544-97-8

Basic information

• Product Name: DIMETHYLZINC
• Synonyms: Dimethylzinc,elec.gr.(99.999%-Zn)PURATREM;Dimethylzinc,min.95%;Dimethylzinc,min.95%(10wt%inhexane)(Sure/Sealbottle);DIMETHYLZINC (10 WT% IN HEXANE);Dimethylzinc, 95+%;Dimethylzinc1.2M solution in tolueneAcroSeal§3;Dimethylzinc, min. 99% (10 wt% in hexane) (Sure/Sealbottle);DIMETHYL ZINC, PURE
• CAS NO: 544-97-8
• Molecular Formula: C₂H₆Zn
• Molecular Weight: 95.46
• EINECS: 208-884-1
• Product Categories: Dialkylzincs;Organometallic Reagents;Reike and Organozinc Reagents;metal alkyl;Chemical Synthesis;Organometallic Reagents;Rieke and Organozinc Reagents;ALD Precursors
• Mol File: 544-97-8.mol
• Article Data: 21

Chemical Properties

• Melting Point: -42°C
• Boiling Point: 44-46 °C
• Flash Point: 30 °F
• Appearance: colorless/liquid
• Density: 0.92 g/mL at 20 °C
• Storage Temp.: 0-6°C
• Sensitive: Air & Moisture Sensitive
• Merck: 14,3263
• BRN: 3587195
• CAS DataBase Reference: DIMETHYLZINC(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYLZINC(544-97-8)
• EPA Substance Registry System: DIMETHYLZINC(544-97-8)

Safety Data

• Hazard Codes: F,C,N,Xn
• Statements: 11-14-34-50/53-65-67-63-51/53-48/20-17-14/15-36/38
• Safety Statements: 26-45-61-62-60-43-36/37/39-33-29-16-46-43A-36/37
• RIDADR: UN 3399 4.3/PG 2
• WGK Germany: 2
• F: 10-23
• TSCA: Yes
• HazardClass: 4.2
• PackingGroup: I
• Hazardous Substances Data: 544-97-8(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

Uses

Different sources of media describe the Uses of 544-97-8 differently. You can refer to the following data:
1. Dimethylzinc is pharmaceutical compound comprising Hemiasterlin derivatives and its antibody conjugate for treatment of cancer.
2. Dimethylzinc solution can be used as:A catalyst with nickel for the stereoselective C?2 alkenylation and dialkenylation of pyridine derivatives by alkynes to give monoalkenylation products.A reagent with aldehydes and 2-methoxyaniline for the synthesis of enantioselective alkyl and aralkyl secondary amines via one-pot three-component coupling reaction in the presence of zirconium tetraisopropoxide.A methylating reagent for methylation of fluoroalkylated pyruvates in the presence of copper/chiral diphosphine catalyst.
3. Activator for radical trifluoromethylation of silyl enol ethers leading to α-trifluoromethyl ketones.1

General Description

Mobile liquid, with peculiar garlic odor.

Air & Water Reactions

Highly flammable. Ignites in air and burns with a blue flame giving off a peculiar garlicky odor. Explodes in oxygen or ozone. Reacts violently with water to generate methane [Merck, 11th ed., 1989; Brauer(1965)]. Very slow oxidation with traces of air to give methylzinc methylate.

Reactivity Profile

DIMETHYLZINC is very reactive, acts as a strong reducing agent. Combines with acids, with alcohols (methanol, ethanol), and 2-2-dichloropropane as well as with water with explosive violence. When heated to decomposition emits toxic fumes of zinc oxide [Bretherick, 5th ed., 1995, p. 354]. Oxidants may yield peroxide formation, which is explosive.

