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  • 1585-07-5 Structure
  • Basic information

    1. Product Name: 4-Bromoethylbenzene
    2. Synonyms: 1-Bromo-4-Ethylbenzene,2PbrC8H7Br;4-Bromethylbenzol;2PBr;4-Bromo-1-ethylbenzene;4-Ethyl-1-bromobenzene;4-Ethylphenyl bromide;p-Bromoethylbenzene,99%;Ethyl broMobenzene
    3. CAS NO:1585-07-5
    4. Molecular Formula: C8H9Br
    5. Molecular Weight: 185.06
    6. EINECS: 216-439-8
    7. Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Halides;Phenyls & Phenyl-Het;Benzene derivates;Bromine Compounds;4-Alkylbromobenzenes (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Phenyls & Phenyl-Het;Aryl;C8;Halogenated Hydrocarbons
    8. Mol File: 1585-07-5.mol
    9. Article Data: 96
  • Chemical Properties

    1. Melting Point: -43°C
    2. Boiling Point: 204 °C(lit.)
    3. Flash Point: 147 °F
    4. Appearance: Clear colourless to light yellow liquid
    5. Density: 1.343 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.405mmHg at 25°C
    7. Refractive Index: n20/D 1.544(lit.)
    8. Storage Temp.: Store below +30°C.
    9. Solubility: Chloroform, Ethyl Acetate, Methanol
    10. Water Solubility: Insoluble in water.
    11. Stability: Stable. Incompatible with strong oxidizing agents.
    12. BRN: 1856989
    13. CAS DataBase Reference: 4-Bromoethylbenzene(CAS DataBase Reference)
    14. NIST Chemistry Reference: 4-Bromoethylbenzene(1585-07-5)
    15. EPA Substance Registry System: 4-Bromoethylbenzene(1585-07-5)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 23-24/25
    4. RIDADR: UN 2810
    5. WGK Germany: 3
    6. RTECS:
    7. TSCA: T
    8. HazardClass: IRRITANT
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 1585-07-5(Hazardous Substances Data)

1585-07-5 Usage

Description

4-Bromoethylbenzene, also known as 1-Bromo-4-ethylbenzene, is an organobromine compound characterized by its clear, colorless to light yellow liquid appearance. It is an important intermediate in various chemical syntheses and possesses flame retardant properties.

Uses

Used in Flame Retardancy:
4-Bromoethylbenzene is used as a flame retardant in the industry due to its organobromine nature, which helps to slow down the spread of fire and improve the safety of materials.
Used in Organic Synthesis:
4-Bromoethylbenzene serves as a crucial raw material and intermediate in organic synthesis, where it is utilized to create a wide range of chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 4-Bromoethylbenzene is employed as an intermediate for the synthesis of various drugs, contributing to the development of new medications.
Used in Agrochemicals:
The compound is also used as an intermediate in the production of agrochemicals, such as pesticides and fertilizers, to enhance agricultural productivity and crop protection.
Used in Dye Industry:
4-Bromoethylbenzene is utilized as an intermediate in the synthesis of dyes, playing a significant role in the textile and coloring industries.
Used in Liquid Crystals:
As an intermediate, 4-Bromoethylbenzene is involved in the production of liquid crystals, which are essential components in the manufacturing of display devices such as televisions, computer monitors, and smartphones.
Chemical Properties:
4-Bromoethylbenzene undergoes oxidation to yield 4′-bromoacetophenone with a 74.3% yield, showcasing its reactivity and versatility in chemical reactions. Its clear, colorless to light yellow liquid appearance indicates its stability and suitability for various applications across different industries.

Synthesis Reference(s)

Tetrahedron Letters, 15, p. 3395, 1974 DOI: 10.1016/S0040-4039(01)91916-1

Check Digit Verification of cas no

The CAS Registry Mumber 1585-07-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,8 and 5 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1585-07:
(6*1)+(5*5)+(4*8)+(3*5)+(2*0)+(1*7)=85
85 % 10 = 5
So 1585-07-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H9Br/c1-7(9)8-5-3-2-4-6-8/h2-7H,1H3

1585-07-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Bromo-4-ethylbenzene

