115-09-3

Usage

Chemical Properties

white crystals or powder

Uses

Different sources of media describe the Uses of 115-09-3 differently. You can refer to the following data:
1. industrial and agricultural uses of the compound and its industrial production have generally been abandoned because of its high toxicity. Methylmercury remains of considerable concern, however, because of its continuous formation in the environment. In the aquatic environment, elemental mercury is first oxidized to the mercuric mercury ion (Hg2+ ), which may then become methylated to form methylmercury compounds, either by chemical or microbiologically catalyzed reactions. Methylmercury is accumulated by fish and marine mammals and attains its highest concentrations in large predatory species at the top of the aquatic and marine food chains. By this means, methylmercury enters the human diet. Thus, minimization of environmental mercury contamination is imperative.
2. Methylmercury(II) chloride is used as a precursor for the preparation of methyl mercury acetate. It is used as a specific reagent (electron stain) for sulfhydryl groups in biological materials like protein as well as demonstration in electron microscopy.

General Description

White microcrystals or crystals.

Air & Water Reactions

Aqueous solutions at a concentration of 0.25 mg / mL are stable for 3 weeks in the dark at room temperature. Aqueous 0.0001 M solutions show no degradation after 17.1 hours of midday sunlight. High intensity UV irradiation of solutions causes decomposition .

Reactivity Profile

METHYLMERCURY(II) CHLORIDE may be sensitive to light.

Fire Hazard

Flash point data for METHYLMERCURY(II) CHLORIDE are not available; however, METHYLMERCURY(II) CHLORIDE is probably nonflammable.

Safety Profile

Poison by ingestion, intramuscular, intravenous, and intraperitoneal routes. Questionable carcinogen with experimental carcinogenic and teratogenic data. Human mutation data reported. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of Cland Hg. See also MERCURY COMPOUNDS.

Carcinogenicity

A number of authors have reported carcinogenic effects in rats and mice exposed orally to methylmercury. An association between methylmercury exposure and renal adenocarcinoma was shown in male mice, but no increase in tumor incidence was detected in rats. These findings are supported by reports on methylmercury-induced degeneration of DNA, and inhibition of the formation of the mitotic spindle.Intoxications with alkoxialkyl or aryl compounds are similar to intoxications with inorganic mercury compounds, as these organomercurials are relativelyunstable. Alkylmercury compounds, such as methylmercury, result in a different syndrome due to the stability of the mercury–methyl binding. The earliest symptoms in adults are paresthesias in the extremities and the face, particularly around the mouth. Later on, disturbances occur inthe motor functions, resulting in ataxia and dysphasia. The visual field is decreased, and, in severe cases, may result in total blindness. These symptoms were observed in large-scale poisonings caused by methylmercury.

Purification Methods

Recrystallise it from absolute EtOH (20mL/g). at 206nm ( 1.37). [See EtHgCl above; Breitinger et al. J Organomet Chem 256 217 1983,max Slotta et al. J Prakt Chem 120 249 1929, Waugh et al. J Phys Chem 59 395 1955, Beilstein 16 IV 1729.]

InChI:InChI=1/CH3.ClH.Hg/h1H3;1H;/q;;+1/p-1/rCH3ClHg/c1-3-2/h1H3

Upstream product

• 1600-27-7 mercury(II) diacetate 
• 593-74-8 dimethylmercury 
• 75-24-1 trimethylaluminum 
• 75-16-1 methylmagnesium bromide 
• 594-27-4 tetramethylstannane 
• 75-74-1 Tetramethylblei-(IV) 
• 143-36-2 methylmercury(II) iodide 
• 917-65-7 methylaluminum dichloride 
• 1184-58-3 dimethylaluminum chloride 
• 35787-71-4 thianthrene cation radical perchlorate 
• 2288-13-3 1-methylsilatrane 
• 917-64-6 methyl magnesium iodide 
• 104923-33-3 mercury(I) chloride 
• 753-73-1 dimethyltin dichloride 