Health Hazard

Inhalation of mist or vapor causes immediate irritation of upper respiratory tract. Excessive or prolonged inhalation of fumes from ignition or decomposition may cause ``metal fume fever'' (sore throat, headache, fever, chills, nausea, vomiting, muscular aches, perspiration, constricting sensation in lungs, weakness, sometimes prostration). Symptoms usually last 12-24 hrs. Eyes are immediately and severely irritated by liquid, vapor, or dilute solutions. If not removed by thorough flushing with water, chemical may permanently damage cornea. Skin will undergo thermal and acid burns when chemical reacts with moisture in skin. Unless washed quickly, skin may be scarred. Treat dilute solutions with same precautions as concentrated liquid. Ingestion, while unlikely, would cause immediate burns at site of contact. Nausea, vomiting, cramps, and diarrhea may follow. Tissues may ulcerate if not treated.

InChI:InChI=1/2CH3.Zn/h2*1H3;/rC2H6Zn/c1-3-2/h1-2H3

Synthetic route

zinc(II) fluoride + trimethylaluminum (75-24-1) → dimethyl zinc(II) (544-97-8)

Conditions	Yield
at 75℃; for 6.5h; Inert atmosphere;	95%

trimethylaluminum (75-24-1) + zinc dibromide → dimethyl zinc(II) (544-97-8)

Conditions	Yield
at 90℃; for 7h; Inert atmosphere;	94%

trimethylaluminum (75-24-1) + zinc(II) chloride (7646-85-7) → dimethyl zinc(II) (544-97-8)

Conditions	Yield
at 60℃; for 6h; Inert atmosphere;	92%

zinc (7440-66-6) + methyl iodide (74-88-4) → dimethyl zinc(II) (544-97-8)

Conditions	Yield
With copper(l) iodide In neat (no solvent) CuI, Zn were placed in reactor, evacuated for 10 min, filled with Ar, Al-compound and ligand were added, heated to 42°C for 12 h, cooled to room temp.; vac. distilled;	90%

methyl magnesium iodide (917-64-6) + zinc(II) chloride (7646-85-7) → dimethyl zinc(II) (544-97-8)

Conditions	Yield
In dibutyl ether soln. MeMgI in n-Bu2O was slowly added to ZnCl2 under vigorous stirring,suspn. was heated at 60°C for 60 h; ZnMe2 was collected by distillation in temp. range 130-160°C;	75%

[Zn(Pd(N(FC6H3P(C3H7)2)2))2] (1000391-90-1) + methyl iodide (74-88-4) → Pd(CH3)(N(C6H3(F)P(CH(CH3)2)2)2) (798541-83-0) + dimethyl zinc(II) (544-97-8)

Conditions	Yield
In benzene-d6 Irradiation (UV/VIS); at room temp. up to 5 d; NMR;	A n/a B 60%

[tris(trimethylsilyl)germyl]zinc chloride mono-tetrahydrofuran solvate + methyllithium (917-54-4) → (Me3Si)3GeZnMe + bis[tris(trimethylsilyl)germyl]zinc + dimethyl zinc(II) (544-97-8)

Conditions	Yield
In tetrahydrofuran under Ar; THF soln. of MeLi and germylzinc stirred at room temp. for 1.5h;	A 0% B 50% C 50%
In diethyl ether germylzinc compd. reacted with 1 mol Li compd.; symmetrical compds. yielded in quantitative reaction in ratio of 1:1 (detmd. by (1)H NMR);	A 0% B n/a C n/a

methylmagnesium bromide (75-16-1) → dimethyl zinc(II) (544-97-8)

Conditions	Yield
With diethyl ether; zinc(II) chloride

diethylzinc (557-20-0) + methylmercury(II) iodide (143-36-2) → dimethyl zinc(II) (544-97-8) + diethylmercury (627-44-1)

dimethylmercury (593-74-8) → dimethyl zinc(II) (544-97-8)

Conditions	Yield
With zinc at 120℃;

Tetramethylblei-(IV) (75-74-1) → dimethyl zinc(II) (544-97-8)

Conditions	Yield
Durch thermische Zersetzung unter vermindertem Druck und Einw. des entstandenen Methyls auf metallisches Zink;

methylzinc iodide (18815-73-1) → dimethyl zinc(II) (544-97-8)

