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589-16-2

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589-16-2 Usage

Chemical Properties

clear yellow to red-brown liquid

Uses

4-Ethylaniline can be used as intermediates of liquid crystal.

Safety Profile

Poison by ingestion, intravenous, and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also N-ETHYLANILINE.

Purification Methods

Dissolve p-ethylaniline in *benzene, then acetylate it. Recrystallise the acetyl derivative (m 93-94o, Hickinbottom & Waine J Chem Soc 1565 1930) from *C6H6/pet ether or EOH, and hydrolyse it by refluxing 50g with 500mL of H2O and 115mL of conc H2SO4 until the solution becomes clear. The amine sulfate is isolated, suspended in H2O and solid KOH is added to generate the free base, which separates. Dry it (KOH), and distil it from zinc dust in a vacuum [Berliner & Berliner J Am Chem Soc 76 6179 1954]. The picrate has m 171-172o (from 1,2-dichloroethane). [Beilstein 12 H 1090, 12 III 2380, 12 IV 2419.]

Check Digit Verification of cas no

The CAS Registry Mumber 589-16-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 9 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 589-16:
(5*5)+(4*8)+(3*9)+(2*1)+(1*6)=92
92 % 10 = 2
So 589-16-2 is a valid CAS Registry Number.
InChI:InChI=1/C8H11N/c1-2-7-3-5-8(9)6-4-7/h3-6H,2,9H2,1H3/p+1

589-16-2 Well-known Company Product Price

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  • Alfa Aesar

  • (B24652)  4-Ethylaniline, 98+%   

  • 589-16-2

  • 100g

  • 431.0CNY

  • Detail
  • Alfa Aesar

  • (B24652)  4-Ethylaniline, 98+%   

  • 589-16-2

  • 500g

  • 1616.0CNY

  • Detail

589-16-2SDS

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 4-Ethylaniline

1.2 Other means of identification

Product number -
Other names Aniline,4-ethyl

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:589-16-2 SDS

589-16-2Synthetic route

4-nitrostyrene
100-13-0

4-nitrostyrene

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h;100%
With hydrogen In ethyl acetate at 20℃; under 7600.51 Torr; for 4h;99%
With 5% Pd/C; hydrogen In ethanol at 20℃; for 0.333333h; chemoselective reaction;98%
4-benzyloxycarbonylaminophenylacetylene
371153-68-3

4-benzyloxycarbonylaminophenylacetylene

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With hydrogen In methanol at 20℃; for 3.5h;100%
With hydrogen In methanol at 40℃; under 760.051 Torr; for 24h; Reagent/catalyst; chemoselective reaction;100%
With hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;98%
With hydrogen In methanol at 40℃; for 24h; chemoselective reaction;89%
With palladium 10% on activated carbon; hydrogen at 20℃; for 24h; Neat (no solvent);84%
4-Ethynylaniline
14235-81-5

4-Ethynylaniline

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 75℃; under 750.075 Torr; Reagent/catalyst; Pressure; Flow reactor;100%
With hydrogen In methanol at 20℃; for 5h; chemoselective reaction;94%
With [Fe(nacnac)dippCH2SiMe3]; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In benzene-d6 at 20℃; for 0.5h; Sealed tube; Inert atmosphere; Schlenk technique; Glovebox;50%
4-benzyloxycarbonylaminophenylacetylene
371153-68-3

4-benzyloxycarbonylaminophenylacetylene

A

N-(benzyloxycarbonyl)-4-ethylaniline
93008-63-0

N-(benzyloxycarbonyl)-4-ethylaniline

B

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 24h; chemoselective reaction;A 100%
B n/a
With palladium 10% on activated carbon; hydrogen In methanol at 25℃; under 750.075 Torr; Flow reactor;
With hydrogen In methanol at 20℃; under 760.051 Torr; for 24h; Reagent/catalyst; chemoselective reaction;
4-ethylnitrobenzene
100-12-9

