diphenylmercury(II)
trimethyl gallium
A
methyl(diphenyl)gallium
B
dimethylmercury
Conditions | Yield |
---|---|
In neat (no solvent) (CH3)3Ga was added to freshly sublimed diphenylmercury, the suspn. was heated at 100°C in a closed vessel for 3 h, cooled to room temp. without stiring; volatiles were removed in vac. (1E-2 mbar), crystals were washed with n-hexane and dried in vac. for 2 h: elem. anal.; | A 98% B n/a |
bis(trifluoromethyl)mercury
Tetramethylblei-(IV)
A
dimethylmercury
B
methyl(trifluoromethyl)mercury
C
trimethyl(trifluoromethyl)lead
Conditions | Yield |
---|---|
In toluene absence of air and moisture; heating of PbMe4 with two-fold excess of Hg-compd. (sealed tube, 70°C, 2 weeks); gas chromy.; | A 2% B 94% C 93% |
diphenylmercury(II)
trimethyl gallium
A
dimethyl(phenyl)gallium
B
dimethylmercury
Conditions | Yield |
---|---|
In neat (no solvent) in an Schlenk flask (CH3)3Ga was added to freshly sublimed (C6H5)2Hg, the vessel was tightly closed, the suspn. was heated at 100°C for 5h, cooled to room temp.; volatiles were removed under reduced pressure (10 mbar), the residue waswashed twice with n-hexane at -70°C; elem. anal.; | A 90% B n/a |
methylmagnesium chloride
A
Ru2(C5(CH3)5)2(C5Mg4Cl4)2Mg
B
dimethylmercury
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: methylchloride; 23°C, 12 equiv of methylmagnesiumchloride; | A 85% B n/a |
[(C5H5)2Ti(C6H5)(CH3)]
methylmercury(II) chloride
A
bis(cyclopentadienyl)methyltitanium(IV) chloride
C
dimethylmercury
D
methyl phenyl mercury
Conditions | Yield |
---|---|
In [(2)H6]acetone to cold (-78 °C) soln. of Ti complex (excess) in acetone-d6 added soln. of MeHgCl in acetone-d6 under N2, stirred at -78 °C for 2h, stirred at room temp. for 6 h; monitored by NMR; | A 40% B 60% C 60% D 40% |
1-(2-hydroxyethyl)-3-methyl-(1H)-imidazole-2(3H)-selone
methylmercury(II) chloride
B
dimethylmercury
Conditions | Yield |
---|---|
In water; acetonitrile at 23℃; for 168h; Kinetics; Schlenk technique; | A 53% B n/a |
A
GLUTATHIONE
C
dimethylmercury
D
1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one
Conditions | Yield |
---|---|
Stage #1: methylmercury-L-glutathionate; 1-(2-hydroxyethyl)-3-methyl-1H-benzo[d]imidazole-2(3H)-thione In water; acetonitrile at 37℃; for 1h; Stage #2: With sodium hydrogencarbonate In water; acetonitrile at 37℃; for 5h; | A n/a B 11 mg C n/a D 40% |
Conditions | Yield |
---|---|
With sodium amalgam; acetic acid methyl ester at -5 - -3℃; |
Conditions | Yield |
---|---|
With diethyl ether; mercury dichloride |
Conditions | Yield |
---|---|
With mercury |
Conditions | Yield |
---|---|
With diethyl ether; mercury dibromide |
Conditions | Yield |
---|---|
With pyridine; copper | |
With zinc |
Conditions | Yield |
---|---|
With sodium amalgam; acetic acid methyl ester |
Conditions | Yield |
---|---|
With sodium amalgam; ethyl acetate at 10℃; | |
With sodium amalgam; acetic acid ester |
dimethylmercury
Conditions | Yield |
---|---|
With water; mercury dichloride in schwach saurer Loesung; |
dimethylmercury
Conditions | Yield |
---|---|
With pyridine; water at 30 - 40℃; Electrolysis.An einer Platinakathode; |
dimethylmercury
Conditions | Yield |
---|---|
With ammonia Electrolysis.man an der Kathode auftretenden Niederschlag sich auf Zimmertemperatur erwaermen laesst; |
dimethylmercury
Conditions | Yield |
---|---|
With sodium hydroxide; tin(ll) chloride |
dimethylmercury
Conditions | Yield |
---|---|
With sodium sulfate Electrolysis; |
dimethylmercury
Conditions | Yield |
---|---|
beim Erwaermen; |
Conditions | Yield |
---|---|
Aus einer 25prozentigen waessrigen Loesung des Acetats.Electrolysis; |
Conditions | Yield |
---|---|
Aus einer 25prozentigen waessrigen Loesung des Acetats.Electrolysis; |