Conditions	Yield
at 25℃;

methyl iodide (74-88-4) → dimethyl zinc(II) (544-97-8)

Conditions	Yield
With sodium amalgam; acetic acid ester; zinc man verwendet einen kupfernen Kessel und destilliert aus dem Oelbad bei moeglichst niedriger Temperatur;
With zinc at 150 - 160℃;
With diethyl ether; zinc at 100℃; Destillation des Reaktionsproduktes;

methyl radical (2229-07-4) + zinc → dimethyl zinc(II) (544-97-8)

4ethyl iodide → dimethyl zinc(II) (544-97-8)

Conditions	Yield
With zinc at 100℃; Destillation des Reaktionsproduktes;

dimethylmercury (593-74-8) + zinc → dimethyl zinc(II) (544-97-8) + mercury

Conditions	Yield
at 120℃;

diethylzinc (557-20-0) + methylmercury(II) iodide (143-36-2) → dimethyl zinc(II) (544-97-8) + diethylmercury (627-44-1) + zinc iodide

methyl iodide (74-88-4) → dimethyl zinc(II) (544-97-8) + ZnI2

Conditions	Yield
With zinc Destillation des entstehenden intermediaeren Methylzinkjodid;

zinc diacetate (557-34-6) + trimethylaluminum (75-24-1) → dimethyl zinc(II) (544-97-8)

Conditions	Yield
In dodecane excess of Me3Al in dodecane adding to suspn. of anhyd. Zn acetate in dodecane at room temp.; mixt. distg. through a 40 cm vigreux column and product collecting in toluene; identified by b. p.;

zinc (7440-66-6) → dimethyl zinc(II) (544-97-8)

Conditions	Yield
With copper; methyl iodide In neat (no solvent) sealed tube (vac.), Zn/Cu powder contg. 91 % Zn, 373 K (20 h); cooling to 77 K, opening, fractional distn. (vac.);
With hydrogen; copper(II) oxide; methyl iodide In dichloromethane heating Zn and CuO under H2 (color change from black to gray), purging with N2, cooling to room temp., slow addn. of CH3I via the dropping funnel, heating at 65-70°C for abbout 18 h, allowing to come to room temp., cooling to -78°C; whole operation in a hood; Liebig cooler with flasks (CH2Cl2), flasks are cooled (dry ice/acetone bath), distn. at atmospheric pressure, heating of flask (oil bath, 200°C);	70-75

methyllithium (917-54-4) + zinc(II) chloride (7646-85-7) → dimethyl zinc(II) (544-97-8)

Conditions	Yield
In tetrahydrofuran; diethyl ether (Ar); stirring (0°C, 30 min.);
In tetrahydrofuran-d8 under Ar; to mixt. of ZnCl2 and MeLi addded THF-D8 in NMR tube at low temp., allowed to warm to room temp., stirred for 5 min, not isolated;
In diethyl ether (inert atmosphere); not isolated;
In tetrahydrofuran; diethyl ether at 0℃; for 0.5h; Schlenk technique;

zinc copper → dimethyl zinc(II) (544-97-8)

Conditions	Yield
With methyl iodide In neat (no solvent) reaction of MeI with CuZn (excess of Zn);

dimethylcadmium (506-82-1) + ethylzinc(II) iodide (32955-11-6) → dimethyl zinc(II) (544-97-8) + methylethylcadmium (55204-73-4)

Conditions	Yield
In gaseous matrix components vaporization into He, mixt. diln. further with He or H2, equilibration within 20 s in IR cell; IR spectroscopic monitoring;

ammonia (7664-41-7) + methylzinc tetrahydroborate → hexa-amminezinc tetrahydroborate + dimethyl zinc(II) (544-97-8)

