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557-20-0

Basic Information
CAS No.: 557-20-0
Name: Zinc, diethyl-
Molecular Structure:
Molecular Structure of 557-20-0 (Zinc, diethyl-)
Formula: C4H10Zn
Molecular Weight: 123.51
Synonyms: HSDB 929;Zinc ethide;Diethylzinc;
EINECS: 209-161-3
Density: 0.726 g/cm3
Melting Point: -39--28 °C
Boiling Point: 118 °C
Flash Point: -40 °C
Solubility: Reacts violently with water
Appearance: Clear, colorless liquid
Hazard Symbols: FlammableF,HarmfulXn,DangerousN,CorrosiveC
Risk Codes: 14-17-34-50/53-67-65-62-48/20-11-51/53-14/15-63
Safety: 26-45-61-62-8-36/37/39-16-60-43
Transport Information: UN 3399 4.3/PG 1
PSA: 0.00000
LogP: 1.94530
Synthetic route
97-93-8

triethylaluminum

7646-85-7

zinc(II) chloride

557-20-0

diethylzinc

Conditions
ConditionsYield
In neat (no solvent) Sonication; (N2), ZnCl2 introduced into a flask connected to a condenser containingalcohol at -20°C, Et3Al (Et3Al/ZnCl2 2.2) dropped into flask over 10 min at room temp., stirred and heated at 100°C for 1 hed forfurther 20 min; distd.; NMR;86%
In neat (no solvent) Sonication; (N2), ZnCl2 introduced into a flask connected to a condenser containingalcohol at -20°C, Et3Al (Et3Al/ZnCl2 2.4) dropped into flask over 10 min at room temp., stirred and heated at 100°C for 1 hed forfurther 20 min; distd.; NMR;85.2%
In neat (no solvent) Sonication; (N2), ZnCl2 introduced into a flask connected to a condenser containingalcohol at -20°C, Et3Al (Et3Al/ZnCl2 2.6) dropped into flask over 10 min at room temp., stirred and heated at 100°C for 1 hed forfurther 20 min; distd.; NMR;81.1%
74-96-4

ethyl bromide

557-20-0

diethylzinc

Conditions
ConditionsYield
With copper(l) iodide; ethylzinc bromide In neat (no solvent) CuI, Zn were placed in reactor, evacuated for 10 min, filled with Ar, ligand and EtZnBr were added, heated to 38-40°C for 4.5 h, cooled to room temp.; vac. distilled;82%
13824-25-4, 14002-28-9

triethyl-alane; compound with diethyl ether

7646-85-7

zinc(II) chloride

557-20-0

diethylzinc

Conditions
ConditionsYield
In neat (no solvent) Sonication; (N2), ZnCl2 introduced into a flask connected to a condenser containingalcohol at -20°C, Et3Al*Et2O (Et3Al*Et2O/ZnCl2 2.6) dropped intoflask over 10 min at room temp., stirred and heated at 100°C for1 hed for further 20 min; distd.; NMR;82%
In neat (no solvent) Sonication; (N2), ZnCl2 introduced into a flask connected to a condenser containingalcohol at -20°C, Et3Al*Et2O (Et3Al*Et2O/ZnCl2 2.2) dropped intoflask over 10 min at room temp., stirred and heated at 100°C for1 hed for further 20 min; distd.; NMR;80%
In neat (no solvent) Sonication; (N2), ZnCl2 introduced into a flask connected to a condenser containingalcohol at -20°C, Et3Al*Et2O (Et3Al*Et2O/ZnCl2 2.4) dropped intoflask over 10 min at room temp., stirred and heated at 100°C for1 hed for further 20 min; distd.; NMR;80.5%
811-49-4

ethyllithium

7646-85-7

zinc(II) chloride

557-20-0

diethylzinc

Conditions
ConditionsYield
In diethyl ether at -10 - -5℃; for 10h; Large scale;81%
In not given treatment of (ethyl)Li with 0.5 equiv. of ZnCl2;
3840-71-9

