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Diethylzinc Manufacturer/High quality/Best price/In stock
Cas No: 557-20-0
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
Diethylzinc
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USD $ 1.0-2.0 / Metric Ton 1 Metric Ton 100 Metric Ton/Week Hebei yanxi chemical co.,LTD. Contact Supplier
Diethyl zinc
Cas No: 557-20-0
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DIMETHYLZINC
Cas No: 557-20-0
No Data 1 Gram 20 Metric Ton/Week Henan Allgreen Chemical Co.,Ltd Contact Supplier
Factory Supply Diethylzinc
Cas No: 557-20-0
No Data 1 1 Ality Chemical Corporation Contact Supplier
Amadis Chemical offer CAS#557-20-0;CAT#A830770
Cas No: 557-20-0
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier
Zinc, diethyl-
Cas No: 557-20-0
USD $ 100.0-150.0 / Kilogram 1 Kilogram 1000 Metric Ton/Day Wuhan Monad Medicine Tech Co.,LTD Contact Supplier
Diethylzinc CAS:557-20-0
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USD $ 10.0-10.0 / Kilogram 1 Kilogram 800 Metric Ton/Month Hebei Guanlang Biotechnology Co., Ltd. Contact Supplier
Diethylzinc, elec. gr., 99.9995%
Cas No: 557-20-0
No Data No Data 5 Hangzhou J&H Chemical Co., Ltd. Contact Supplier
High quality Diethylzinc
Cas No: 557-20-0
USD $ 100.0-100.0 / Kilogram 1 Kilogram 10000 Kilogram/Day Metric Ton/Day Zibo Hangyu Import&Export Co., Ltd Contact Supplier

557-20-0 Usage

Safety Profile

Presumed to be a poison. Ignites spontaneously in air. Dangerously flammable by spontaneous chemical reaction in air, or with oxidzing materials. A dangerous explosion hazard Explosive reaction with alkenes + diodomethane, sulfur dioxide. Reacts violently with bromine, water, nitro compounds. Igmtes 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.

Uses

Diethyl zinc is used in organic synthesis. It isalso used in preservation of archival papers.

Fire Hazard

Diethylzinc ignites spontaneously in air, burning with a blue flame. Reactions with water and lower alcohols can be violent.Violent reactions can occur with halogens, halogenated hydrocarbons, nitroorganics, oxidizers, sulfur dioxide, and chlorides of phosphorus, arsenic, and antimony. With the latter compounds, diethylzinc forms pyrophoric triethylphosphine, triethyl arsine, and triethylstibine, respectively.

Health Hazard

Being moisture sensitive, any accidental contactof the pure liquid or its concentratedsolution with the skin can cause a severeburn.

Chemical Properties

Clear colorless solution

Reactivity Profile

Diethylzinc is pyrophoric in air, Diethylzinc ignites instantaneously. Diethylzinc reacts explosively with alcohols (methanol, ethanol), bromine, chlorine or liquefied sulfur dioxide [Houben-Weyl, 1973, 13.2a, p. 855, 757, 709]. Reaction with water, nitro compounds, arsenic trichloride, phosphorus trichloride is violent [Bretherick, 5th ed., 1995, p. 587].

Health Hazard

Inhalation of mist or vapor causes immediate irritation of nose and throat; 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., with complete recovery in 24-48 hrs. Eyes are immediately and severely irritated on contact with liquid, vapor, or dilute solution; without thorough irrigation, cornea may be permanently damaged. Moisture in skin combines with chemical to cause thermal and acid burns; tissue may be scarred without prompt treatment. Ingestion is unlikely but would cause immediate burns at site of contact; pain, nausea, vomiting, cramps, and diarrhea may follow; if untreated, tissue may become ulcerated.

Uses

In organic synthesis; in preservation on archival papers.

General Description

Diethylzinc is a pyrophoric liquid with a garlic-like odor. Diethylzinc is stable when Diethylzinc is shipped in sealed tubes with carbon dioxide. Diethylzinc may decompose violently in water and ignite spontaneously with air. Diethylzinc is toxic by ingestion. If exposed to heat or flame, containers of Diethylzinc may explode. Diethylzinc is used as an aircraft fuel.

Air & Water Reactions

Highly flammable. Ignites in air with a blue flame giving off a peculiar garlic-like odor, [Merck, 11th ed., 1989]. Diethyl zinc is spontaneously flammable in air, [Douda(1966)]. Reacts violently with water to form flammable ethane gas, [Brauer(1965)].
InChI:InChI=1/2C2H5.Zn/c2*1-2;/h2*1H2,2H3;/rC4H10Zn/c1-3-5-4-2/h3-4H2,1-2H3