1.2 Other means of identification

Product number -
Other names 1-Bromo-4-Ethylbenzene

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:1585-07-5 SDS

1585-07-5Synthetic route

1-bromo-4-ethenyl-benzene
2039-82-9

1-bromo-4-ethenyl-benzene

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
With C50H57IrN2P; hydrogen In dichloromethane at -78 - 20℃;100%
With hydrogen In methanol; ethanol at 25℃; under 5171.62 Torr; for 18h; Inert atmosphere;99%
With 0.42C23H20N4O4*2Cl(1-)*Zn(2+)*10.16H2O*0.58Pd(2+)*0.58C23H20N4O4(1-); hydrogen In tetrahydrofuran at 20℃; under 760.051 Torr; for 1h;99%
1-bromo-4-ethenyl-benzene
2039-82-9

1-bromo-4-ethenyl-benzene

2-(4-(tert-butyl)phenyl)benzo[d][1,3,2]dioxaborole
241147-96-6

2-(4-(tert-butyl)phenyl)benzo[d][1,3,2]dioxaborole

A

para-tert-butylphenol
98-54-4

para-tert-butylphenol

B

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
With oxygen; hydrazine hydrate In acetonitrile at 32℃; under 760.051 Torr; for 3h; Schlenk technique;A 99%
B 89%
4-bromo-1-ethynylbenzene
766-96-1

4-bromo-1-ethynylbenzene

A

1-bromo-4-ethenyl-benzene
2039-82-9

1-bromo-4-ethenyl-benzene

B

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
With hydrogen In hexane at 40℃; under 760.051 Torr; for 6h;A 97%
B 3%
With hydrogen; dimethyl sulfoxide In ethyl acetate at 20℃; under 760.051 Torr; for 24h;A 88 %Spectr.
B 9 %Spectr.
1-bromo-4-ethenyl-benzene
2039-82-9

1-bromo-4-ethenyl-benzene

A

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

1-bromo-4-ethylbenzene

B

ethylbenzene
100-41-4

ethylbenzene

Conditions
ConditionsYield
With iron(III) chloride; lithium aluminium tetrahydride; hydrogen In tetrahydrofuran at 18℃; under 750.075 Torr; for 6h; Inert atmosphere; Sealed tube;A 94%
B 12%
With palladium 10% on activated carbon; hydrogen In isopropyl alcohol at 50℃; under 4950.5 Torr;
para-bromoacetophenone
99-90-1

para-bromoacetophenone

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
With gallium(III) triflate; dimethylmonochlorosilane In dichloromethane at 20℃; for 1.5h;89%
With lithium aluminium tetrahydride; diphosphorus tetraiodide In benzene for 3h; Heating;87%
With titanium tetrachloride; dimethylamine borane In dichloromethane for 0.5h; Ambient temperature;80%
2-(4-bromophenyl)-2-methyl-1,3-dithiolane
41159-12-0

2-(4-bromophenyl)-2-methyl-1,3-dithiolane

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In tetrahydrofuran; methanol at 20℃; for 0.333333h;86%
ethylbenzene
100-41-4

ethylbenzene

A

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

1-bromo-4-ethylbenzene

B

1-bromo-2-ethylbenzene
1973-22-4

1-bromo-2-ethylbenzene

Conditions
ConditionsYield
With oxygen; sodium bromide In dibutyl ether at 45℃; under 760.051 Torr; for 5h; Schlenk technique;A 83%
B 9%
With carbon dioxide; bromine at 40℃; under 187519 Torr; for 2h; Supercritical conditions; Green chemistry;A 64%
B 36%
With ammonium nitrate; N-Bromosuccinimide In acetonitrile for 8h;A 53%
B 30%
1-(4-bromophenyl)ethanol
5391-88-8

1-(4-bromophenyl)ethanol

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
With indium(III) chloride; diphenylsilyl chloride In dichloromethane at 20℃; for 3h;83%
With formic acid; methanesulfonic acid; 1,2-bis((di-tert-butylphosphoryl)methyl)benzene; palladium(II) acetylacetonate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In 1,2-dichloro-ethane at 100℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere;62 %Chromat.
ethylbenzene
100-41-4

ethylbenzene

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
With sulfuric acid; sodium bromide at 60℃; for 2h;81%
With sulfur dioxide; bromine; nitric acid; acetic acid Lichtausschluss;
(bromination);
With bromine; iodine; iron
methyl (E)-2-(1-(4-bromophenyl)ethylidene)hydrazine-1-carboxylate

methyl (E)-2-(1-(4-bromophenyl)ethylidene)hydrazine-1-carboxylate

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
With potassium hydroxide In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 140℃; for 4h; Wolff-Kishner Reduction;76%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

bis(iodozinc)methane
31729-70-1

bis(iodozinc)methane

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
With Wilkinson's catalyst; hydrogen In tetrahydrofuran at 25℃; under 760.051 Torr;76%
C12H9BrN2O4S2

