506-82-1

Basic information

• Product Name: DIMETHYLCADMIUM
• Synonyms: (CH3)2Cd;DIMETHYLCADMIUM;CADMIUM DIMETHYL;Dimethylcadmiumelecgrcolorlessliq;Dimethylcadmiuminhexane;CADMIUM DIMETHYL 95%;Dimethylcadmium,elec.gr.(99.995+%-Cd)PURATREM;Dimethylcadmium,min.97%
• CAS NO: 506-82-1
• Molecular Formula: C₂H₆Cd
• Molecular Weight: 142.48
• EINECS: 208-055-4
• Product Categories: metal alkyl;ALD Precursors
• Mol File: 506-82-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: -4,5°C
• Boiling Point: 105,5°C
• Flash Point: -18°C
• Appearance: colorless/liquid
• Density: 1,986 g/cm3
• Refractive Index: nD 1.5488
• Sensitive: moisture sensitive
• CAS DataBase Reference: DIMETHYLCADMIUM(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYLCADMIUM(506-82-1)
• EPA Substance Registry System: DIMETHYLCADMIUM(506-82-1)

Safety Data

• Statements: 17-20/21/22
• Safety Statements: 7/8-16-23-36/37/39-45
• RIDADR: 2845
• TSCA: Yes
• HazardClass: 4.2
• PackingGroup: I
• Hazardous Substances Data: 506-82-1(Hazardous Substances Data)

Usage

Uses

In organic synthesis; as polymerization catalyst.

Safety Profile

Confirmed human carcinogen. Contact with air produces the friction-sensitive explosive dimethyl cadmium peroxide. Explodes when heated above 15OOC. Ignition may occur on contact with air if the surface area is large. See also CADMIUM COMPOUNDS.

InChI:InChI=1/2CH3.Cd/h2*1H3;/rC2H6Cd/c1-3-2/h1-2H3

Synthetic route

tin(IV) iodide + bis(trifluoromethyl)cadmium*glyme → trimethyl(trifluoromethyl)tin (754-25-6) + dimethylcadmium (506-82-1) + dimethylbis(trifluoromethyl)tin (65059-36-1)

Conditions	Yield
In dichloromethane byproducts: Sn(CH3)4, C2F4, CH3I; excess of Cd compd. quickly added to SnI4 in CH2Cl2, sepd. after 15 min; solvent removed;	A 23% B n/a C 10%

methyl magnesium iodide (917-64-6) → dimethylcadmium (506-82-1)

Conditions	Yield
With cadmium(II) chloride
With diethyl ether; cadmium(II) bromide
With diethyl ether; cadmium(II) iodide at 25℃;

methylmagnesium bromide (75-16-1) → dimethylcadmium (506-82-1)

Conditions	Yield
With diethyl ether; cadmium(II) bromide
With diethyl ether; cadmium(II) chloride

methyl magnesium (1+); bromide + CdBr2 → dimethylcadmium (506-82-1)

diethyl ether (60-29-7) + methyl magnesium (1+); bromide + CdCl2 → dimethylcadmium (506-82-1)

methyl iodide (74-88-4) → dimethylcadmium (506-82-1) + CdI2 and C2H6

Conditions	Yield
With cadmium at 110℃;

methyllithium (917-54-4) + cadmium(II) chloride (10108-64-2) → dimethylcadmium (506-82-1)

Conditions	Yield
In tetrahydrofuran; diethyl ether room temp.; distn.;	>90

dimethylmagnesium (2999-74-8) + cadmium(II) chloride (10108-64-2) → dimethylcadmium (506-82-1)

Conditions	Yield
In diethyl ether under N2 atm. Et2O soln. Grignard reagent was added dropwise for 2 h to stirred suspn. CdCl2 in Et2O in protected from light vessel and stirred for 12 h; Et2O was removed at reduced pressure;

(CH3)2Cd(C10H8N2) → dimethylcadmium (506-82-1)

Conditions	Yield
byproducts: diethyl ether; heated; vacuum distilled, held at 2°C, distilled into two traps (-30°C, -196°C);

CH3CdS2CN(C2H5)2 → dimethylcadmium (506-82-1)

Conditions	Yield
decompn.;

cadmium(II) acetate (543-90-8) → dimethylcadmium (506-82-1)

Conditions	Yield
at 28.69℃; Temperature;

[tris(2-mercapto-1-t-butylimidazolyl)hydroborato]CdMe + dimethyl zinc(II) (544-97-8) → methyl(tris(2-mercapto-1-tert-butylimidazolyl)hydroborate)zinc + dimethylcadmium (506-82-1)