2-acetoxy-3,3-dimethyl-but-1-ene

15860-82-9

EtZnOMe

zinc pivaloylacetonate EtZnOMe complex

B

557-20-0

diethylzinc

Conditions
ConditionsYield
In benzene byproducts: methyl acetate; under N2, soln. of EtZnOMe and CH3COOC(t-Bu)CH2 in C6H6 slowly heated to 60°C for 1 h; volatiles (methyl acetate, Et2Zn) removed, residue dissolved in pentane, cooled to -30°C;A 20%
B n/a
74-96-4

ethyl bromide

557-20-0

diethylzinc

Conditions
ConditionsYield
With coppered zinc
925-90-6

ethylmagnesium bromide

ethyl zinc iodide

557-20-0

diethylzinc

2386-64-3

ethylmagnesium chloride

557-20-0

diethylzinc

Conditions
ConditionsYield
With zinc(II) chloride
15106-84-0

ethyl-isobutyl zinc

557-20-0

diethylzinc

Conditions
ConditionsYield
at 25℃; Geschwindikeit der Umlagerung;
627-44-1

diethylmercury

557-20-0

diethylzinc

Conditions
ConditionsYield
With zinc at 100℃;
74-96-4

ethyl bromide

75-03-6

ethyl iodide

557-20-0

diethylzinc

Conditions
ConditionsYield
With coppered zinc
With zinc copper
75-03-6

ethyl iodide

557-20-0

diethylzinc

Conditions
ConditionsYield
With zinc ueber mehrere Stufen;
With zinc at 150 - 160℃;
With diethyl ether; zinc at 130℃; Destillation des Reaktionsproduktes;
60-29-7

diethyl ether

ethylmagnesium bromide

999-75-7

ethylzinc iodide

557-20-0

diethylzinc

925-90-6

ethylmagnesium bromide

999-75-7

ethylzinc iodide

557-20-0

diethylzinc

Conditions
ConditionsYield
With diethyl ether
2025-56-1

ethyl radical

zinc

zinc

557-20-0

diethylzinc

ethyl-radicals

ethyl-radicals

557-20-0

diethylzinc

Conditions
ConditionsYield
With zinc
627-44-1

diethylmercury

zinc

zinc

A

557-20-0

diethylzinc

B

mercury

mercury

Conditions
ConditionsYield
at 100℃; aehnlich wirken Cadmium und Wismut;

ethyl sodium ; compound with diethyl zinc

mercury

mercury

zinc

zinc

A

557-20-0

diethylzinc

B

sodium amalgam

sodium amalgam

ethyl zinc iodide

A

557-20-0

diethylzinc

B

zinc iodide

zinc iodide

Conditions
ConditionsYield
bei der Destillation in CO2-Strom;
75-03-6

ethyl iodide

A

557-20-0

diethylzinc

B

ZnI2

ZnI2

Conditions
ConditionsYield
With zinc entsteht zunaechst Aethylzinkjodid, welches durch Destillation zersetzt;
75-03-6

ethyl iodide

A

557-20-0

diethylzinc

B

zinc(II) iodide

Conditions
ConditionsYield
ethyl iodide, heated with granulated Zn and Zn dust at 80 up to 96°C, is forming ZnEt2 and ZnI2;;

{(ZnEt)2((2-(6-methyl)pyridyl)trimethylsilylamido)2}

A

{Zn((2-(6-methyl)pyridyl)trimethylsilylamido)2}

B

557-20-0

diethylzinc

Conditions
ConditionsYield
In neat (no solvent) Ar-atmosphere; 134°C, 0.10 torr (attempted sublimation);

Zn(C2H5)(C9H23N3)(1+)*C5H(C6H5)4(1-)=Zn(C2H5)(C9H23N3)C5H(C6H5)4

54773-23-8

dineopentylzinc

A

Zn(C5H11)(C9H23N3)(1+)*C5H(C6H5)4(1-)=Zn(C5H11)(C9H23N3)C5H(C6H5)4

B

557-20-0

diethylzinc

Conditions
ConditionsYield
In benzene-d6 Kinetics; stirred for a few min, left standing in NMR tube at 22°C for 1 h; reversible reaction; not isolated; (1)H NMR spectral data;
2386-64-3

ethylmagnesium chloride

zinc dibromide

557-20-0

diethylzinc

Conditions
ConditionsYield
Stage #1: zinc dibromide With sodium methylate In diethyl ether at 0 - 20℃; for 0.416667 - 0.583333h;
Stage #2: ethylmagnesium chloride In diethyl ether at 0 - 20℃; for 2.08333 - 2.16667h; Product distribution / selectivity;
925-90-6