Conditions	Yield
In neat (no solvent) (exclusion of moisture); co-condensation of MeZnBH4 and NH3, maintainingthe mixture at -78°C for ca. 24 h, removal of excess NH3 at -78. degree.C, slow warming to room temp. under continuous pumping; elem. anal.;

zinc (7440-66-6) + 1,2-dibromomethane (74-95-3) → bis(bromomethyl)zinc (92601-82-6) + dimethyl zinc(II) (544-97-8) + bromomethylzinc bromide (4109-95-9)

Conditions	Yield
In tetrahydrofuran; tetrahydrofuran-d8 byproducts: ethylene, methyl bromide; 35-40°C, molar ratio of Zn:CH2Br2 is 1:1 to 1:4;

methylethylcadmium (55204-73-4) + ethylzinc(II) iodide (32955-11-6) → dimethyl zinc(II) (544-97-8) + diethylcadmium (592-02-9)

Conditions	Yield
In gaseous matrix components vaporization into He, mixt. diln. further with He or H2, equilibration within 20 s in IR cell; IR spectroscopic monitoring;

methylzinc tetrahydroborate → zinc(II) tetrahydroborate + dimethyl zinc(II) (544-97-8)

Conditions	Yield
In neat (no solvent) (exclusion of moisture); 190 K, continuous pumping;

methylmagnesium bromide (75-16-1) + zinc(II) chloride (7646-85-7) → dimethyl zinc(II) (544-97-8)

Conditions	Yield
In tetrahydrofuran; diethyl ether at 20℃; for 0.75h;
In diethyl ether for 2h; Reflux; Inert atmosphere;
In diethyl ether

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

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

1-Bromonaphthalene (90-11-9) + dimethyl zinc(II) (544-97-8) → 1-Methylnaphthalene (90-12-0)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane for 2h; Heating;	100%
Stage #1: 1-Bromonaphthalene; dimethyl zinc(II) With n-butyllithium In tetrahydrofuran; diethyl ether; hexane at 0℃; for 0.5h; Substitution; Stage #2: With oxovanadium(V) ethoxydichloride In tetrahydrofuran; diethyl ether; hexane at 20℃; for 3h; Oxidation; Alkylation; Further stages.;	73%

carbon dioxide (124-38-9) + dimethyl zinc(II) (544-97-8) + phenylacetylene (536-74-3) → (E)-3-phenyl-2-butenoic acid (704-80-3)

Conditions	Yield
Stage #1: carbon dioxide; phenylacetylene With bis(1,5-cyclooctadiene)nickel (0); 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0℃; for 1h; Stage #2: dimethyl zinc(II) In tetrahydrofuran; hexane at 0℃; for 2h; Further stages.;	100%

4-Bromobenzoic acid (586-76-5) + dimethyl zinc(II) (544-97-8) → p-Toluic acid (99-94-5)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane for 2h; Heating;	100%

2-bromophenyl methyl ketone (2142-69-0) + dimethyl zinc(II) (544-97-8) → 2-Methylacetophenone (577-16-2, 122382-54-1)

Conditions	Yield
(1,2-bis(diphenylphosphino)ethane)palladium(II) chloride In 1,4-dioxane for 1.5h; Heating;	100%

4-bromophenethanol (4654-39-1) + dimethyl zinc(II) (544-97-8) → 2-(p-methylphenyl)ethanol (699-02-5)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane for 1h; Heating;	100%

4-bromo-2-nitrobenzoic acid (99277-71-1) + dimethyl zinc(II) (544-97-8) → 4-methyl-2-nitrobenzoic acid (27329-27-7)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane for 2h; Heating;	100%

dimethyl zinc(II) (544-97-8) + para-bromoacetophenone (99-90-1) → para-methylacetophenone (122-00-9)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane for 1h; Heating;	100%

diazomethane (186581-53-3, 908094-01-9) + carbon dioxide (124-38-9) + dimethyl zinc(II) (544-97-8) + 1-methoxy-4-(4-phenylbut-1-yn-1-yl)benzene → (E)-methyl 3-(4-methoxyphenyl)-2-phenethyl-2-butenoate