Conditions	Yield
In (2)H8-toluene at 26.84℃; Equilibrium constant; Solvent; Inert atmosphere; Schlenk technique; Glovebox;

dimethylcadmium (506-82-1) + trifluoromethyltribromostannane (65094-19-1) → trimethyl(trifluoromethyl)tin (754-25-6)

Conditions	Yield
tenfold excess of Cd(CH3)2, 20°C (15 min);	100%
tenfold excess of Cd(CH3)2, 20°C (15 min);	100%
small excess of Cd(CH3)2, 20°C (15 min);	92%
small excess of Cd(CH3)2, 20°C (15 min);	92%

dimethylcadmium (506-82-1) + pentafluroethyltriiodogermane (66348-24-1) → C2F5Ge(CH3)3 (66348-25-2)

Conditions	Yield
twofold excess of Cd(CH3)2; 20°C, 24 h;	100%

1,3,5-Triisopropyl-1,3,5-triazacyclohexane (10556-98-6) + dimethylcadmium (506-82-1) → dimethylcadmium-bis(hexahydro-1,3,5-triisopropyl-1,3,5-triazine)

Conditions	Yield
In neat (no solvent) (N2 free of O2) amine slowly added to dimethylcadmium at -196°C, warmed to room temp.; distd. (140°C, E-2 Torr); elem. anal.;	99.2%

Mesitol (527-60-6) + dimethylcadmium (506-82-1) → cadmium 2,4,6-trimethylphenolate

Conditions	Yield
In diethyl ether (N2); stirring (overnight), reflux (1 h); solvent removal (vac.), washing (Et2O), drying; elem. anal.;	99%

1,3,5-trimethyl-1,3,5-triazacyclohexane (108-74-7) + dimethylcadmium (506-82-1) → dimethylcadmium-bis(hexahydro-1,3,5-trimethyl-1,3,5-triazine)

Conditions	Yield
In neat (no solvent) (N2 free of O2) amine slowly added to dimethylcadmium at -196°C, warmed to room temp.; sublimed (120°C, E-2 Torr); elem. anal.;	98.9%

1,3,5-triethyl-1,3,5-triazacyclohexane (7779-27-3) + dimethylcadmium (506-82-1) → dimethylcadmium-bis(hexahydro-1,3,5-triethyl-1,3,5-triazine)

Conditions	Yield
In neat (no solvent) (N2 free of O2) amine slowly added to dimethylcadmium at -196°C, warmed to room temp.; distd. (140°C, E-2 Torr); elem. anal.;	98.4%

diethylboric acid (4426-31-7) + dimethylcadmium (506-82-1) → [(μ(3)-Et2BO)CdMe]4 (251948-39-7)

Conditions	Yield
In toluene byproducts: EtBMe2, CH4; Ar-atmosphere; dropwise addn. of 1 equiv. Et2BOH to CdMe2 (-20°C,stirring), stirring at room temp. for 30 min; removal of volatiles (reduced pressure);	98%

dimethylcadmium (506-82-1) + stearic acid (57-11-4) → cadmium(II) stearate (2223-93-0)

Conditions	Yield
In benzene	96.3%

dimethylcadmium (506-82-1) + p-Toluic acid (99-94-5) → Cd[O2C(C6H4-4-Me)]2

Conditions	Yield
In toluene at 20℃; for 0.5h;	96%

N-amino-N'-methylpiperazine (6928-85-4) + dimethylcadmium (506-82-1) → Cd(2+)*2CH3(1-)*NH2N(CH2)4NCH3=Cd(CH3)2(NH2N(CH2)4NCH3)

Conditions	Yield
In hexane hexane soln. of Me2Cd added to hexane; then 1-amino-4-methylpiperazine added; mixt. stirred; elem. anal.;	94%

dimethylcadmium (506-82-1) + perfluormethylgermanium iodide (754-36-9) → Dimethyl-bis-trifluoromethyl-germane (66348-20-7)

Conditions	Yield
twofold excess of Cd(CH3)2; 20°C, 24 h;	92%

C12H25N2PS2 + dimethylcadmium (506-82-1) → Cd{iPr2P(S)NC(S)NC5H10-κ2-S,S}2

Conditions	Yield
In toluene Schlenk technique; Inert atmosphere;	92%

bis(trimethylsilyl)selenide (4099-46-1) + dimethylcadmium (506-82-1) → cadmium(II) selenide