557-20-0 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (D3214)  Diethylzinc (ca. 17% in Hexane, ca. 1mol/L)   557-20-0 100mL 785.00CNY Detail
TCI America (D3214)  Diethylzinc (ca. 17% in Hexane, ca. 1mol/L)   557-20-0 500mL 2,390.00CNY Detail
Alfa Aesar (39564)  Diethylzinc, 96%    557-20-0 100g 2249.0CNY Detail
Alfa Aesar (89038)  Diethylzinc, nominally 15% w/w in hexanes    557-20-0 25g 352.0CNY Detail
Alfa Aesar (89038)  Diethylzinc, nominally 15% w/w in hexanes    557-20-0 100g 1405.0CNY Detail
Alfa Aesar (89038)  Diethylzinc, nominally 15% w/w in hexanes    557-20-0 500g 4409.0CNY Detail
Alfa Aesar (44880)  Diethylzinc, nominally 15% w/w in hexanes, packaged under Argon in resealable ChemSeal? bottles    557-20-0 25g 316.0CNY Detail
Alfa Aesar (44880)  Diethylzinc, nominally 15% w/w in hexanes, packaged under Argon in resealable ChemSeal? bottles    557-20-0 100g 1017.0CNY Detail
Aldrich (406023)  Diethylzincsolution  1.0 M in heptane 557-20-0 406023-100ML 1,378.26CNY Detail
Aldrich (406023)  Diethylzincsolution  1.0 M in heptane 557-20-0 406023-800ML 4,701.06CNY Detail
Aldrich (296112)  Diethylzincsolution  1.0 M in hexanes 557-20-0 296112-100ML 1,242.54CNY Detail
Aldrich (296112)  Diethylzincsolution  1.0 M in hexanes 557-20-0 296112-800ML 4,663.62CNY Detail

557-20-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name diethylzinc

1.2 Other means of identification

Product number -
Other names zinc,ethane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Corrosion inhibitors and anti-scaling agents,Intermediates,Oxidizing/reducing agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:557-20-0 SDS

557-20-0Synthetic route

triethylaluminum
97-93-8

triethylaluminum

zinc(II) chloride
7646-85-7

zinc(II) chloride

diethylzinc
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%
ethyl bromide
74-96-4

ethyl bromide

diethylzinc
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%
triethyl-alane; compound with diethyl ether
13824-25-4, 14002-28-9

triethyl-alane; compound with diethyl ether

zinc(II) chloride
7646-85-7

zinc(II) chloride

diethylzinc
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%
ethyllithium
811-49-4

ethyllithium

zinc(II) chloride
7646-85-7

zinc(II) chloride

diethylzinc
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;
2-acetoxy-3,3-dimethyl-but-1-ene
3840-71-9

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

EtZnOMe
15860-82-9

EtZnOMe

zinc pivaloylacetonate EtZnOMe complex

zinc pivaloylacetonate EtZnOMe complex

B

diethylzinc
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
ethyl bromide
74-96-4

ethyl bromide

diethylzinc
557-20-0

diethylzinc

Conditions
ConditionsYield
With coppered zinc
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

ethyl zinc iodide

ethyl zinc iodide

diethylzinc
557-20-0

diethylzinc

ethylmagnesium chloride
2386-64-3

ethylmagnesium chloride

diethylzinc
557-20-0

diethylzinc

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

ethyl-isobutyl zinc

diethylzinc
557-20-0

diethylzinc

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

diethylmercury

diethylzinc
557-20-0

diethylzinc

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

ethyl bromide

ethyl iodide
75-03-6

ethyl iodide

diethylzinc
557-20-0

diethylzinc

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

ethyl iodide

diethylzinc
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;
diethyl ether
60-29-7

diethyl ether

ethylmagnesium bromide

ethylmagnesium bromide

ethylzinc iodide
999-75-7

ethylzinc iodide

diethylzinc
557-20-0

diethylzinc

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

ethylzinc iodide
999-75-7

ethylzinc iodide

diethylzinc
557-20-0

diethylzinc

Conditions
ConditionsYield
With diethyl ether
ethyl radical
2025-56-1

ethyl radical

zinc

zinc

diethylzinc
557-20-0

diethylzinc

ethyl-radicals

ethyl-radicals

diethylzinc
557-20-0

diethylzinc

Conditions
ConditionsYield
With zinc
diethylmercury
627-44-1

diethylmercury

zinc

zinc

A

diethylzinc
557-20-0

diethylzinc

B

mercury

mercury

Conditions
ConditionsYield
at 100℃; aehnlich wirken Cadmium und Wismut;
ethyl sodium ; compound with diethyl zinc

ethyl sodium ; compound with diethyl zinc

mercury

mercury

zinc

zinc

A

diethylzinc
557-20-0

diethylzinc

B

sodium amalgam

sodium amalgam

ethyl zinc iodide

ethyl zinc iodide

A

diethylzinc
557-20-0

diethylzinc

B

zinc iodide

zinc iodide

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

ethyl iodide

A

diethylzinc
557-20-0

diethylzinc

B

ZnI2

ZnI2

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

ethyl iodide

A

diethylzinc
557-20-0

diethylzinc

B

zinc(II) iodide

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}

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

A

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

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

B

diethylzinc
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

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

dineopentylzinc
54773-23-8

dineopentylzinc

A

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

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

B

diethylzinc
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;
ethylmagnesium chloride
2386-64-3