Conditions	Yield
Stage #1: carbon dioxide; dimethyl zinc(II); 1-methoxy-4-(4-phenylbut-1-yn-1-yl)benzene With bis(1,5-cyclooctadiene)nickel (0); 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; hexane at 20℃; Stage #2: diazomethane In diethyl ether at 0℃;	100%

(3Z,5R,6R,7E,9S)-1-trimethylsilyl-3-bromo-5,7,9-trimethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-3,7-undecadien-1-yne (770711-59-6) + dimethyl zinc(II) (544-97-8) → (3E,5R,6R,7E,9S)-1-trimethylsilyl-3,5,7,9-tetramethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-3,7-undecadien-1-yne (770711-60-9)

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran; toluene at 23℃; for 1h;	100%

C18H17F4NO3S + dimethyl zinc(II) (544-97-8) → (-)-5-(4-fluorophenyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine

Conditions	Yield
Stage #1: C18H17F4NO3S; dimethyl zinc(II); (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; toluene for 2h; Heating / reflux; Stage #2: With methanol; water In 1,4-dioxane; ethyl acetate; toluene	100%

((CH3)5C5)Co((C2H5)2C2B3H3)Ta(Cl)2(C5H5) + dimethyl zinc(II) (544-97-8) → ((CH3)5C5)Co((C2H5)2C2B3H3)Ta(CH3)(Cl)(C5H5)

Conditions	Yield
In tetrahydrofuran; diethyl ether stirring (room temp., 0.5 h); evapn., chromy. (petroleum ether / CH2Cl2 = 3 : 1); elem. anal.;	100%

(HOC6H2(C(CH3)3)CH2)2(C6H2(C(CH3)3)(CCC6H5)CH2)2 (868840-71-5) + dimethyl zinc(II) (544-97-8) → (CH3)2Zn2((OC6H2(C(CH3)3)CH2)2(C6H2(C(CH3)3)(CCC6H5)CH2)2) (947622-65-3)

Conditions	Yield
In toluene under N2; soln. of ZnMe2 in toluene added to soln. of ligand in toluene;stirred at room temp. for 8 h; volatiles evapd.;	100%

(HOC6H2(C(CH3)3)CH2)2(C6H2(C(CH3)3)(CCC6H4CH3)CH2)2 (947622-63-1) + dimethyl zinc(II) (544-97-8) → (CH3)2Zn2((OC6H2(C(CH3)3)CH2)2(C6H2(C(CH3)3)(CCC6H4CH3)CH2)2) (947622-67-5)

Conditions	Yield
In toluene under N2; soln. of ZnMe2 in toluene added to soln. of ligand in toluene;stirred at room temp. for 8 h; volatiles evapd.; elem. anal.;	100%

(HOC6H2(C(CH3)3)CH2)2(C6H2(C(CH3)3)(CCC6H4OCH3)CH2)2 (947622-62-0) + dimethyl zinc(II) (544-97-8) → (CH3)2Zn2((OC6H2(C(CH3)3)CH2)2(C6H2(C(CH3)3)(CCC6H4OCH3)CH2)2) (947622-66-4)

Conditions	Yield
In toluene under N2; soln. of ZnMe2 in toluene added to soln. of ligand in toluene;stirred at room temp. for 8 h; volatiles evapd.; elem. anal.;	100%

5,11,17,23-tetra(tert-butyl)-25,27-dihydroxy-26,28-bis[p-(trifluoromethyl)phenylethynyl]calix[4]arene (943231-28-5) + dimethyl zinc(II) (544-97-8) → (CH3)2Zn2((OC6H2(C(CH3)3)CH2)2(C6H2(C(CH3)3)(CCC6H4CF3)CH2)2) (947622-68-6)

Conditions	Yield
In toluene under N2; soln. of ZnMe2 in toluene added to soln. of ligand in toluene;stirred at room temp. for 8 h; volatiles evapd.; elem. anal.;	100%