Conditions	Yield
In dichloromethane byproducts: Si(CH3)4; stirred at 25°C for 4 h; filtered, powder annealed in vacuo (400°C, 4 h); X-ray powder diffraction;	91%
In toluene byproducts: Si(CH3)4; stirred at 25°C, reaction is fairly slow, taked days to go compled; proton NMR;
In further solvent(s) under argon, soln. of Me2Cd in (n-C8H17)3P and soln. of ((CH3)3Si)2Se in (n-C8H17)3P are combined and added under vigorous stirring to (n-C8H17)3PO at 300°C, heat removed (180°C) then gradually raised to 230-260°C; cooled to 60°C, methanol added, centrifugated, dispersed (1-butanol), centrifugated, precipitate discarded, methanol added to the supernatant, flocculate rinsed (methanol), dried (vacuum);

dimethylcadmium (506-82-1) + bis(trifluoromethyl)dibromostannane (65094-20-4) → trimethyl(trifluoromethyl)tin (754-25-6) + dimethylbis(trifluoromethyl)tin (65059-36-1)

Conditions	Yield
educts separately condensed into a reactor held at -196°C, then allowed to react for 35 min at room temp.; volatile products were removed and analyzed, identification by NMR;	A n/a B 91%

dimethylcadmium (506-82-1) + tris(trifluoromethyl)germyl iodide (66348-18-3) → Methyl-tris-trifluoromethyl-germane (66348-19-4)

Conditions	Yield
twofold excess of Cd(CH3)2; 20°C, 24 h;	90%

vanadocene + dimethylcadmium (506-82-1) → dimethylvanadocene (62363-03-5) + cadmium (7440-43-9)

Conditions	Yield
In neat (no solvent) V-compd. added to Cd-compd. at room temp., immediate reaction; extd. (pentane);	A 90% B n/a

(74)GeCl4 + dimethylcadmium (506-82-1) → tetramethylgermane (240817-41-8)

Conditions	Yield
In neat (no solvent) byproducts: CdCl2; components (5% Cd-compd. excess) vac. distn. into Pyrex tube with Teflonstopcock, mixt. allowing to warm to room temp.; Ge-compd. pumping off the solid byproduct; FTIR spectroscopy;	90%

C12H25N2OPS + dimethylcadmium (506-82-1) → Cd{iPr2P(S)NC(O)NC5H10-κ2-S,O}2

Conditions	Yield
In toluene Schlenk technique; Inert atmosphere;	90%

dimethylcadmium (506-82-1) + [1,4]naphthoquinone (130-15-4) → 4-hydroxy-4-methyl-1(4H)-naphthalenone (42860-82-2)

Conditions	Yield
In tetrahydrofuran 1.) -10 deg C, 1 h, 2.) -10 deg C -> room temperature;	89%

dimethylcadmium (506-82-1) + diethylamine (109-89-7) → CH3CdS2CN(C2H5)2

Conditions	Yield
With CS2 In toluene byproducts: CH4; (N2); dimethylcadmium and diethylamine stirred and heated at 70°C for 12 h; cooled; added CS2; warmed to 40°C for 5 h; filtered; evapd.; recrystd. from benzene; elem. anal.;	89%

N-(1-(5,7-di-tert-butyl-2-methyl-2,3-dihydrobenzo[d]oxazol-2-yl)ethylidene)-2,6-diisopropylaniline + dimethylcadmium (506-82-1) → methyl cadmium (2,4-di-tert-butyl-6-(3-(2,6-diisopropylphenylimino)butan-2-ylidene)aminophenolate)

Conditions	Yield
In diethyl ether	89%

C12H25N2OPS + dimethylcadmium (506-82-1) → Cd{iPr2P(O)NC(S)NC5H10-κ2-O,S}2

Conditions	Yield
In toluene Schlenk technique; Inert atmosphere;	89%

dimethylcadmium (506-82-1) + bis(dimethyl-i-propylsilyl)telluride (123676-74-4) → cadmium telluride

Conditions	Yield
In dichloromethane byproducts: Si(i-Pr)Me3; stirred at 25°C for 15 min; filtered, annealed (400°C, 2 h);	88%

1,3-bis(dimethylamino)-2-(dimethylaminomethyl)-propan-2-ol (862277-33-6) + dimethyl zinc(II) (544-97-8) + dimethylcadmium (506-82-1) → [(MeCd)(MeZn)(1,3-bis(dimethylamino)-2-(dimethylaminomethyl)propan-2-olate)2]

Conditions	Yield
In hexane (inert atm.); addn. of aminoalcohol deriv. to hexane soln. of cadmium compd. and zinc compd. at -78°C, stirring for 1 h, warming to room temp.; heating to 60°C, cooling to room temp., elem. anal.;	87%

dimethylcadmium (506-82-1) + 8-Methyl-1,2,3,4-tetrahydro-naphthalene-1-carbonyl chloride (81603-45-4) → 8-methyl-1,2,3,4-tetrahydro-1-naphthyl methyl ketone (81603-31-8)

Conditions	Yield
In benzene for 1h; Heating;	85%

dimethylcadmium (506-82-1) + 2-((2,6-diisopropylphenyl)amino)-4-((2,6-diisopropylphenyl)imino)-2-pentene (289618-59-3) → (CH3)2C2NCHN((CH(CH3)2)2C6H3)2CdCH3 (1234205-23-2)