ethylmagnesium chloride

zinc dibromide

zinc dibromide

diethylzinc
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;
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

zinc dimethoxide
1184-55-0

zinc dimethoxide

diethylzinc
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

zinc diacrylate

ethylmagnesium chloride
2386-64-3

ethylmagnesium chloride

diethylzinc
557-20-0

diethylzinc

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

ethylmagnesium chloride

zinc(II) chloride
7646-85-7

zinc(II) chloride

diethylzinc
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;
zinc diacetate
557-34-6

zinc diacetate

ethylmagnesium chloride
2386-64-3

ethylmagnesium chloride

diethylzinc
557-20-0

diethylzinc

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

ethylmagnesium chloride

zinc benzoate
553-72-0

zinc benzoate

diethylzinc
557-20-0

diethylzinc

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

cyclohexenone

diethylzinc
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%
2-ethoxylbenzaldehyde
613-69-4

2-ethoxylbenzaldehyde

diethylzinc
557-20-0

diethylzinc

A

(R)-1-(2-ethoxyphenyl)-1-propanol
105836-16-6

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

B

(S)-1-(2-ethoxyphenyl)-1-propanol
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;
diethylzinc
557-20-0

diethylzinc

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

(S)-1-(4-methylphenyl)propan-1-ol
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%
diethylzinc
557-20-0

diethylzinc

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

(R)-1-(4-chlorophenyl)-1-propanol
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%
diethylzinc
557-20-0

diethylzinc

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

(S)-1-(4-chlorophenyl)-1-propanol
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%
diethylzinc
557-20-0

diethylzinc

1-naphthaldehyde
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%
diethylzinc
557-20-0

diethylzinc

benzaldehyde
100-52-7

benzaldehyde

(R)-1-phenyl-1-propanol
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%
diethylzinc
557-20-0

diethylzinc

benzaldehyde
100-52-7

benzaldehyde

(S)-1-phenyl-1-propanol
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%
diethylzinc
557-20-0

diethylzinc

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

(R)-1-(4'-methoxyphenyl)-1-propanol
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%
diethylzinc
557-20-0

diethylzinc

ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

(-)-(S)-1-(o-methoxyphenyl)propanol
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%
nitrostyrene
5153-67-3

nitrostyrene

diethylzinc
557-20-0

diethylzinc

(1-nitromethyl-propyl)-benzene
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%
diethylzinc
557-20-0

diethylzinc

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

1-(4-methoxyphenyl)-1-propanol
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%
2-ethoxylbenzaldehyde
613-69-4

2-ethoxylbenzaldehyde

diethylzinc
557-20-0

diethylzinc

(R)-1-(2-ethoxyphenyl)-1-propanol
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%
cyclohexenone
930-68-7

cyclohexenone

diethylzinc
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%
diethylzinc
557-20-0

diethylzinc

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

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

(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%
diethylzinc
557-20-0

diethylzinc

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

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

(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%
diethylzinc
557-20-0

diethylzinc

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

(S)-1-(3-chlorophenyl)propan-1-ol
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%
diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

diethylzinc
557-20-0

diethylzinc

sec-butyl-malonic acid diethyl ester
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%
diethylzinc
557-20-0

diethylzinc

1,3-diphenyl-propen-3-one
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%
diethylzinc
557-20-0

diethylzinc

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

(1S)-1-(3-methoxyphenyl)propan-1-ol
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%
diethylzinc
557-20-0

diethylzinc

m-tolyl aldehyde
620-23-5

m-tolyl aldehyde

(S)-1-(3-methylphenyl)propan-1-ol
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%
4-tert-Butylbenzaldehyde
939-97-9

4-tert-Butylbenzaldehyde

diethylzinc
557-20-0

diethylzinc

1-(4-tert-butylphenyl)propan-1-ol
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.
diethylzinc
557-20-0

diethylzinc

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

1-(3-methoxyphenyl)propanol
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%
diethylzinc
557-20-0

diethylzinc

β-nitroacroleine dimethyl acetal
300720-95-0

β-nitroacroleine dimethyl acetal

1,1-dimethoxy-2-nitromethyl-butane

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%
cyclohexenone
930-68-7

cyclohexenone

diethylzinc
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%
diethylzinc
557-20-0

diethylzinc

m-tolyl aldehyde
620-23-5

m-tolyl aldehyde

(R)-1-(3-tolyl)-1-propanol
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%
2-Cyclohepten-1-one
1121-66-0

2-Cyclohepten-1-one

diethylzinc
557-20-0

diethylzinc

(R)-3-ethylcycloheptan-1-one

(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%
diethylzinc
557-20-0

diethylzinc

acetic anhydride
108-24-7

acetic anhydride

isobutyraldehyde
78-84-2

isobutyraldehyde

2-methyl-3-pentyl acetate
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%
diethylzinc
557-20-0

diethylzinc

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

O-methyl S-ethyl thioladipate

Methyl 6-oxooctanoate
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%
3,4 difluorobenzaldehyde
34036-07-2

3,4 difluorobenzaldehyde

diethylzinc
557-20-0

diethylzinc

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