(HOC6H2(C(CH3)3)CH2)2(C6H2(C(CH3)3)(CCC6H4CF3)CH2)C6H2(C(CH3)3)(CCC6H4OCH3)CH2 (947622-79-9) + dimethyl zinc(II) (544-97-8) → (CH3)2Zn2((OC6H2(C(CH3)3)CH2)2(C6H2(C(CH3)3)(CCC6H4CF3)CH2)C6H2(C(CH3)3)(CCC6H4OCH3)CH2) (947622-80-2)

Conditions	Yield
In toluene under N2; soln. of ZnMe2 in toluene added to soln. of ligand in toluene;stirred at room temp. for 8 h; volatiles evapd.; elem. anal.;	100%

(HOC6H2(C(CH3)3)CH2)2(C6H2(C(CH3)3)(CCC6H3(CF3)2)CH2)2 (947622-64-2) + dimethyl zinc(II) (544-97-8) → (CH3)2Zn2((OC6H2(C(CH3)3)CH2)2(C6H2(C(CH3)3)(CCC6H3(CF3)2)CH2)2) (947622-69-7)

Conditions	Yield
In toluene under N2; soln. of ZnMe2 in toluene added to soln. of ligand in toluene;stirred at room temp. for 8 h; volatiles evapd.;	100%

(3aR,4E,7aS)-4-(bromomethylene)-3a,4,5,6,7,7a-hexahydro-7a-methyl-3H-indene-1-carbaldehyde (939994-88-4) + dimethyl zinc(II) (544-97-8) → (S)-1-{(3aS,7E,7aR)-7-(bromomethylene)-3a,4,5,6,7,7a-hexahydro-3a-methyl-1H-indene-3-yl}ethanol (939994-50-0)

Conditions	Yield
With titanium(IV) isopropylate; N,N’-(1R,2R)-cyclohexane-1,2-diylbis(1,1,1-trifluoromethanesulfonamide) In tert-butyl methyl ether at 20℃; for 1h; Product distribution / selectivity;	100%

dimethyl(phenyl)silyl lithium (3839-31-4) + 1-Bromo-2-iodobenzene (583-55-1) + dimethyl zinc(II) (544-97-8) → Dimethyldiphenylsilane (778-24-5)

Conditions	Yield
Stage #1: dimethyl(phenyl)silyl lithium; dimethyl zinc(II) In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: 1-Bromo-2-iodobenzene In tetrahydrofuran; hexane at 20℃; for 16h; Further stages.;	100%

C52H70O8SSi (1160221-66-8) + dimethyl zinc(II) (544-97-8) → C51H68O8Si (1160221-67-9)

Conditions	Yield
With zinc trifluoromethanesulfonate In hexane; dichloromethane at 0 - 20℃; for 1h;	100%
With zinc trifluoromethanesulfonate In hexane; dichloromethane at 0 - 20℃; for 1h;	100%
With zinc trifluoromethanesulfonate In hexane; dichloromethane at 0 - 20℃;	100%

C31H59IO2Si2 + dimethyl zinc(II) (544-97-8) → C32H62O2Si2

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃;	100%

5-bromo-N-methylimidazole (1003-21-0) + dimethyl zinc(II) (544-97-8) → 1,2-dimethylimidazole (10447-93-5)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; diisobutylaluminium hydride In 1,4-dioxane at 100℃; for 2.5h;	100%

methyl 6-(2,6-difluoro-3-(trifluoromethylsulfonyloxy)-phenyl)picolinate (1210419-46-7) + dimethyl zinc(II) (544-97-8) → methyl 6-(2,6-difluoro-3-methylphenyl)picolinate (1210419-50-3)

Conditions	Yield
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In toluene at 80℃; for 2h;	100%

C32H51F3O6SSi2 + dimethyl zinc(II) (544-97-8) → C32H54O3Si2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In hexane at 0 - 20℃; for 12h; Inert atmosphere;	100%
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; hexane at 0 - 20℃; for 12h;	69.5 mg