Conditions	Yield
In benzene (under N2, Schlenk); Cd(CH3)2 added to soln. of ligand in benzene, refluxed for 16 h, Cd(CH3)2 added, refluxed for 16 h; volatiles removed in vacuo, extd. into benzene, lyophilized;	85%

1,4,8,11-tetramethyl-1,4,8,11-tetra-azacyclotetradecane (41203-22-9) + dimethylmagnesium (2999-74-8) + dimethylcadmium (506-82-1) + benzene (71-43-2) → [MgMe(1,4,7,11-tetramethyl-1,4,7,11-tetraazacyclotetradecane)][CdMe3] * benzene

Conditions	Yield
In tetrahydrofuran	83%

Upstream product

• 544-97-8 dimethyl zinc(II) 
• 543-90-8 cadmium(II) acetate 
• 2999-74-8 dimethylmagnesium 
• 10108-64-2 cadmium(II) chloride 
• 917-54-4 methyllithium 
• 74-88-4 methyl iodide 
• 60-29-7 diethyl ether 
• 75-16-1 methylmagnesium bromide 
• 917-64-6 methyl magnesium iodide 

Downstream Products

• 18761-46-1 1-(5-ethyl-thiophen-2-yl)-ethanone 
• 13679-72-6 2-acetyl-3-methylthiophene 
• 1689-09-4 3,3-Dimethyl-3H-isobenzofuran-1-one 
• 577-56-0 2-acetyl-benzoic acid 
• 430-51-3 1-fluoro-2-propanone 
• 104550-70-1 3-butyl-3,4-pentadien-2-one 
• 2142-64-5 1-(2-ethylphenyl)ethanone 
• 776-99-8 3,4-dimethoxyphenylacetone 
• 629-66-3 nonadecan-2-one 
• 38480-94-3 2,3-dimethoxyacetophenone 
• 3637-01-2 3,4-dimethylacetophenone 
• 3664-64-0 rac-4,8-dimethyl-7-nonen-2-one 
• 337-16-6 2-hydroxy-2-methyl-3,3,3-trifluoropropionic acid methyl ester 
• 593-80-6 dimethyltellurium 

Relevant articles and documents

Mixed alkyl dialkylthiocarbamates of zinc and cadmium: Potential precursors for II/VI materials. X-ray crystal structure of [MeZnS2CNEt2]2

Compounds with the formula RMS2CNR′2 (R or R′ = Me or Et, M = Zn; R = Me, R′ = Et, M = Cd) have been synthesized and characterized. An X-ray crystal structure for MeZnS2CNEt2 has been determined and shows the complex to be dimeric. The compound crystallizes in space group P21/c, a = 6.776 (1) ?, b = 10.341 (4) ?, and c = 10.341 (4) ?, α = 90°, β = 97.3 (3)°, and γ = 90°. The zinc complexes may be useful precursors for the deposition of ZnS.

Exchange of alkyl and tris(2-mercapto-1-t-butylimidazolyl)hydroborato ligands between zinc, cadmium and mercury

Abstract The tris(2-mercaptoimidazolyl)hydroborato ligand, [TmBut], has been used to investigate the exchange of alkyl and sulfur donor ligands between the Group 12 metals, Zn, Cd and Hg. For example, [TmBut]2Zn reacts with Me2Zn to yield [TmBut]ZnMe, while [TmBut]CdMe is obtained readily upon reaction of [TmBut]2Cd with Me2Cd. Ligand exchange is also observed between different metal centers. For example, [TmBut]CdMe reacts with Me2Zn to afford [TmBut]ZnMe and Me2Cd. Likewise, [TmBut]HgMe reacts with Me2Zn to afford [TmBut]ZnMe and Me2Hg. However, whereas the [TmBut] ligand transfers from mercury to zinc in the methyl system, [TmBut]HgMe/Me2Zn, transfer of the [TmBut] ligand from zinc to mercury is observed upon treatment of [TmBut]2Zn with HgI2 to afford [TmBut]HgI and [TmBut]ZnI. These observations demonstrate that the phenomenological preference for the [TmBut] ligand to bind one metal rather than another is strongly influenced by the nature of the co-ligands.

Reactions of diorganocadmium compounds with other dialkylmetal compounds and macrocycles: Synthesis of organocadmate anions

Combining R2Cd (R an alkyl or Ph group), the corresponding R2Mg compound, and 1,4,8,11-tetramethyl-1,4,8,11-tetraazatetradecane, 2,1,1-cryptand, or 2,2,1-cryptand in solution quantitatively produces R3Cd-1 and R