Ethylmercuric chloride

Ethylmercuric chloride [107-27-7] M 265.1, m 193-194°. Mercuric chloride can be removed by suspending ethylmercuric chloride in hot distilled water, filtering with suction in a sintered-glass crucible and drying. Then crystd from ethanol and sublimed under reduced pressure. It can also be crystd from water. 

Methylmercuric chloride (h/Jj 20-25), ethylmercuric chloride (h/ f 25-30), phenylmercuric chloride (h/ f 35-40), dimethylmercury (h/ f 65-70) and diphenylmer-cury (h/Jf 75-80) appeared as violet zones on a pale yellow to pale green background. 

Fig. 1 Reflectance scan of a chromatogram track with 30 ng substance (calculated as Hg) per chromatogram zone 1 = methylmercuric chloride, 2 = ethylmercuric chloride, 3 = phenyl-mercuric chloride, 4 = dimethylmercury, 5 = diphenylmercury.

The degradation of phenylmercuric acetate to benzene, methylmercuric chloride to methane, and ethylmercuric chloride to ethane and Hg + is apparently carried out by different enzymes from the plasmid-carrying Escherichia coli strain K12 (R831) (Schottel 1978) and Pseudomonas sp. Resistance to organic mercury compounds has also been found in clinical isolates of nontuber-culous, rapidly growing mycobacteria (Steingrube et al. 1991) and can present a challenge in the clinical environment. 

Ethyl maltol, 12 49 Ethylmercuric chloride, 22 25 Ethyl-n-butylamine, 2 538t... 

Reactions. Thiosalicylic acids reacts with ethylmercuric chloride in alcohol and in the presence of sodium hydroxide to yield sodium ethyhnercurithiosalicylate [54-64-8] (thimerosal Merthiolate, EH Lilly and Company) (63) (eq. 12). 

In solvent DMSO, the rate of reaction (17) (R = Me, X = Cl) was too fast to follow, but using the mixture DMSO-dioxan (1 9 v/v) at 24.7 °C, rate coefficients for the substitution of the gold(I) complex by several alkylmercuric salts were obtained. It was found that in this mixed solvent, reaction (17) followed first-order kinetics, first-order in the gold(I) complex and zero-order in the alkylmercuric salt. Furthermore, the first-order rate coefficient had the same value no matter what alkylmercuric salt was used (methylmercuric acetate, methylmercuric chloride, methylmercuric bromide, and ethylmercuric chloride were the salts used). At 24.7 °C, the first-order rate coefficient has the value 0.0083 sec-1, with a standard deviation of 0.0006 sec-1. 

The commercial production of mercury fungicides from organolead compounds is based on patents by Kharasch 184,185). The mercury compounds are used in the disinfection of seeds and grains. Typical compounds are ethylmercuric chloride, ethylmercuric sulfate, ethyl-mercuric phosphate, phenylmercuric acetate, and compounds derived from substituted phenols and ureas. The manufacture of these compounds was reviewed by Whelen in 1957 310>. The alkylation reaction is a general reaction, and a number of additional patents has been issued on methods similar to Whelen s. A representative equation is ... 

The mercuric chloride is generally ball-milled with talc as an inert material, and then tetraethyllead is slowly added. Usually, the commercial product contains approximately 2% ethylmercuric chloride. The dilute product, as manufactured, is sold as a seed disinfectant. DuPont is the leading manufacturer. 

However, for the synthesis of alkenylmercuric salts, one difficulty was encountered as mercuric acetate also reacted with the residual double bond. Fortunately, cyclohexene with mercuric acetate in tetrahydrofuran gave only 8 % reaction after 42 h1951. Thus, 2-(4-cyclohexenyl)-ethylmercuric chloride was obtained in 94% isolated yield via hydroboration-mercuration sequence of 4-vinyl cyclohexene (Eq. 123) 192). 

SYNS CERESAN EMC ETHYLMERCURIC CHLORIDE ETHYLMERCURY CHLORIDE GANOZAN GRANOSAN... 

Pirker C, Moslinger T, Wantke F, Gotz M, Jarisch R. Ethylmercuric chloride the responsible agent in thimerosal hypersensitivity. Contact Dermatitis 1993 29(3) 152-4. 

Mercury ethyl benzyl is prepared from ethyl magnesium bromide and benzyimercuric chloride. It is an oil, decomposing on long keeping into mercury diethyl and mercury dibenzyl. When treated with thallic chloride it yields thallous chloride, ethylmercuric chloride, benzyl-mercuric chloride, and benzaldehyde. ... 

Thimerosal is prepared by the interaction of ethylmercuric chloride, or hydroxide, with thiosalicylic acid and sodium hydroxide, in ethanol (95%). 

Organic Mercury. Limited information was located regarding respiratory effects in humans after oral exposure to organic mercury. Two boys who died after eating meat from a hog that had eaten seed treated with ethylmercuric chloride developed bronchopneumonia and edematous alveolitis, and required artificial ventilation (Cinca et al. 1979). Bronchopneumonia was also identified as the cause of death in four adults and one infant who died as the result of methylmercury poisoning in Iraq during 1972 (Al-Saleem and the Clinical Committee on Mercury Poisoning 1976). It is unclear whether these respiratory effects were the result of direct effects on the respiratory system or were secondary to other effects. 

Derivation Reaction between ethylmercuric chloride and thiosalicylic acid in alcoholic sodium hydroxide. 

Various organomercury compounds (e.g. ethylmercuric chloride, methyl mercury, dimethyl mercury), found as environmental contaminants or used as fungicides, are irreversible neurotoxins. Damage cell bodies of neurones in the dorsal root ganglia and brain. See also mercury. 

Dichloro(ethyl)arsine 485 Diethylmercury (150 g) is dropped into ice-cooled arsenic trichloride (150 g) a strongly exothermic reaction occurs and crystals separate. The mixture is finally heated for 0.5 h on a water-bath, then treated with anhydrous ether, filtered from the precipitated ethylmercuric chloride, and freed from ether. By repeated fractional distillation the dichloro(ethyl)arsine is separated from the excess of arsenic trichloride the yield of the former, b.p. 145-150°/760 mm, is 90 g. 

SYNONYMS Synonyms vary depending upon the specific (organo) alkyl mercury compound (dimethylmercury) mercury dimethyl (diethylmercury) mercury diethyl (ethylmercuric chloride) chloroethylmercury, ceresan. 

Triethylbismuthine, ( 2115)361, has been obtained by the action of ethyl iodide on potassium-bismuth alloy, and from bismuth bromide and zinc diethyl. It is a fuming oil, distilling unchanged at 107° C. at 79 mm., and exploding when heated in air at ordinary pressures. Its density is 1 82. Its solubihty and behaviour towards halogens is similar to that of the methyl compound. Evaporation of its ether solution in the presence of air leads to the formation of bismuth hydroxide, and if the solution be saturated with hydrogen sulphide, bismuth sulphide separates. If to a warm dilute alcoholic solution of triethylbismuthine a sinular solution of mercuric chloride is added, a precipitate of mercurous chloride is thrown down but if the order of addition is reversed, ethylmercuric chloride and ethyldichlorobismuthine are produced ... 

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