Downstream Products

• 593-74-8 dimethylmercury 
• 594-27-4 tetramethylstannane 
• 17019-36-2 (benzenethiolato)methylmercury(II) 
• 639-58-7 triphenyltin chloride 
• 1278-83-7 bis(cyclopentadienyl)methyltitanium(IV) chloride 
• 21392-61-0 methyl phenyl mercury 
• 50281-55-5 HgCl₂(P(CH₃)3)2 
• 88722-08-1 CH₃HgSe(C₆H₅) 
• 14494-85-0 HgCl₂(triphenylphosphine)2 
• 51312-24-4 mercury(II) chloride 
• 211821-27-1 {(μ-SPh)6(ZnCl)4}(2-) 

Relevant academic research and scientific papers

Mechanistic Studies into the Sn/Hg Exchange Reaction of 1,2-Fc(PPh2)(SnMe3) with HgCl2: Competitive Sn-Me over Sn-Fc Cleavage in Noncoordinating Solvents

Tin-mercury exchange represents one of the most versatile and cleanest routes to arylmercuric halides. We found that reaction of the ferrocenylstannane 1,2-Fc(PPh2)(SnMe3) (1) with HgCl2 in acetone results in the unexpected spontaneous formation of 2·HgCl2, a diferrocenylmercury (Fc2Hg)-supported diphosphine chelate ligand as its HgCl2 complex. Mechanistic investigations into the generation of 2·HgCl2 reveal initial formation of an adduct of 1 with HgCl2, followed by competitive Sn-Me and Sn-Fc bond cleavage with formation of chloromercury and chlorodimethylstannyl-substituted ferrocene species. When the reaction is performed in chloroform as a noncoordinating solvent, formation of 2·HgCl2 is not observed, but instead 1,2-Fc(PPh2)(SnMe2Cl) (5) is generated as the major product. 5 is initially isolated as a complex with MeHgCl (generated as a byproduct), but the latter can be easily released by heating under high vacuum. When 5 is further reacted with 2 equiv of HgCl2 in acetone, the adduct 1,2-Fc(PPh2·HgCl2)(HgCl) (6·HgCl2) forms. An X-ray crystal structure of 6·HgCl2 shows two individual molecules that form Hg···Cl-bridged dimers, which in turn are linked by intermolecular Hg···Cl contacts to give a polymeric structure. In contrast, the equimolar reaction of 5 and HgCl2 results in initial complexation to give 5·HgCl2, which slowly transforms into the diferrocenylmercury species 2·HgCl2. These results confirm that both 1 and the byproduct 5 obtained by Sn-Me bond cleavage are competent intermediates in the formation of complex 2 in acetone. The preferential cleavage of the Sn-Me over the Sn-Fc bond in noncoordinating solvents is attributed to the presence of the diphenylphosphino group in an ortho position. These observations may have broader implications due to the formation of MeHgCl as a highly toxic and volatile byproduct and suggest that noncoordinating solvents are better avoided and extreme caution is necessary when performing Sn/Hg exchange reactions on donor-substituted substrates.

Asymmetric fluoro-alkynyl mercurials: The synthesis and solid state structures of RHgC=CCF3 (R = Ph, Fc)

The fluoro-alkynyl mercurials RHgC=CCF3 (R = Ph, Fc) have been prepared, from the respective organomercurihalides and LiC=GCF3, and are the first examples of such materials to be studied crystallographically. These studies have revea

Oxidative cleavage reactions of compounds of the type CpRuLL′R (L, L′ = CO, PPh3; R = Me, PhCH2)

The compounds CpRuLL′R (Cp = η5-C5H5; L, L′ = CO, PPh3; R = Me, PhCH2) have been prepared, some by improved routes. Alkyl cleavage reactions with halogens, hydrogen chloride, mercury(II) halides, and