4-ethylnitrobenzene

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrazine hydrate In ethanol at 20℃; for 12h; Schlenk technique;99%
With borane-ammonia complex In methanol; water at 49.84℃; for 0.1h; Catalytic behavior;99%
With hydrogen In ethanol at 90℃; under 7500.75 Torr; for 2h; Autoclave;99%
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; water; hydrazine hydrate In ethanol at 100℃; for 24h; Reagent/catalyst;99%
With triethylsilane; palladium dichloride In ethanol for 1h; Inert atmosphere; Reflux;94%
Stage #1: (4-nitrophenyl)ethanone With hydrazine hydrate at 135℃; for 3h;
Stage #2: With potassium hydroxide at 135℃; for 24h;
76%
With palladium on carbon; hydrogen In ethanol at 25℃; under 5171.62 Torr; Reagent/catalyst; Sealed tube;99 %Chromat.
With chlorobenzene In methanol at 40℃; for 16h; Sealed tube; Green chemistry; chemoselective reaction;91 %Spectr.
1-azido-4-ethylbenzene
128654-33-1

1-azido-4-ethylbenzene

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With hydrogen In methanol at 25℃; for 3h; Reagent/catalyst; chemoselective reaction;99%
With hydrogen In methanol at 25℃; for 6h; Reagent/catalyst; chemoselective reaction;97%
(4-Nitrophenyl)acetylene
937-31-5

(4-Nitrophenyl)acetylene

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 7h;98%
With sodium tetrahydroborate; copper In tetrahydrofuran; water at 50℃; for 2h;90%
With platinum(IV) oxide; hydrogen In ethanol for 2h;46%
With hydrogen In toluene at 20℃; under 7757.43 Torr; for 6h; Catalytic behavior;
With PdCd0.53; hydrogen In N,N-dimethyl-formamide at 60℃; under 750.075 Torr; Catalytic behavior; Reagent/catalyst; Sealed tube;
4-vinyl benzylamine
1520-21-4

4-vinyl benzylamine

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With iron(III) chloride; lithium aluminium tetrahydride; hydrogen In tetrahydrofuran at 18℃; under 7500.75 Torr; for 20h; Inert atmosphere; Sealed tube;97%
With oxygen; hydrazine hydrate In propan-1-ol at 100℃; under 15001.5 Torr;95%
With oxygen; hydrazine hydrate In propan-1-ol at 100℃; under 15001.5 Torr; for 0.166667h; Flow reactor;95%
4-Ethynylaniline
14235-81-5

4-Ethynylaniline

A

4-vinyl benzylamine
1520-21-4

4-vinyl benzylamine

B

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With hydrogen In hexane; toluene at 30℃; under 760.051 Torr; for 8h;A 95%
B 5%
With hydrogen In 1,4-dioxane at 20℃; for 24h; chemoselective reaction;
With hydrogen In 1,4-dioxane at 85℃; under 4500.45 Torr; for 14h; chemoselective reaction;A 24 %Chromat.
B n/a
With carbon monoxide; hydrogen In tetrahydrofuran at 70℃; under 7757.43 Torr; for 6h; Autoclave;
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

A

4-Aminoacetophenone
99-92-3

4-Aminoacetophenone

B

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With hydrogen In glycerol at 100℃; for 2h;A 95%
B n/a
With methanesulfonic acid; palladium, 5% on calcium carbonate, poisoned with lead; hydrogen In ethanol at 30℃; under 2585.81 Torr; for 22h; Reagent/catalyst; Sealed tube;A 66 %Chromat.
B 26 %Chromat.
4-Aminoacetophenone
99-92-3

4-Aminoacetophenone

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With sodium tetrahydroborate; aluminium trichloride In tetrahydrofuran for 2h; Heating;94%
With sodium hypophosphite monohydrate; 5%-palladium/activated carbon; hypophosphorous acid In water at 20℃; Temperature; Sonication;86%
With hydrogenchloride; amalgamated zinc
1-(4-aminophenyl)ethanol
93453-80-6, 14572-89-5