Conditions | Yield |
---|---|
Aus einer 25prozentigen waessrigen Loesung des Acetats.Electrolysis; |
Conditions | Yield |
---|---|
Aus einer 25prozentigen waessrigen Loesung des Acetats.Electrolysis; |
Conditions | Yield |
---|---|
Aus einer 25prozentigen waessrigen Loesung des Acetats.Electrolysis; |
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; Schlenk technique; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; Schlenk technique; Inert atmosphere; | 100% |
dimethylmercury
[(η5-C5H4)CH2CH(η1-O)CH2OBu(n)]YbMe(tetrahydrofuran)
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: Hg; (vac.); refluxed for 60 h; decanted, crystd. by slow diffusion of hexane vapor into the soln.; elem. anal.; | 98% |
Conditions | Yield |
---|---|
In dichloromethane stirred at room temp. for 24 h; evapd. in vac., recrystd. (CH2Cl2, 5°C), filtered, dried in vac., elem. anal.; | 91% |
dimethylmercury
tetra-n-propylammonium carbonyldichloromethylplatinate(II)
Conditions | Yield |
---|---|
In dichloromethane byproducts: Hg; addn. of stoich. amt. of Hg-compd. to Pt-complex, standing (overnight); treatment with charcoal, filtration, concn., crystn. on Et2O addn.; elem. anal.; | 91% |
phenylpentacarbonylmanganese(I)
dimethylmercury
Conditions | Yield |
---|---|
In toluene byproducts: Hg, benzene; reflux, 1 h; elem. anal.; | 82% |
[Ir(acetylacetonate-C3)(η2-O,O-acetylacetonate)2(H2O)]
dimethylmercury
[Ir(μ-acac-O,O,C3)(acac-O,O)(CH3)]2
Conditions | Yield |
---|---|
In methanol (Schlenk), dimethylmercury was added to a soln. of complex in methanol, the flask was sealed, placed in a 60°C oil bath for 2 h, cooled to room temp.; the soln. was vac.-transferred, loaded on a silica gel column, eluted with THF; elem. anal; | 80% |
Conditions | Yield |
---|---|
With sodium bromide In acetonitrile Me2Hg in CH3CN added to Fe(phen)3(ClO4)3 in CH3CN at 20°C under Ar and soln. stirred for 2 h, drop water added and Fe(II) complex filtered, filtrate dried with MgSO4 and treated NaBr; | A n/a B 78% |
dimethylmercury
thianthrenium tetrafluoroborate
5-methylthianthrenyliumyl tetrafluoroborate
Conditions | Yield |
---|---|
In acetonitrile | 76% |
tris(di-tert-butyphosphino)gallane
dimethylmercury
Quecksilber-bis-(di-tert.-butyl-phosphid)
Conditions | Yield |
---|---|
In toluene byproducts: {Me2Ga(μ-t-Bu2P)}2; excess of Me2Hg was added to frozen soln. of Ga compd. at 77 K and mixt. was slowly warmed to room temp.; volatiles were removed under vac., residue recrystd. from hexane at -30°C; | 76% |
cis-[PdCl2(CNC6H4OMe-p)2]
dimethylmercury
Conditions | Yield |
---|---|
With P(C6H5)3 In benzene byproducts: MeHgCl; addn. of slight excess of HgMe2 to Pd-complex, stirring for 7-8 h, addn.of stoich. amt. of PPh3, 15 min; filtration (charcoal), concn. (reduced pressure), pptn. on Et2O addn., filtration, washing (ether), drying (vac.), sublimation off of MeHgCl (80-100°C, 0.01 Torr), repptn. from CH2Cl2 with Et2O; elem. anal.; | 75% |
dimethylmercury
mercury(II) selenocyanate
methylmercury selenocyanate
Conditions | Yield |
---|---|
In not given metathesis reaction; elem. anal.; | 75% |
Conditions | Yield |
---|---|
In dichloromethane stirred for 48 h; evapd. in vac., dissolved in CH2Cl2 at room temp., pptd (petroether), elem. anal.; | 71% |
dimethylmercury
tungsten(VI) chloride
monomethyltungsten(VI) pentachloride
Conditions | Yield |
---|---|
In dichloromethane byproducts: MeHgCl; Ar-atmosphere; dropwise addn. of equimolar amt. of HgMe2 to WCl6 (-45°C, stirring), standing for 1 h; addn. of cold pentane (-45°C), filtration off of MeHgCl, evapn. (-20°C), washing (pentane, -20°C), recrystn. (CH2Cl2/pentane=1:5, -40°C, 1 week); elem. anal.; | 66% |
molybdenum(V) chloride
dimethylmercury
1,2-bis-(diphenylphosphino)ethane