Synthesis, characterization, and C-H activation reactions of novel organometallic O-donor ligated Rh(III) complexes

The synthesis and characterization of the O-donor ligated, air and water stable organometallic complexes trans- (2), and cis-(hfac-O,O) 2Rh(CH3)(py) (3), trans-(hfac-O,O)2Rh(C 6H5)(py) (4), cis-(hfac-O,O)2Rh(C 6H5)(py) (5), and cis-(hfac-O,O)2Rh(Mes)(py) (6) (where hfac-O,O = κ2-O,O-1,1,1,5,5,5- hexafluoroacetylacetonato) are reported. These compounds are analogues to the O-donor iridium complexes that are active catalysts for the hydroarylation and C-H activation reactions as well as the bis-acetylacetonato rhodium complexes, which we recently reported. The trans-complex 2 undergoes a quantitative trans to cis isomerization in cyclohexane to form 3, which activates C-H bonds in both benzene and mesitylene to form compounds 5 and 6, respectively. All of these compounds are air and water stable and do not lead to decomposition products. Complex 5 promotes hydroarylation of styrene by benzene to generate dihydrostilbene.

Syntheses of monomeric (η5-pentamethylcyclopentadienyl)platinum(IV) methyl and bromo complexes and of [hydrotris(3,5-dimethyl-1-pyrazolyl)borato]trimethylplatinum

The reaction of Cp*MgCl·THF (Cp* = C5Me5) with 1 equiv of PtMe3I and PtMe2Br2 produces Cp*PtMe3 (1) and Cp*PtMe2Br (2), respectively. Reaction of 2 with Br2 produces Cp*PtMeBr2 (3) in good yield. The structures of 2 and 3 have been determined by X-ray crystallography. Complex 2 crystallizes in the monoclinic space group, P21/m, with a = 7.017 (4) A?, b = 11.573 (4) A?, c = 8.496 (3) A?, β = 98.59 (3)°, Z = 2, V = 682.1 A?3, R = 0.067, and Rw = 0.081. Complex 3 also crystallizes in the monoclinic space group, P21/m, with a = 7.147 (2) A?, b = 12.171 (4) A?, c = 8.617 (2) A?, β = 113.77 (2)°, Z = 2, V = 685.9 A?3, R = 0.036, and Rw = 0.053. The molecules reside on mirror planes and are monomeric pseudotetrahedral Pt(IV) complexes with "piano stool" type geometries and η5-Cp* groups. Both molecules have Br atoms on the mirror. This leads to a disorder of the Me and the second Br positions in complex 3. The average Pt-C(Cp*) bond length is 2.25 (7) A? in 2 and 2.22 (4) A? in 3. The Pt-C(Me) and Pt-Br bond lengths in 2 are 2.07 (2) and 2.498 (2) A?, respectively. The ordered Pt-Br bond length in 3 is 2.496 (2) A?. Treatment of 1 with halogens results in the cleavage of the Pt-Cp* bond. The reaction of PtMe3I with KTp* (Tp* = [HB-(3,5-dimethylpyrazolyl)3]-) in thf gives Tp*PtMe3 (4) in almost quantitative yield. The reaction of 4 with Br2 brominates the 4-position of the pyrazolyl ring only.

Evidence for Electron Transfer in Reactions of Thianthrene Cation Radical with Dialkylmercurials