1-(4-aminophenyl)ethanol

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
Stage #1: 1-(4-aminophenyl)ethanol With ammonium formate In ethanol; water at 22℃; for 0.166667h;
Stage #2: With formic acid In ethanol; water at 22℃; for 1h; chemoselective reaction;
93%
With indium; ammonium chloride In ethanol Heating;31%
With formic acid; 5%-palladium/activated carbon; ammonium formate In methanol; water at 80℃;96 %Spectr.
4-nitrostyrene
100-13-0

4-nitrostyrene

A

4-vinyl benzylamine
1520-21-4

4-vinyl benzylamine

B

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With borane-ammonia complex In ethanol at 20℃; for 0.25h; Reagent/catalyst; Schlenk technique;A 91.53%
B 8.47%
With borane-ammonia complex In methanol at 24.84℃; for 2h; Schlenk technique; Inert atmosphere; Irradiation;A 71%
B 29%
With hydrogenchloride; iron In water for 3h; Reflux; Overall yield = 0.25 g;
bis-(4-ethyl-phenyl)-diazene
61653-33-6

bis-(4-ethyl-phenyl)-diazene

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With perchloric acid In isopropyl alcohol; acetonitrile at 25℃; for 0.7h; pH=2; Inert atmosphere; Irradiation;90%
tert-butyl N-(4-ethylphenyl)carbamate
1220120-57-9

tert-butyl N-(4-ethylphenyl)carbamate

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With 1,1,3,3-Tetramethyldisiloxane; pyrographite; palladium dichloride In 1,2-dimethoxyethane at 25 - 40℃; for 6h;90%
N-benzyloxycarbonyl-4-aminostyrene
227778-64-5

N-benzyloxycarbonyl-4-aminostyrene

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal; ethylenediamine In tetrahydrofuran at 20℃; under 760 Torr; for 16h; Hydrogenation;89%
4-azidoacetophenone
20062-24-2

4-azidoacetophenone

A

1-(4-aminophenyl)ethanol
93453-80-6, 14572-89-5

1-(4-aminophenyl)ethanol

B

4-Aminoacetophenone
99-92-3

4-Aminoacetophenone

C

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 25℃; under 760.051 Torr; for 1.5h;A 5%
B 89%
C 6%
ethyl vinyl ether
109-92-2

ethyl vinyl ether

aniline
62-53-3

aniline

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With zinc(II) chloride In 1,4-dioxane at 100℃; for 12h; Schlenk technique;87%
N-ethyl-N-phenylamine
103-69-5

N-ethyl-N-phenylamine

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With aluminum oxide; aluminium trichloride for 0.05h; microwave irradiation;86%
With cobalt(II) bromide at 230℃; unter vermindertem Druck;
With cobalt(II) chloride at 200 - 270℃;
(4-Nitrophenyl)acetylene
937-31-5

(4-Nitrophenyl)acetylene

A

4-ethylnitrobenzene
100-12-9

4-ethylnitrobenzene

B

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
Stage #1: (4-Nitrophenyl)acetylene With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane at 20℃; for 0.25h; Inert atmosphere;
Stage #2: With formic acid In 1,4-dioxane at 80℃; Inert atmosphere; chemoselective reaction;
A 85%
B 7%
ethane
74-84-0

ethane

aniline
62-53-3

aniline

A

ortho-ethylaniline
578-54-1

ortho-ethylaniline

B

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
In gaseous matrix at 80℃; Irradiation;A 82%
B 18 % Spectr.
In gaseous matrix at 80℃; Irradiation;A 82 % Spectr.
B n/a
triethyl borane
97-94-9

triethyl borane

4-bromo-aniline
106-40-1

4-bromo-aniline

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In tetrahydrofuran Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;82%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With oxalic acid hydrazide; ammonium hydroxide; tetrabutylammomium bromide; potassium carbonate; 2,5-hexanedione; copper(II) oxide In water at 90℃; for 1.33333h;78%
4-nitrostyrene
100-13-0