ethylmagnesium bromide

1184-55-0

zinc dimethoxide

557-20-0

diethylzinc

Conditions
ConditionsYield
In diethyl ether Product distribution / selectivity;
Stage #1: zinc dimethoxide With sodium methylate In diethyl ether at 0 - 20℃; for 0.166667 - 0.5h;
Stage #2: ethylmagnesium bromide In diethyl ether at 0 - 20℃; for 2.08333 - 2.16667h; Product distribution / selectivity;
Stage #1: zinc dimethoxide With sodium benzoate In diethyl ether at 0 - 20℃; for 0.166667 - 0.5h;
Stage #2: ethylmagnesium bromide In diethyl ether at 0 - 20℃; for 2.08333 - 2.16667h; Product distribution / selectivity;

zinc diacrylate

2386-64-3

ethylmagnesium chloride

557-20-0

diethylzinc

Conditions
ConditionsYield
In diethyl ether Product distribution / selectivity;
2386-64-3

ethylmagnesium chloride

7646-85-7

zinc(II) chloride

557-20-0

diethylzinc

Conditions
ConditionsYield
In diethyl ether Product distribution / selectivity;
Stage #1: zinc(II) chloride With sodium methylate In diethyl ether at 0 - 20℃; for 0.416667 - 0.583333h;
Stage #2: ethylmagnesium chloride In diethyl ether at 0 - 20℃; for 2.08333 - 2.16667h; Product distribution / selectivity;
557-34-6

zinc diacetate

2386-64-3

ethylmagnesium chloride

557-20-0

diethylzinc

Conditions
ConditionsYield
In diethyl ether Product distribution / selectivity;
2386-64-3

ethylmagnesium chloride

553-72-0

zinc benzoate

557-20-0

diethylzinc

Conditions
ConditionsYield
In diethyl ether Product distribution / selectivity;
930-68-7

cyclohexenone

557-20-0

diethylzinc

Conditions
ConditionsYield
With copper(l) iodide; C19H19N2O2P In dichloromethane at -20℃; for 12h;100%
With N-benzylbenzenesulfonamide In toluene at 0℃; for 1h;99%
copper(I) 2-[(R)-Me2NCH2]-5-(Me3Si)-benzenethiolate In diethyl ether; hexane at -20℃; for 4h; Michael addition;99%
613-69-4

2-ethoxylbenzaldehyde

557-20-0

diethylzinc

A

105836-16-6

(R)-1-(2-ethoxyphenyl)-1-propanol

B

124176-00-7

(S)-1-(2-ethoxyphenyl)-1-propanol

Conditions
ConditionsYield
Zn(II) complex with chiral Lewis acid-Lewis base ligand In toluene at 20℃; for 3h;A n/a
B 100%
With Quinine In toluene Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With N-ethyl (3S)-3-diphenylhydroxymethyl-2-azabicyclo<2.2.2>octane In hexane; toluene for 7h; Ambient temperature; Yield given. Yields of byproduct given;
557-20-0

diethylzinc

104-87-0

4-methyl-benzaldehyde

25574-04-3, 112777-65-8, 138809-38-8, 73854-03-2

(S)-1-(4-methylphenyl)propan-1-ol

Conditions
ConditionsYield
(1S)-1-(9-piperidylfluoren-9-yl)ethanol In hexane; toluene at 0℃; for 4h; Addition;100%
Stage #1: diethylzinc In toluene at 0℃; for 0.5h;
Stage #2: 4-methyl-benzaldehyde In toluene at 0 - 20℃; for 48h; Reagent/catalyst; enantioselective reaction;
99%
Stage #1: diethylzinc; 4-methyl-benzaldehyde With diphenyl-((S)-1-((S)-1-phenylethyl)aziridin-2-yl)-methanol In hexane; toluene at 0 - 25℃; for 48.5h; Inert atmosphere;
Stage #2: With ammonium chloride In hexane; water; toluene Saturated solution; optical yield given as %ee; enantioselective reaction;
98%
557-20-0

diethylzinc

104-88-1

4-chlorobenzaldehyde

110611-21-7

(R)-1-(4-chlorophenyl)-1-propanol

Conditions
ConditionsYield
Stage #1: diethylzinc With (Ra)-3,3'-bis(diphenylphosphinoyl)-BINOL In tetrahydrofuran; toluene at -78℃; for 0.5h;
Stage #2: 4-chlorobenzaldehyde In tetrahydrofuran; toluene at -20℃; for 24h;
100%
(1R,2S)-(-)-1-phenyl-2-piperidinopropane-1-thiol In toluene at 0℃; for 12h;99%
With 1,1-diethyl-3-(3'-indolyl)-(2S)-(N-methyl-N-3'',3''-dimethylbutylamino)-1-propanol In hexane; toluene at 20℃; for 96h; Addition;99%
557-20-0