Re(κ1(P)-6-(diphenylphosphino)-2,2'-bipyridine)(CO)5][OTf] (1291092-82-4) + dimethyl zinc(II) (544-97-8) → [Re(κ1(P)-6-(diphenylphosphino)-2,2'-bipyridine*ZnMe)(μ2-COMe)(CO)4][OTf] (1291092-89-1)

Conditions	Yield
In dichloromethane-d2 Zn compd. added to a soln. of Re complex, shaken; evapd. (vac.), triturated with pentane; obtained as an oil; elem. anal.;	100%

4'-bromo-2,2,2-trifluoroacetophenone (16184-89-7) + dimethyl zinc(II) (544-97-8) → 2‐(4‐bromophenyl)‐1,1,1‐trifluoropropan‐2‐ol (122243-28-1)

Conditions	Yield
With titanium tetrachloride In n-heptane; dichloromethane at -40 - 20℃; for 2.08333h;	100%
Stage #1: dimethyl zinc(II) With titanium tetrachloride In n-heptane; dichloromethane at -30℃; for 0.5h; Stage #2: 4'-bromo-2,2,2-trifluoroacetophenone In n-heptane; dichloromethane at -40 - 20℃; for 2h;	100%
Stage #1: dimethyl zinc(II) With titanium tetrachloride In n-heptane; dichloromethane at -30℃; for 0.5h; Stage #2: 4'-bromo-2,2,2-trifluoroacetophenone In n-heptane; dichloromethane at -40 - 20℃; for 2.08333h;	100%

methyl α-(2-methylphenyl)-α-diazoacetate + dimethyl zinc(II) (544-97-8) → (E)-methyl 2-(2-(2-methoxy-2-oxo-1-(o-tolyl)ethylidene)hydrazinyl)-2-(o-tolyl)propanoate

Conditions	Yield
With dirhodium tetraacetate In toluene at 20℃; Inert atmosphere;	100%

2,4a-dimethyl-6-oxo-1a,1b,2,4a,5,5a-hexahydro-1H-2,5-methanocyclopropa[a]-pentalen-3-yl trifluoromethanesulfonate + dimethyl zinc(II) (544-97-8) → 2,3,4a-trimethyl-1a,1b,2,4a,5,5a-hexahydro-1H-2,5-methanocyclopropa[a]pentalen-6-one

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 0℃; for 0.166667h; Negishi Coupling; Inert atmosphere;	100%

dimethyl zinc(II) (544-97-8) + 5-chloro-2-(9,9-difluoro-3,6-dimethyl-9H-fluoren-1-yl)quinoline → 1-bromo-3,6,9,9-tetramethyl-9H-fluorene

Conditions	Yield
With titanium tetrachloride In dichloromethane; toluene at -40 - 20℃; Inert atmosphere;	100%

dimethyl zinc(II) (544-97-8) + 1-bromo-3,6-dimethyl-9H-fluoren-9-one → 1-bromo-3,6,9,9-tetramethyl-9H-fluorene

Conditions	Yield
Stage #1: dimethyl zinc(II) With titanium tetrachloride In toluene at -40℃; for 0.5h; Inert atmosphere; Stage #2: 1-bromo-3,6-dimethyl-9H-fluoren-9-one In dichloromethane; toluene at 20℃; Inert atmosphere;	100%

Upstream product

• 557-20-0 diethylzinc 
• 143-36-2 methylmercury(II) iodide 
• 74-88-4 methyl iodide 
• 557-34-6 zinc diacetate 
• 75-24-1 trimethylaluminum 
• 7440-66-6 zinc 
• 917-54-4 methyllithium 
• 7646-85-7 zinc(II) chloride 
• 7664-41-7 ammonia 
• 74-95-3 1,1-dibromomethane 
• 1000391-90-1 [Zn(Pd(N(FC₆H₃P(C₃H₇)2)2))2] 
• 506-82-1 dimethylcadmium 
• 32955-11-6 ethylzinc(II) iodide 
• 593-74-8 dimethylmercury 

