 2 LiCH3 → Hg(CH3)2 + 2 LiCl
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:
- (CH3)2Hg + HgCl2 → 2 CH3HgCl
Dimethylmercury currently has almost no 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 related ethylmercury cation, which perform a similar function without the bioaccumulation hazard.
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.
Dimethylmercury passes through latex, PVC, butyl, and neoprene within seconds, and is very quickly absorbed through the skin. Much safety equipment used to prevent exposure to other chemicals does not provide protection from dimethylmercury.
Gloves commonly used in most laboratories and clinical settings do not provide adequate protection from dimethylmercury. 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 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 many cases in which a diagnosis was ultimately discovered, but only at the point in which it is often too late for an effective treatment regimen to be successful.
The toxicity of dimethylmercury was highlighted with the death of the inorganic chemist Karen Wetterhahn of Dartmouth College in 1997. After spilling no more than a few drops of this compound on her latex-glove, the barrier was immediately compromised and within seconds it was absorbed into the back of her hand, quickly circulating and resulting in her death ten months later. This accident is a common toxicology case-study and spurred the development of modern advanced chemical-protection clothing which is now used when any exposure to severely toxic and/or highly penetrative substances is possible (ex. 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.
- 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.
- 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.