4-nitrostyrene

A

4-ethylnitrobenzene
100-12-9

4-ethylnitrobenzene

B

4-vinyl benzylamine
1520-21-4

4-vinyl benzylamine

C

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With borane-ammonia complex In ethanol at 20℃; for 0.25h; Reagent/catalyst; Schlenk technique;A 10.86%
B 76.84%
C 12.25%
With 4-methylcyclohexene In methanol at 69.84℃; for 1h; Inert atmosphere;
With platinum doped titanium oxide In toluene at 80℃; under 7500.75 Torr; Autoclave;
ammonium hydroxide
1336-21-6

ammonium hydroxide

1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; potassium phosphate tribasic heptahydrate; water; Sucrose In water at 90℃; for 15h; Catalytic behavior; Green chemistry;75%
p-ethylbenzoic acid
619-64-7

p-ethylbenzoic acid

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
Stage #1: p-ethylbenzoic acid With trifluorormethanesulfonic acid; trimethylsilylazide In chloroform at 90℃; for 0.0666667h; Schmidt Reaction; Flow reactor;
Stage #2: With water In methanol; chloroform at 20℃; Schmidt Reaction; Flow reactor;
69%
4-ethylnitrobenzene
100-12-9

4-ethylnitrobenzene

A

1-(4-aminophenyl)ethanol
93453-80-6, 14572-89-5

1-(4-aminophenyl)ethanol

B

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With 9,10-dihydro-10-methylacridine; perchloric acid In acetonitrile at 59.9℃; for 0.833333h;A 40%
B 60%
methane
34557-54-5

methane

aniline
62-53-3

aniline

A

ortho-ethylaniline
578-54-1

ortho-ethylaniline

B

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
In gaseous matrix at 80℃; Irradiation;A 57%
B 43 % Spectr.
1,4-diethylbenzene
105-05-5

1,4-diethylbenzene

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

Conditions
ConditionsYield
With sodium azide; oxygen; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone at 40℃; for 4h; Sealed tube;53%
3,3-Diazido-2-cyan-acrylsaeure-methylester
82140-87-2

3,3-Diazido-2-cyan-acrylsaeure-methylester

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

A

3-Azido-2-cyan-3-(4-ethylanilino)acrylsaeure-methylester
130148-86-6

3-Azido-2-cyan-3-(4-ethylanilino)acrylsaeure-methylester

B

C8H11N*HN3

C8H11N*HN3

Conditions
ConditionsYield
In dichloromethane at -30℃; for 16h;A 100%
B n/a
diethyl 2-ethoxymethylenemalonate
87-13-8

diethyl 2-ethoxymethylenemalonate

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

2-(((4-ethylphenyl)amino)methylene)diethyl malonate
111186-10-8

2-(((4-ethylphenyl)amino)methylene)diethyl malonate

Conditions
ConditionsYield
at 130℃; for 2h;100%
With toluene-4-sulfonic acid In pentane Reflux;96%
at 120℃; for 3h;
In ethanol at 80℃; for 4h;
chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

2-methoxyethyl isothiocyanate
38663-85-3

2-methoxyethyl isothiocyanate

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

(Z)-2-((4-ethylphenyl)imino)-3-(2-methoxyethyl)thiazolidin-4-one

(Z)-2-((4-ethylphenyl)imino)-3-(2-methoxyethyl)thiazolidin-4-one

Conditions
ConditionsYield
Stage #1: 2-methoxyethyl isothiocyanate; 4-aminoethylbenzene In ethanol at 78℃; for 12h; Knoevenagel Condensation;
Stage #2: chloroacetic acid ethyl ester With sodium acetate In ethanol at 78℃; for 5h; regioselective reaction;
100%
1H-indazole-5-sulfonyl chloride

1H-indazole-5-sulfonyl chloride

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

1H-indazole-5-sulfonic acid (4-ethylphenyl)amide

1H-indazole-5-sulfonic acid (4-ethylphenyl)amide

Conditions
ConditionsYield
With pyridine at 50℃; for 4h;100%
With pyridine at 50℃;98%
2,5-hexanedione
110-13-4