diethylzinc

104-88-1

4-chlorobenzaldehyde

73890-73-0

(S)-1-(4-chlorophenyl)-1-propanol

Conditions
ConditionsYield
R,S-1,2-disubstituted ferrocenyl amino alcohol 8o In hexane for 1h; Ambient temperature;100%
With (R,R)-(2,4,6-Me3C6H2-CH=N-CH(Ph))2; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane 1.) -78 deg C, 4 h, 2.) -20 deg, 1 h;99%
With 2-tert-butyl-6-((2S,4S,5R)-3,4-dimethyl-5-phenyloxazolidyn-2-yl)-4-methylphenol In hexane; toluene at 20℃; for 72h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
557-20-0

diethylzinc

66-77-3

1-naphthaldehyde

Conditions
ConditionsYield
(1R,2S)-(-)-1-phenyl-2-piperidinopropane-1-thiol In toluene at 0℃; for 12h;100%
Stage #1: diethylzinc; 1-naphthaldehyde With diphenyl-((R)-1-((S)-1-phenylethyl)aziridin-2-yl)-methanol In hexane; toluene at 0 - 25℃; for 48.5h; Inert atmosphere;
Stage #2: With ammonium chloride In hexane; water; toluene Saturated solution; optical yield given as %ee; enantioselective reaction;
99%
Stage #1: diethylzinc With (1R,3S)-1-benzyl-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol In hexane; toluene at 0℃; for 0.0833333h;
Stage #2: 1-naphthaldehyde In hexane; toluene at 0℃; for 2h; Catalytic behavior; Reagent/catalyst; Temperature; enantioselective reaction;
99%
557-20-0

diethylzinc

100-52-7

benzaldehyde

1565-74-8

(R)-1-phenyl-1-propanol

Conditions
ConditionsYield
With P-1-(4',6'-dimethyl-2'-hydroxyphenyl)-2-(N,N-di-n-butylaminomethyl)naphthalene In hexane at 20℃; for 16h;100%
titanium(IV) isopropylate; 1,3,5-[(M)-2-(2-HOCH2-1-naphthyl)-3,5-Me2C6H2OCH2]3-benzene In hexane; dichloromethane at 40℃; for 16h;100%
With (1R,2R)-N,N'-bis[(2,4,6-trimethylphenyl)methylene]-1,2-cyclohexane-diamine; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane at -78 - -20℃; for 5h;100%
557-20-0

diethylzinc

100-52-7

benzaldehyde

613-87-6

(S)-1-phenyl-1-propanol

Conditions
ConditionsYield
(1S,2R)-(-)-2-(N,N-di-n-butylamino)-1-phenylpropan-1-ol In hexane 1.) r.t., 20 min; 2.) 0 deg C, 16 h;100%
With (R,R)-(2,4,6-Me3C6H2-CH=N-CH(Ph))2; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane 1.) -78 deg C, 4 h, 2.) -20 deg, 1 h;100%
Stage #1: diethylzinc; benzaldehyde With (1S,2R,3S,5S)-6,6-dimethyl-3-morpholinobicyclo[3.1.1]heptan-2-ol; (1R,2S,3R,5R)-6,6-dimethyl-3-morpholinobicyclo[3.1.1]heptan-2-ol In hexane at -15 - 0℃; for 18h; Inert atmosphere;
Stage #2: With water; ammonium chloride In hexane at 0℃; optical yield given as %ee; enantioselective reaction;
100%
557-20-0

diethylzinc

123-11-5

4-methoxy-benzaldehyde

105836-14-4

(R)-1-(4'-methoxyphenyl)-1-propanol

Conditions
ConditionsYield
With (1R,2R)-N,N'-bis[(2,4,6-trimethylphenyl)methylene]-1,2-cyclohexane-diamine; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane at -78 - -20℃; for 5h;100%
Stage #1: diethylzinc; 4-methoxy-benzaldehyde With (2R,3S,3aS,4aR,6R,8aS)-2-isopropyl-6,9,9-trimethyl-3-phenyldecahydro-4aH-pyrrolo[2,1-b][1,3]benzoxazin-3-ol In hexane; toluene at 20℃; Inert atmosphere;
Stage #2: With ammonium chloride In hexane; water; toluene optical yield given as %ee; enantioselective reaction;
99%
Stage #1: diethylzinc With polystyrene supported nickel(II) complexes derived from α-amino amides In toluene at 0℃; for 0.166667h; Green chemistry;
Stage #2: 4-methoxy-benzaldehyde In toluene at 0℃; for 36h; Inert atmosphere; Green chemistry; enantioselective reaction;
98%
557-20-0

