DIETHYLZINC supplier | CasNO.557-20-0

Name
Diethylzinc
EINECS 209-161-3
CAS No. 557-20-0
Article Data57
CAS DataBase
Density 0.726 g/cm³
Solubility Reacts violently with water
Melting Point -39--28 °C
Formula C₄H₁₀Zn
Boiling Point 118 °C
Molecular Weight 123.513
Flash Point -40 °C
Transport Information UN 3399 4.3/PG 1
Appearance Clear, colorless liquid
Safety 26-45-61-62-8-36/37/39-16-60-43
Risk Codes 14-17-34-50/53-67-65-62-48/20-11-51/53-14/15-63
Molecular Structure
Hazard Symbols F,Xn,N,C
Synonyms HSDB 929;Zinc ethide;Diethylzinc;
PSA 0.00000
LogP 1.94530

Synthetic route

: 97-93-8
triethylaluminum

: 7646-85-7
zinc(II) chloride

: 557-20-0
diethylzinc

Conditions

Conditions	Yield
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

: 7440-66-6
zinc

: 557-20-0
diethylzinc

Conditions

Conditions	Yield
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

Conditions	Yield
In neat (no solvent) Sonication; (N2), ZnCl2 introduced into a flask connected to a condenser containingalcohol at -20°C, Et3AlEt2O (Et3AlEt2O/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, Et3AlEt2O (Et3AlEt2O/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, Et3AlEt2O (Et3AlEt2O/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

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 74-96-4
ethyl bromide

: 557-20-0
diethylzinc

Conditions

Conditions	Yield
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

Conditions	Yield
With zinc(II) chloride

: 15106-84-0
ethyl-isobutyl zinc

: 557-20-0
diethylzinc

Conditions

Conditions	Yield
at 25℃; Geschwindikeit der Umlagerung;

: 627-44-1
diethylmercury

: 557-20-0
diethylzinc

Conditions

Conditions	Yield
With zinc at 100℃;

: 74-96-4
ethyl bromide

: 75-03-6
ethyl iodide

: 557-20-0
diethylzinc

Conditions

Conditions	Yield
With coppered zinc
With zinc copper

: 75-03-6
ethyl iodide

: 557-20-0
diethylzinc

Conditions

Conditions	Yield
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

...Expand

: 925-90-6
ethylmagnesium bromide

: 999-75-7
ethylzinc iodide

: 557-20-0
diethylzinc

Conditions

Conditions	Yield
With diethyl ether

: 2025-56-1
ethyl radical

zinc: zinc

: 557-20-0
diethylzinc

ethyl-radicals: ethyl-radicals

: 557-20-0
diethylzinc

Conditions

Conditions	Yield
With zinc

: 627-44-1
diethylmercury

zinc: zinc

A: 557-20-0
diethylzinc

B mercury: mercury

Conditions

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

...Expand

: ethyl sodium ; compound with diethyl zinc

mercury: mercury

zinc: zinc

A: 557-20-0
diethylzinc

B sodium amalgam: sodium amalgam

...Expand

: ethyl zinc iodide

A: 557-20-0
diethylzinc

B zinc iodide: zinc iodide

Conditions

Conditions	Yield
bei der Destillation in CO2-Strom;

: 75-03-6
ethyl iodide

A: 557-20-0
diethylzinc

B ZnI2: ZnI2

Conditions

Conditions	Yield
With zinc entsteht zunaechst Aethylzinkjodid, welches durch Destillation zersetzt;

: 75-03-6
ethyl iodide

: 7440-66-6
zinc

A: 557-20-0
diethylzinc

B: zinc(II) iodide

Conditions

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

...Expand

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

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

B: 557-20-0
diethylzinc

Conditions

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 2386-64-3
ethylmagnesium chloride

: zinc dibromide

: 557-20-0
diethylzinc

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In diethyl ether Product distribution / selectivity;

: 2386-64-3
ethylmagnesium chloride

: 7646-85-7
zinc(II) chloride

: 557-20-0
diethylzinc

Conditions

Conditions	Yield
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

Conditions	Yield
In diethyl ether Product distribution / selectivity;

: 2386-64-3
ethylmagnesium chloride

: 553-72-0
zinc benzoate

: 557-20-0
diethylzinc

Conditions

Conditions	Yield
In diethyl ether Product distribution / selectivity;

: 930-68-7
cyclohexenone

: 557-20-0
diethylzinc

: 64847-85-4, 74006-73-8, 74006-74-9, 22461-89-8
3-ethyl cyclohexanone

Conditions

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 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

Conditions	Yield
(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

Conditions	Yield
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

Conditions	Yield
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

: 56620-47-4, 77495-17-1, 135818-31-4, 114091-67-7
(R)-1-(1-naphthyl)propanol

Conditions

Conditions	Yield
(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

Conditions	Yield
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

Conditions	Yield
(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

Conditions	Yield
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

Conditions	Yield
(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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

: 22461-89-8, 64847-85-4, 74006-74-9, 74006-73-8
3-ethylcyclohexanone

Conditions

Conditions	Yield
With copper(I) thiophene-2-carboxylate; chiral biphenol P-N ligand In diethyl ether	100%
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

Conditions	Yield
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

Conditions	Yield
(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

Conditions	Yield
(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

Conditions	Yield
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

: 16460-86-9, 76156-05-3, 115730-45-5, 1454-61-1
1,3-diphenylpentan-1-one

Conditions

Conditions	Yield
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

Conditions	Yield
(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

Conditions	Yield
(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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

: 22461-89-8, 64847-85-4, 74006-73-8, 74006-74-9
(R)-3-ethylcyclohexanone

Conditions

Conditions	Yield
With copper(I) thiophene-2-carboxylate; chiral binapthol P-N ligand In diethyl ether	100%
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

Conditions	Yield
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

Conditions	Yield
With chiral binapthol P-N ligand; copper(II) bis(trifluoromethanesulfonate) In toluene	100%
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

Conditions	Yield
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%

...Expand

: 557-20-0
diethylzinc

: 73636-31-4
O-methyl S-ethyl thioladipate

: 2955-61-5
Methyl 6-oxooctanoate

Conditions

Conditions	Yield
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

Conditions	Yield
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%

DIETHYLZINC Chemical Properties

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

DIETHYLZINC Uses

Herbicide for weed control in the cropping of papaver somniferum l

DIETHYLZINC Consensus Reports

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

DIETHYLZINC 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

DIETHYLZINC Standards and Recommendations

DOT Classification: 4.2; Label: Spontaneously Combustible

DIETHYLZINC 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

Product Name

Diethylzinc

Synthetic route

DIETHYLZINC Chemical Properties

DIETHYLZINC Uses

DIETHYLZINC Consensus Reports

DIETHYLZINC Safety Profile

DIETHYLZINC Standards and Recommendations

DIETHYLZINC Specification

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