2,5-hexanedione

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

1-(4-ethylphenyl)-2,5-dimethyl-1H-pyrrole

1-(4-ethylphenyl)-2,5-dimethyl-1H-pyrrole

Conditions
ConditionsYield
With montmorillonite K-10 In dichloromethane at 20 - 90℃; for 0.1h; Paal-Knorr Pyrrole Synthesis; Microwave irradiation;99%
With bentonite In neat (no solvent) at 20℃; for 0.05h; Reagent/catalyst; Paal-Knorr Pyrrole Synthesis; Milling; Green chemistry;98%
In neat (no solvent) at 20℃; for 24h; Paal-Knorr Pyrrole Synthesis; Green chemistry;90%
anthranilic acid
118-92-3

anthranilic acid

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

3-(4-ethylphenyl)quinazolin-4(3H)-one
22874-41-5

3-(4-ethylphenyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With ytterbium(III) triflate at 60℃; for 0.0333333h;99%
cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

trans-2-(4-ethylanilino)cyclohexan-1-ol

trans-2-(4-ethylanilino)cyclohexan-1-ol

Conditions
ConditionsYield
With 2CF3O3S(1-)*4CH4O*2C19H13N3O2(2-)*Co(3+)*5H2O*Tb(3+) at 20℃; for 4h; Neat (no solvent); Inert atmosphere;99%
With {Co3+-Zn2+} metal-organic framework at 20℃; for 4h; neat (no solvent);99%
With sulfated zirconia In neat (no solvent) at 20℃; for 1h; regioselective reaction;80%
2-bromobenzoic acid chloride
7154-66-7

2-bromobenzoic acid chloride

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

2-bromo-N-(4-ethylphenyl)benzamide
296273-16-0

2-bromo-N-(4-ethylphenyl)benzamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 3h;99%
With triethylamine In dichloromethane
styrene oxide
96-09-3

styrene oxide

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

C16H19NO
1260096-13-6

C16H19NO

Conditions
ConditionsYield
With 2CF3O3S(1-)*4CH4O*2C19H13N3O2(2-)*Co(3+)*5H2O*Tb(3+) at 20℃; for 4h; Neat (no solvent); Inert atmosphere; regioselective reaction;99%
With {Co3+-Cd2+} metal-organic framework at 20℃; for 4h; neat (no solvent);99%
With 3Zn(2+)*Co(3+)*2C21H11N3O6(4-)*HO(1-)*17H2O In neat (no solvent) at 20℃; for 4h; Reagent/catalyst; regioselective reaction;> 99 %Chromat.
naphthalen-2-yl tosylate
7385-85-5

naphthalen-2-yl tosylate

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

(4-ethyl-phenyl)-[2]naphthyl-amine

(4-ethyl-phenyl)-[2]naphthyl-amine

Conditions
ConditionsYield
With (1,3-bis(2,6-diisopropylphenyl)imidazolidene)Ni(styrene)2; lithium tert-butoxide In 1,4-dioxane for 10h; Inert atmosphere; Heating; Schlenk technique;99%
4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

benzyl alcohol
100-51-6

benzyl alcohol

N-benzyl 4-ethylaniline
109240-32-6

N-benzyl 4-ethylaniline

Conditions
ConditionsYield
With C55H43ClN5P2Ru(1+)*Cl(1-); potassium hydroxide In toluene at 140℃; for 2h; Sealed tube;99%
With 2,2':6,2''-terpyridine In toluene at 160℃; for 1h; Microwave irradiation;96%
With 1,4-diaza-bicyclo[2.2.2]octane; rhodium(III) acetylacetonate; potassium hydroxide In acetonitrile at 110℃; Sealed tube;92%
C7H6F3NO3
1275518-55-2