diethylzinc

135-02-4

ortho-anisaldehyde

7452-01-9, 105836-13-3, 123879-92-5, 114389-71-8

(-)-(S)-1-(o-methoxyphenyl)propanol

Conditions
ConditionsYield
(1S,2R)-(-)-2-(N,N-di-n-butylamino)-1-phenylpropan-1-ol In hexane 1.) r.t., 20 min; 2.) 0 deg C, 16 h;100%
Stage #1: diethylzinc; ortho-anisaldehyde With diphenyl-((S)-1-((S)-1-phenylethyl)aziridin-2-yl)-methanol In hexane; toluene at 0 - 25℃; for 48.5h; Inert atmosphere;
Stage #2: With ammonium chloride In hexane; water; toluene Saturated solution; optical yield given as %ee; enantioselective reaction;
99%
With dibutylamino thioacetate derivative of (+)-norephedrine In hexane at 0 - 20℃; for 6h;97%
5153-67-3

nitrostyrene

557-20-0

diethylzinc

119880-63-6, 7796-78-3

(1-nitromethyl-propyl)-benzene

Conditions
ConditionsYield
With chiral (OCHPhCHMeN(i-Pr))PNMe2; copper(I) triflate In hexane; toluene at -30℃; for 3h; Addition;100%
copper(I) 2-(Me2NCH2)-3-(Me3Si)-naphthalene-1-thiolate In diethyl ether; hexane at -20℃; for 4h; Michael addition;98%
With magnesium bromide In diethyl ether for 1h; Ambient temperature;92%
557-20-0

diethylzinc

123-11-5

4-methoxy-benzaldehyde

5349-60-0

1-(4-methoxyphenyl)-1-propanol

Conditions
ConditionsYield
With (R,R)-(2,4,6-Me3C6H2-CH=N-CH(Ph))2; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane 1.) -78 deg C, 4 h, 2.) -20 deg, 1 h;100%
With titanium(IV) isopropylate; (1R,2R)-(+)-1,2-(3,3',5,5'-tetrachloro-2,2'-dihydroxydibenzosulfonamido)cyclohexane In hexane at -23℃;98%
With (-)-η5-(pentamethylcyclopentadienyl)-η5-(2-((2-hydroxy-2,2-diphenylethyl)oxymethyl)pyrrolyl)iron In toluene Ambient temperature;94%
613-69-4

2-ethoxylbenzaldehyde

557-20-0

diethylzinc

105836-16-6

(R)-1-(2-ethoxyphenyl)-1-propanol

Conditions
ConditionsYield
With (1R,3S,4S)-2-<(R)-1-phenylethyl>-2-azabicyclo<2.2.1>heptane-3-exo-methanethiol In hexane; toluene for 7h; Ambient temperature;100%
930-68-7

cyclohexenone

557-20-0

diethylzinc

Conditions
ConditionsYield
With copper(I) thiophene-2-carboxylate; chiral biphenol P-N ligand In diethyl ether100%
With copper(II) bis(trifluoromethanesulfonate); (11aR)-(+)-10,11,12,13-tetrahydrodiindeno[7,1-de:1', 7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine In toluene at 25℃; for 2h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures;99%
With copper(I) trifluoromethanesulfonate benzene; bis[(S,S)-H8-BINOL][(S)-BINOL]diphosphite In diethyl ether at -30℃; for 15h;99%
557-20-0

diethylzinc

Acetic acid (2R,4S,6R)-2-tert-butyl-6-hexyl-[1,3]dioxan-4-yl ester

(2R*,4S*,6S*)-2-tert-butyl-4-ethyl-6-hexyl-1,3-dioxane

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In diethyl ether at -78℃; for 1h;100%
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 0.6h;90%
557-20-0

diethylzinc

459-57-4

4-fluorobenzaldehyde

(S)-1-(4-fluorophenyl)propanol

Conditions
ConditionsYield
(1S)-1-(9-piperidylfluoren-9-yl)ethanol In hexane; toluene at 0℃; for 4h; Addition;100%
Stage #1: diethylzinc In toluene at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 4-fluorobenzaldehyde In toluene at 0℃; for 6h; Inert atmosphere;
Stage #3: With ammonium chloride In water; toluene at 0℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
92%
Stage #1: diethylzinc With (Sa)-1-[2-diphenylhydroxymethyl-6-(trifluoromethyl)phenyl]-2-(1-pyrrolidinomethyl)-1H-pyrrole In hexane at 20℃; for 1h; Inert atmosphere;
Stage #2: 4-fluorobenzaldehyde In hexane at 0℃; for 16h; Inert atmosphere; enantioselective reaction;
91%
557-20-0