Conditions | Yield |
---|---|
In dichloromethane byproducts: HgCl2; dry Ar and oxygen-free atmosphere, dry and degassed solvents; addn. of CH2Cl2 soln. of HgMe2 to soln. of MoCl5 in CH2Cl2 at -45°C, stirring (5 h), filtration of react. mixt. onto dppe in CH2Cl2 at -45°C, stirring (2 h); addn. of pentane, filtration, washing (pentane) at -35°C, drying under vac.; elem. anal.; | 66% |
all-trans-[Ru(CO)2(PMe2Ph)Cl2]
dimethylmercury
cct-(PhMe2P)2Ru(II)(CO)2Cl2
Conditions | Yield |
---|---|
In acetone N2-atmosphere; excess HgMe2, 313 K, 4 h; solvent removal (reduced pressure), chromy. (Al2O3, CHCl3), recrystn. (light petroleum); elem. anal.; | A n/a B 66% |
N,N'-Bis(trifluoromethylsulfonyl)sulfur diimide
dimethylmercury
Conditions | Yield |
---|---|
In dichloromethane stirred at room temp. for 48 h; solvent removed, cooled to -15°C, filtered, dried in vac., elem.anal.; | 62% |
Conditions | Yield |
---|---|
In not given byproducts: HgCH3Cl; Pd-complex was reacted with HgMe2 for 7 h, AsPh3 was added, stood for 12 h; sublimated to eliminate HgMeCl, dissolved in C6H6, EtOH was added, concd., stored at -20°C; elem. anal.; | 60% |
Trifluoromethylsulfonyliminosulfinyl dichloride
dimethylmercury
A
Dimethylschwefel-(trifluormethylsulfonyl)imid
Conditions | Yield |
---|---|
In dichloromethane for 48h; Ambient temperature; | A 57% B n/a |
tungsten oxytetrachloride
dimethylmercury
Conditions | Yield |
---|---|
With (C6H5)2PCH2CH2P(C6H5)2 In dichloromethane; pentane byproducts: MeHgCl; Ar-atmosphere; slow addn. of HgMe2 to suspn. of equimolar amt. of W-compd. (in CH2Cl2/pentane=2:1) at -80°C, stirring (-80°C, 1 h), filtration off of MeHgCl, evapn., stirring with pentane (-78°C), addn. of dppe; | 55% |
Conditions | Yield |
---|---|
In tetrahydrofuran reflux, 1 h; evapn. in vac., extn. (acetone), crystn. from CHCl3; | 50% |
cis-[bis(cyclohexylisocyanide)dichloropalladium(II)]
dimethylmercury
trans-[PdCl(C(NC6H11)CMeNC6H11)(PPh3)2]
Conditions | Yield |
---|---|
With P(C6H5)3 In benzene byproducts: MeHgCl; treatment of Pd-complex with HgMe2 (90 min), then addn. of PPh3; repptn. (CH2Cl2/hexane); elem. anal.; | 50% |
dimethylmercury
thianthrene cation radical perchlorate
A
thianthrene-5-oxide
B
methylmercury(II) chloride
C
5-Methylthianthreniumyl perchlorate
D
Thianthrene
Conditions | Yield |
---|---|
With lithium chloride In acetonitrile Product distribution; Mechanism; other dialkylmercurials, other thianthren cation radical salt, other solvent; | A 0.65% B 42.5% C 38.1% D 48.9% E n/a |
silver tetrafluoroborate
dimethylmercury
diphenylchloromethane
A
1,1-Diphenylmethanol
B
1,1'-ethylidenebis-benzene
C
methylmercury(II) bromide
Conditions | Yield |
---|---|
With potassium bromide In nitromethane byproducts: N-(diphenylmethyl)acetamide; Ar atmosphere and absence of light and moisture; addn. of AgBF4 in nitromethane to soln. of alkylmercury, portionwise addn. of Ph2CHCl in nitromethane (20°C, TLC monitoring), washing with soln. of KBr; TLC; | A 47% B 35% C 30% |
With potassium bromide In acetonitrile byproducts: N-(diphenylmethyl)acetamide; Ar atmosphere and absence of light and moisture; addn. of AgBF4 in MeCNto soln. of alkylmercury, portionwise addn. of Ph2CHCl in MeCN (20°C, TLC monitoring), pouring into soln. of KBr; extn. (CH2Cl2), TLC; | A 47% B 35% C 30% |
Dimethylmercury is most often used in toxicology experiments as a fixed point of reference due to its extreme toxicity. It has also been used to calibrate NMR instruments for detection of mercury, although less toxic mercury salts are preferred.
1. | dnd-mmo-omi 600 mg/L | NATUAS Nature. 257 (1975),422. | ||
2. | oth-mus:oth 25 mg/L | MUREAV Mutation Research. 17 (1973),93. |
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