Reactions of dialkylmercurials (R2Hg) with thianthrene cation radical perchlorate (Th.+ClO4-) in acetonitrile solution have been studied in quantitative detail.Evidence was obtained from reactions of MeHgR (R = Et, i-Pr, tBu) that reaction begins with electron transfer rather than with electrophilic cleavage of an alkyl-mercury bond.That is, each reaction gave MeHg+ and R., diagnostic of the formation and decomposition of MeHgR.+, rather than 5-methylthianthreniumyl perchlorate (1a), which would have been diagnostic of electrophilic displacement of the least hindered group (Me).The radicals R. either were trapped at the sulfur atom of Th.+ to form a 5-alkylthianthreniumyl perchlorate (Et., 1b) and at the ring positions of Th.+ to form 1- and 2-alkylthianthrenes (Et., i-Pr.) or were oxidized to the cations R+ (Et., i-Pr., and t-Bu.).Products of R+ were obtained, after workup with 4 M aqueous LiCl, as alkene, ROH, RNHCOCH3 and RCl.These reactions had the stoichiometric ratio of reactants 2Th.+ClO4-/MeHgR.Reactions of symmetrical R2Hg sometimes followed this stoichiometry (R = Me, Et, Bu) and led to RHg+ and 5-R-thianthreniumyl perchlorates (1a,b,e).Other R2Hg (R = t-Bu, benzyl, allyl) underwent oxidation by 4 equiv of Th.+ClO4-.Di-tert-butyl- and dibenzylmercury gave products derived entirely from the respective cation, R+.Diallylmercury gave some of the sulfonium product, 5-allylthianthreniumyl perchlorate (1g).None of the reactions with R = i-Pr, t-Bu, and benzyl led to the isolation of a thianthreniumyl perchlorate (i.e., 1c,d,f).Oxidations at the 4:1 molar ratio produced Hg(ClO4)2, which formed a partly insoluble complex (2) with thianthrene having the composition Th3Hg(ClO4)2.This product could be isolated if removed before workup treatment with aqueous 4 M LiCl, which, otherwise caused its decomposition into its components.The complex 2 was also prepared directly from reaction of Th with Hg(ClO4)2 in acetonitrile.Oxidation of benzylmercuric chloride by Th.+ClO4- in methylene chloride solution also occurred quantitatively, giving benzyl chloride, 1- and 2-benzylthianthrene, and a mixture of dibenzylthianthrenes.Oxidation of t-BuHgCl in acetonitrile solution led to a quantitative mixture of isobutene, t-BuOH, and t-BuNHAc.Th.+ClO4- also oxidized metallic Hg to either Hg+ or Hg2+, depending on the amount of oxidant used.

Electrophilic cleavages in (CH3)3SnCH2M(CH3)3 (M = Sn, Ge, Si, C). 1. Product distribution

The extent to which Sn-CH2 and/or Sn-CH3 cleavage occurs in (CH3)3SnCH2M(CH3)3 (M = Sn, Ge, Si) in reactions with several electrophiles has been determined. With iodine and with

DIRECT TRANSFER OF ALIPHATIC AND AROMATIC SUBSTITUENTS FROM ORGANOSILATRANES TO MERCURY(II) SPECIES

The relative reaction rates of several silatranes (derivatives of 2,8,9-trioxa-5-aza-1-silatricyclo1,5>undecane) and HgCl2 in acetone-d6 to yield the corresponding organomercury compound are of the order of e.g., 5 * 10-1 1 mol-1 sec-1 or slightly less, a rate that is unexpectedly high compared to the essentially inert parent organotrialkoxysilanes.Thus, the apical Si-C bond of the silatrane is extraordinarily susceptible to direct electrophilic attack by mercury(II).The rates decrease in the order CH2=CH, C6H5, p-ClC6H4 > CH3 > CH3CH2, CH3CH2CH2 > C6H11, ClCH2, Cl2CH, CH3CH2O.The effects of varying the solvent and the counterions are noted, and the probable mechanism is discussed.

REACTIONS OF ORGANOMERCURY FULMINATES WITH ACETYLENE DERIVATIVES

Organomercury fulminates react with acetylene derivatives to give unstable 3-(organomercurio)isoxazoles, which isomerize to 2-cyanoenolates.These are hydrolyzed with hydrochloric acid to the corresponding enols and are cleaved by water at the double bond.With monosubstituted acetylenes, substitution at the free position by the organomercury residue is predominant.