diethylzinc

587-04-2

3-Chlorobenzaldehyde

172748-80-0

(S)-1-(3-chlorophenyl)propan-1-ol

Conditions
ConditionsYield
(1S)-1-(9-piperidylfluoren-9-yl)ethanol In hexane; toluene at 0℃; for 4h; Addition;100%
Stage #1: diethylzinc With 2,2'-(propane-2,2-diyl)bis(6,6-dimethyl-5,6,7,8-tetrahydro-5,7-methanoquinoline-8,2-diyl)bis(diphenylmethanol) In toluene at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: m-Chlorobenzaldehyde In toluene at -20℃; for 57h; Inert atmosphere; enantioselective reaction;
99%
Stage #1: diethylzinc With (1'R,2R,3R)-1-(1'-phenylethyl)-2-phenyl-3-hydroxyazetidine In toluene at 20℃; for 0.333333h;
Stage #2: m-Chlorobenzaldehyde In toluene at 20℃; for 29h; Inert atmosphere; enantioselective reaction;
98%
1462-12-0

diethyl ethylidenemalonate

557-20-0

diethylzinc

83-27-2

sec-butyl-malonic acid diethyl ester

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate); (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In hexane; toluene at 0℃; for 3h;100%
With copper(II) bis(trifluoromethanesulfonate); triethyl phosphite In hexane; toluene -20 deg C and 20 min, 0 deg C;95%
557-20-0

diethylzinc

614-47-1

1,3-diphenyl-propen-3-one

Conditions
ConditionsYield
With copper(I) trifluoromethanesulfonate benzene complex In diethyl ether; hexane at -20℃; for 22h; Michael addition;100%
With copper(II) choride dihydrate; (o-hydroxyphenyl)diphenylphosphine In tetrahydrofuran at -20℃; for 2h;98%
With 3,7-bis[(1'S,2'R)-2'-OH-1'-Me-2'-PhEt]-3,7-diaza-C7H12N2; bis(acetylacetonate)nickel(II) In hexane; acetonitrile at -30℃; for 16h; Addition;96%
557-20-0

diethylzinc

591-31-1

3-methoxy-benzaldehyde

134677-28-4

(1S)-1-(3-methoxyphenyl)propan-1-ol

Conditions
ConditionsYield
(1S)-1-(9-piperidylfluoren-9-yl)ethanol In hexane; toluene at 0℃; for 4h; Addition;100%
Stage #1: diethylzinc In toluene at 0℃; for 0.5h;
Stage #2: 3-methoxy-benzaldehyde In toluene at 0 - 20℃; for 48h; Reagent/catalyst; enantioselective reaction;
99%
With (3S,4S)-2,2-dimethyl-4-[N-(9'-phenylfluoren-9'-yl)amino]pentan-3-ol In hexane; toluene at 18℃; for 1h; Addition;97%
557-20-0

diethylzinc

620-23-5

m-tolyl aldehyde

213267-92-6

(S)-1-(3-methylphenyl)propan-1-ol

Conditions
ConditionsYield
(1S)-1-(9-piperidylfluoren-9-yl)ethanol In hexane; toluene at 0℃; for 4h; Addition;100%
Stage #1: diethylzinc With 2,2'-(propane-2,2-diyl)bis(6,6-dimethyl-5,6,7,8-tetrahydro-5,7-methanoquinoline-8,2-diyl)bis(diphenylmethanol) In toluene at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: m-tolyl aldehyde In toluene at -20℃; for 57h; Inert atmosphere; enantioselective reaction;
95%
Stage #1: m-tolyl aldehyde With (E,4R,5S)-N-allyl-5-cyclohexyl-5-hydroxy-4-morpholinopent-2-enamide In toluene at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: diethylzinc In hexane; toluene at 20℃; for 6h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;
95%
939-97-9