C7H6F3NO3

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

3-(4,4,4-trifluoro-3-(4-ethylanilino)butanoyl)oxazolidin-2-one

3-(4,4,4-trifluoro-3-(4-ethylanilino)butanoyl)oxazolidin-2-one

Conditions
ConditionsYield
In neat (no solvent) at 20℃; for 3h; Michael Addition;99%
In neat (no solvent) at 20℃; for 3h; Michael Addition;99%
C11H19N3O4S

C11H19N3O4S

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

C19H30N4O4S

C19H30N4O4S

Conditions
ConditionsYield
In dichloromethane; acetonitrile at 50℃; Inert atmosphere;99%
tert-Butoxybis(dimethylamino)methane
5815-08-7

tert-Butoxybis(dimethylamino)methane

ethyl 2-(2-ethoxy-2-oxoethyl)-4,5-dimethoxybenzoate

ethyl 2-(2-ethoxy-2-oxoethyl)-4,5-dimethoxybenzoate

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

2-(4-ethylphenyl)-6,7-dimethoxy-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid

2-(4-ethylphenyl)-6,7-dimethoxy-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: tert-Butoxybis(dimethylamino)methane; ethyl 2-(2-ethoxy-2-oxoethyl)-4,5-dimethoxybenzoate at 100℃; for 3h;
Stage #2: 4-aminoethylbenzene With acetic acid at 20℃; for 2h;
Stage #3: With sodium hydroxide In ethanol at 80℃; for 1h;
99%
Phenyl acetate
122-79-2

Phenyl acetate

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

N-(4-ethylphenyl)acetamide
3663-34-1

N-(4-ethylphenyl)acetamide

Conditions
ConditionsYield
With cell-free extract containing recombinant PpATaseCH In aq. phosphate buffer; dimethyl sulfoxide at 35℃; for 24h; pH=7.5; Time;99%
acetic anhydride
108-24-7

acetic anhydride

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

N-(4-ethylphenyl)acetamide
3663-34-1

N-(4-ethylphenyl)acetamide

Conditions
ConditionsYield
With cadmium(II) oxide at 80℃; for 0.166667h; Neat (no solvent); Microwave irradiation;98%
With ZnAl2O4 nanoparticles at 20℃; for 0.0833333h; Neat (no solvent);96%
In neat (no solvent) at 20℃; for 0.05h;96%
18-crown-6 ether
17455-13-9

18-crown-6 ether

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

4-ethylanilinium tetrafluoroborate-1,4,7,10,13,16-hexaoxacyclooctadecane (1/1)

4-ethylanilinium tetrafluoroborate-1,4,7,10,13,16-hexaoxacyclooctadecane (1/1)

Conditions
ConditionsYield
With tetrafluoroboric acid In methanol at 20℃;98%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

toluene-4-sulfonic acid-(4-ethyl-anilide)
1506-96-3

toluene-4-sulfonic acid-(4-ethyl-anilide)

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 16h;98%
With pyridine In dichloromethane at 20℃; for 3h; Inert atmosphere;
bromobenzene
108-86-1

bromobenzene

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

4-ethyl-N-phenylbenzenamine
32804-22-1

4-ethyl-N-phenylbenzenamine

Conditions
ConditionsYield
With tetrabutylammomium bromide; palladium diacetate; potassium carbonate; 2,6-bis(diphenylphosphino)pyridine In N,N-dimethyl acetamide at 135℃; for 1h; Catalytic behavior; Buchwald-Hartwig Coupling; Inert atmosphere;98%
With potassium ethoxide In 1,4-dioxane at 200℃; Reagent/catalyst; Autoclave;28.6%
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

benzil
134-81-6

benzil

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

1-(4-ethylphenyl)-2-(3-nitrophenyl)-4,5-diphenyl-1H-imidazole

1-(4-ethylphenyl)-2-(3-nitrophenyl)-4,5-diphenyl-1H-imidazole

Conditions
ConditionsYield
With ammonium acetate In neat (no solvent) at 110℃; for 0.666667h; Green chemistry;98%
With ammonium acetate In neat (no solvent) at 80℃; for 0.416667h; Catalytic behavior; Green chemistry;98%
Methyl formate
107-31-3