Downstream Products

• 67-63-0 isopropyl alcohol 
• 75-65-0 tert-butyl alcohol 
• 1111-74-6 dimethylsilane 
• 463-82-1 2,2-dimethylpropane 
• 110-12-3 5-Methyl-2-hexanone 
• 79-46-9 2-nitropropane 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 82166-21-0 methyl cyclohexane 
• 591-49-1 1-methylcyclohex-1-ene 
• 590-66-9 1,1-dimethylcyclohexane 
• 13388-93-7 1-(1-methyl-cyclopentyl)-ethanone 
• 99993-30-3 1-tert-butyl-1-methyl-cyclohexane 
• 593-74-8 dimethylmercury 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 

Relevant articles and documents

Selective oxidation of the alkyl ligand in rhenium(V) oxo complexes

Rhenium(V) oxo alkyl triflate compounds (HBpz3)ReO(R)OTf [R = Me (4), Et (5), n-Bu (6); HBpz3 = hydrotris(1-pyrazolyl)borate; OTf = OSO2CF3, triflate] are formed on sequential reaction of (HBpz3)ReOCl2 with dialkyl zinc reagents and AgOTf. These triflate compounds are rapidly oxidized at ambient temperatures by oxygen atom donors pyridine N-oxide (pyO) and dimethyl sulfoxide (DMSO) to give (HBpz3)ReO3 (7) and the corresponding aldehyde. In the cases of 5 and 6 this transformation is quantitative. The addition of 2,6-lutidine to a low-temperature oxidation of 5 by DMSO redirects the reaction to form cis-2-butene instead of acetaldehyde. These oxidation reactions do not proceed through alkoxide intermediates, as shown by independent studies of alkoxide oxidations. Reaction of 5 with pyO or DMSO at -47°C results in the formation of intermediates which are assigned as ylide or 'trapped-carbene' complexes [(HBpz3)ReO(OH){CH(L)CH3}]OTf (L = py (8) or SMe2 (9), respectively). Mechanistic studies and analogies with related systems suggest that oxygen atom transfer to 4-6 forms [(HBpz3)ReO2R]+. Transfer of an α-hydrogen from the alkyl group to an oxo ligand then forms an alkylidene complex which is trapped by SMe2 or py to give the observed intermediates. Further oxidation of the ylide complex gives the aldehyde.

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Molecular Zinc Species with Ge-Zn and Sn-Zn Bonds: A Reversible Insertion of a Stannylene into a Zinc-Carbon Bond

The tetrylenes Ge(ArMe6)2 and Sn(ArMe6)2 (ArMe6 = C6H3-2,6-(C6H2-2,4,6-(CH3)3)2) reacted with dimethylzinc to afford the insertion products (ArMe6)2Ge(Me)ZnMe (1) and (ArMe6)2Sn(Me)ZnMe (3), which feature Ge-Zn and Sn-Zn bonds as well as two-coordinate zinc atoms. Crystals of 1 were found to be unsuitable for X-ray crystallography, so the ethyl-substituted (ArMe6)2Ge(Et)ZnEt (2) was synthesized in a parallel way to provide crystals suitable for X-ray studies. These showed the structure to be similar to that of 3. The reaction of Pb(ArMe6)2 with dimethylzinc yielded ArMe6ZnMe with a linearly coordinated zinc atom via ligand exchange but no characterizable, new lead product was obtained. The reaction of Sn(ArMe6)2 with dimethylzinc is reversible in hydrocarbon solution at room temperature and displayed a dissociation constant Kdiss and a ΔGdiss of 0.0028(5) and 14(4) kJ mol-1 at 298 K, respectively. Compounds 1-4 were characterized by NMR and IR spectroscopy as well as by X-ray crystallography for 1, 3, and 4.

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.