4-tert-Butylbenzaldehyde

557-20-0

diethylzinc

127896-25-7

1-(4-tert-butylphenyl)propan-1-ol

Conditions
ConditionsYield
With (R,R)-(2,4,6-Me3C6H2-CH=N-CH(Ph))2; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane 1.) -78 deg C, 4 h, 2.) -20 deg, 1 h;100%
With (1R,2R)-N,N'-bis[(2,4,6-trimethylphenyl)methylene]-1,2-cyclohexane-diamine; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane at -78 - -20℃; for 5h;100%
With titanium(IV) isopropylate at 80℃; for 1h; Time; Inert atmosphere;60 %Chromat.
With magnesium chloride at 80℃; for 0.5h; Reagent/catalyst; Inert atmosphere;24.2 %Chromat.
557-20-0

diethylzinc

591-31-1

3-methoxy-benzaldehyde

52956-27-1

1-(3-methoxyphenyl)propanol

Conditions
ConditionsYield
With (R,R)-(2,4,6-Me3C6H2-CH=N-CH(Ph))2; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane 1.) -78 deg C, 4 h, 2.) -20 deg, 1 h;100%
With (1R,2R)-N,N'-bis[(2,4,6-trimethylphenyl)methylene]-1,2-cyclohexane-diamine; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane at -78 - -20℃; for 5h;100%
Stage #1: diethylzinc With titanium(IV) isopropylate; (1R,2R)-1,2-bis(3,5-dibromophenyl)ethane-1,2-diol In hexane; dichloromethane at 25℃; for 0.333333h; Inert atmosphere;
Stage #2: 3-methoxy-benzaldehyde In hexane; dichloromethane at 0℃; for 24h; Reagent/catalyst; Inert atmosphere;
53%
557-20-0

diethylzinc

300720-95-0

β-nitroacroleine dimethyl acetal

1,1-dimethoxy-2-nitromethyl-butane

Conditions
ConditionsYield
With chiral PhP(OC(2-naphth)2CH(OCMe2O)CHC(2-naphth)22O); copper(II) bis(trifluoromethanesulfonate) In toluene at -30℃; Addition;100%
With racemic 1,1'-bi(2-naphthol) based phosphoramidite; copper(II) bis(trifluoromethanesulfonate) In hexane; toluene at -45℃; for 3h;64%
930-68-7

cyclohexenone

557-20-0

diethylzinc

Conditions
ConditionsYield
With copper(I) thiophene-2-carboxylate; chiral binapthol P-N ligand In diethyl ether100%
With copper(I) bromide dimethylsulfide complex; 2-(diphenylphosphanyl)benzoyl-L-valyl-L-valine methyl ester In diethyl ether at -30℃; for 2h; Product distribution; Further Variations:; Temperatures; Reagents; Solvents;98%
With copper(I) trifluoromethanesulfonate benzene; [(2-PPh2)C6H4CH]-Val-Phe-NH-Bu In toluene at -30℃; for 6h;98%
557-20-0

diethylzinc

620-23-5

m-tolyl aldehyde

32019-31-1, 112777-68-1

(R)-1-(3-tolyl)-1-propanol

Conditions
ConditionsYield
Stage #1: diethylzinc; m-tolyl aldehyde With (1S,2R,3S,5S)-6,6-dimethyl-2-morpholinobicyclo[3.1.1]heptan-3-ol; (1R,2S,3R,5R)-6,6-dimethyl-2-morpholinobicyclo[3.1.1]heptan-3-ol In hexane at -15 - 0℃; for 18h; Inert atmosphere;
Stage #2: With water; ammonium chloride In hexane at 0℃; optical yield given as %ee; enantioselective reaction;
100%
With 4-methyl-N-{[(1S,2S)-2-(pyrrolidin-1-yl)cyclohexyl]methyl}benzenesulfonamide In hexane at 0℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;97%
With titanium(IV) isopropylate In dichloromethane at 0℃;96%
1121-66-0

2-Cyclohepten-1-one

557-20-0

diethylzinc

(R)-3-ethylcycloheptan-1-one

Conditions
ConditionsYield
With chiral binapthol P-N ligand; copper(II) bis(trifluoromethanesulfonate) In toluene100%
With n-butyllithium; C21H29N2O(1+)*F6P(1-); copper(II) bis(trifluoromethanesulfonate) In diethyl ether at 20℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
With copper(I) trifluoromethanesulfonate benzene; [(2-PPh2)C6H4CH]-Val-Phe-NH-Bu In toluene at -30℃; for 12h;98%
557-20-0