Methyl formate

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

N-(4-ethylphenyl)formamide
69753-59-9

N-(4-ethylphenyl)formamide

Conditions
ConditionsYield
With calcium(II) bis(trifluoromethanesulfonyl)imide In neat (no solvent) at 115℃; for 1h; Reagent/catalyst; Microwave irradiation; Sealed tube;98%
2,3-pyrazinedicarboxylic anhydride
4744-50-7

2,3-pyrazinedicarboxylic anhydride

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

3-[(4-ethylphenyl)carbamoyl]pyrazine-2-carboxylic acid

3-[(4-ethylphenyl)carbamoyl]pyrazine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 2,3-pyrazinedicarboxylic anhydride; 4-aminoethylbenzene In tetrahydrofuran at 20℃; for 1h;
Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water pH=6;
98%

589-16-2Relevant articles and documents

MOF-Mediated Synthesis of Supported Fe-Doped Pd Nanoparticles under Mild Conditions for Magnetically Recoverable Catalysis**

Darawsheh, Mohanad D.,Mazarío, Jaime,Lopes, Christian W.,Giménez-Marqués, Mónica,Domine, Marcelo E.,Meira, Debora M.,Martínez, Jordan,Mínguez Espallargas, Guillermo,O?a-Burgos, Pascual

, p. 13659 - 13667 (2020)

Metal–organic framework (MOF)-driven synthesis is considered as a promising alternative for the development of new catalytic materials with well-designed active sites. This synthetic approach is used here to gradually transform a new bimetallic MOF, with Pd and Fe as the metal components, by the in situ generation of aniline under mild conditions. This methodology results in a compositionally homogeneous nanocomposite formed by Fe-doped Pd nanoparticles that, in turn, are supported on iron oxide-doped carbon. The nanocomposite has been fully characterized by several techniques such as IR and Raman spectroscopy, TEM, XPS, and XAS. The performance of this nanocomposite as an heterogeneous catalyst for hydrogenation of nitroarenes and nitrobenzene coupling with benzaldehyde has been evaluated, proving it to be an efficient and reusable catalyst.

Rh-PVP Catalyzed Reductive Amination of Phenols by Ammonia or Amines to Cyclohexylamines under Solvent-free Conditions

Chaudhari, Chandan,Nagaoka, Katsutoshi,Nishida, Yoshihide,Rumi, Saeki,Sato, Katsutoshi,Shiraishi, Masaya

supporting information, p. 81 - 84 (2022/01/12)

Colloidal metal nanoparticles were examined for reductive amination of phenol by ammonia under mild reaction conditions. The results showed that Rh-PVP was the most active catalyst for reductive amination reaction. Linear, cyclic, and amino alcohols were used as nucleophiles and converted to primary/secondary/tertiary amines. Using this strategy, the synthesis of an industrially important chemical, N-cyclohexyl- 2-pyrrolidone was explored.

Ambient Hydrogenation and Deuteration of Alkenes Using a Nanostructured Ni-Core–Shell Catalyst

Beller, Matthias,Feng, Lu,Gao, Jie,Jackstell, Ralf,Jagadeesh, Rajenahally V.,Liu, Yuefeng,Ma, Rui

supporting information, p. 18591 - 18598 (2021/06/28)

A general protocol for the selective hydrogenation and deuteration of a variety of alkenes is presented. Key to success for these reactions is the use of a specific nickel-graphitic shell-based core–shell-structured catalyst, which is conveniently prepared by impregnation and subsequent calcination of nickel nitrate on carbon at 450 °C under argon. Applying this nanostructured catalyst, both terminal and internal alkenes, which are of industrial and commercial importance, were selectively hydrogenated and deuterated at ambient conditions (room temperature, using 1 bar hydrogen or 1 bar deuterium), giving access to the corresponding alkanes and deuterium-labeled alkanes in good to excellent yields. The synthetic utility and practicability of this Ni-based hydrogenation protocol is demonstrated by gram-scale reactions as well as efficient catalyst recycling experiments.

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