diethylzinc

108-24-7

acetic anhydride

78-84-2

isobutyraldehyde

35897-16-6

2-methyl-3-pentyl acetate

Conditions
ConditionsYield
Stage #1: diethylzinc; isobutyraldehyde With (Rp,S)-5-[C6H11-CH(Me)-N=C(Me)]-4-OH-[2.2]paracyclophane In hexane at 0℃; for 14h;
Stage #2: acetic anhydride In hexane at 20℃; for 24h; Further stages.;
100%
557-20-0

diethylzinc

73636-31-4

O-methyl S-ethyl thioladipate

2955-61-5

Methyl 6-oxooctanoate

Conditions
ConditionsYield
With bromine; N,N-dimethyl-formamide; zinc; palladium on activated charcoal In tetrahydrofuran; toluene at 20℃; for 17h; Fukuyama coupling reaction;100%
With bromine; N,N-dimethyl-formamide; zinc; palladium on activated charcoal In tetrahydrofuran; toluene at 20℃; for 17h; Fukuyama coupling reaction;100%
34036-07-2

3,4 difluorobenzaldehyde

557-20-0

diethylzinc

847448-30-0

(S)-1-(3,4-Difluoro-phenyl)-propan-1-ol

Conditions
ConditionsYield
With titanium(IV) isopropylate; N,N’-(1R,2R)-cyclohexane-1,2-diylbis(1,1,1-trifluoromethanesulfonamide) In toluene at -78℃;100%
Stage #1: diethylzinc With titanium(IV) isopropylate; C48H34O4 In diethyl ether; hexane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 3,4 difluorobenzaldehyde In diethyl ether; hexane at 20℃; for 5h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
92%
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  • Casno:

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    Diethylzinc

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    DIMETHYLZINC

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    Diethyl zinc

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    Factory Supply Diethylzinc CAS 557-20-0

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    Zinc, diethyl-

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    Diethylzinc

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  • diethyl-zinCAS NO.:557-20-0

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Chemistry

Molecular Formula:C4H10Zn
Molecular Weight:123.51
EINECS:209-161-3
Density:1.205 g/mL at 25 °C(lit.)
Melting Point:-39--28°C
Boiling Point:118°C
Flash Point:-40°C
Solubility:REACTS VIOLENTLY with water
Storage temp.:0-6°C 
Water Solubility:REACTS VIOLENTLY
Sensitive:Air & Moisture Sensitive
Merck:  14,3131
Appearance:Clear, colorless liquid
liansport Information:UN 1366/3
Properties:Liquid
Diethylzinc's Synonyms: (C2H5)2Zn;diethyl-zin;diethylzine;ZINCDIETHYL;Zinc ethide;ZINC ETHYL;DIETHYLZINC;DIETHYLZINC, CYLINDER WITH 100 G

Uses

Herbicide for weed control in the cropping of papaver somniferum l

Consensus Reports

Reported in EPA TSCA Inventory. Zinc and its compounds are on the Community Right-To-Know List.

Safety Profile

Presumed to be a poison. Ignites spontaneously in air. Dangerously flammable by spontaneous chemical reaction in air, or with oxidizing materials. A dangerous explosion hazard. Explosive reaction with alkenes + diiodomethane, sulfur dioxide. Reacts violently with bromine, water, nitro compounds. Ignites on contact with air, ozone, methanol, or hydrazine. Reacts violently with nonmetal halides (e.g., arsenic trichloride or phosphorus trichloride) to produce pyrophoric triethyl arsine or triethyl phosphine. To fight fire, do not use water, foam, or halogenated extinguishing agents. Use dry materials, such as graphite, sand, etc. When heated to decomposition it emits toxic fumes of ZnO. See also ZINC COMPOUNDS.

Diethylzinc's Safety Information
Hazard Codes  F,Xn,N,C
RIDADR  UN 3399 4.3/PG 1
WGK Germany  2
RTECS  ZH2077777
F  10-23
TSCA  Yes
HazardClass  4.3

EC Risk Phrase 21/22 50/53
EC Safety Phrase 36/37 60 61
PackingGroup  I

Standards and Recommendations

DOT Classification:  4.2; Label: Spontaneously Combustible

Specification

Diethylzinc's Hazards Identification 
【Inhalation】Material may be irritating to mucous membranes and upper respiratory tract. May be harmful if inhaled.
【Skin】May cause skin irritation. Harmful if absorbed through skin.
【Eyes】May cause eye irritation.
【Ingestion】Harmful if swallowed.
【Hazards】Emits toxic fumes under fire conditions.
【UN (DOT)】2810