C12H9BrN2O4S2

triethyl borane
97-94-9

triethyl borane

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
Pd(Cl2)dppf In tetrahydrofuran at 20℃; for 30h;74%
triethyl borane
97-94-9

triethyl borane

4-bromophenyl trifluoromethanesulfonate
66107-30-0

4-bromophenyl trifluoromethanesulfonate

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium acetate In tetrahydrofuran Suzuki-Miyaura cross-coupling; Reflux; Inert atmosphere;72%
ethylbenzene
100-41-4

ethylbenzene

A

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

1-bromo-4-ethylbenzene

B

(1-bromoethyl)benzne
585-71-7, 38661-81-3

(1-bromoethyl)benzne

Conditions
ConditionsYield
With K10-montmorillonite clay; bromine In tetrachloromethane for 1.5h; Ambient temperature;A 69%
B 25%
With 1-butyl-3-methylimidazolium tribromide at 50℃; for 2.5h; regioselective reaction;
1-bromo-4-ethenyl-benzene
2039-82-9

1-bromo-4-ethenyl-benzene

carbon monoxide
201230-82-2

carbon monoxide

A

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

1-bromo-4-ethylbenzene

B

2-(4-bromophenyl)propanal
40460-91-1

2-(4-bromophenyl)propanal

C

3-(4-bromophenyl)propanal
80793-25-5

3-(4-bromophenyl)propanal

Conditions
ConditionsYield
With hydrogen; N-dodecyl-N-(2-hydroxyethyl)-N,N-dimethylammonium bromide; {Rh(cod)[μ-S(CH2)3Si(OMe)3]}2; triphenylphosphine In water; butan-1-ol at 80℃; under 10350.8 Torr; for 6h; microemulsion/sol-gel;A 1.3%
B 51%
C 16.5%
ethylbenzene
100-41-4

ethylbenzene

A

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

1-bromo-4-ethylbenzene

B

para-bromophenacyl bromide
99-73-0

para-bromophenacyl bromide

Conditions
ConditionsYield
With oxone; sodium bromide In water; acetonitrile at 50℃;A 13%
B 16%
ethyl bromide
74-96-4

ethyl bromide

bromobenzene
108-86-1

bromobenzene

A

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

1-bromo-4-ethylbenzene

B

1-bromo-2-ethylbenzene
1973-22-4

1-bromo-2-ethylbenzene

Conditions
ConditionsYield
With aluminium at 80℃;
diethyl sulfate
64-67-5

diethyl sulfate

(4-bromophenyl)magnesium bromide
18620-02-5

(4-bromophenyl)magnesium bromide

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
With diethyl ether; benzene
ethylbenzene
100-41-4

ethylbenzene

A

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

1-bromo-4-ethylbenzene

B

1-ethyl-2,4-dibromo-benzene
66634-86-4

1-ethyl-2,4-dibromo-benzene

Conditions
ConditionsYield
With sulfur dioxide; bromine; nitric acid; acetic acid Lichtausschluss;
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

ethyl iodide
75-03-6

ethyl iodide

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
With sodium; benzene
4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
(i) NaNO2, H2SO4, (ii) CuSO4, Cu, NaBr, aq. H2SO4; Multistep reaction;
bromobenzene
108-86-1

bromobenzene

ethene
74-85-1

ethene

A

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

1-bromo-4-ethylbenzene

B

1-bromo-2-ethylbenzene
1973-22-4

1-bromo-2-ethylbenzene

C

1-bromo-3-ethylbenzene
2725-82-8

1-bromo-3-ethylbenzene

Conditions
ConditionsYield
H-ZSM-5 catalyst at 400℃; Product distribution; alkylation of benzene and momosubstituted benzenes with ethylene over H-ZSM-5 and mordenite-H catalysts; isomerization of ethylarenes over H-mordenite;
1-bromo-4-ethenyl-benzene
2039-82-9

1-bromo-4-ethenyl-benzene

carbon monoxide
201230-82-2

carbon monoxide

A

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

1-bromo-4-ethylbenzene

B

3-(4-bromophenyl)propanal
80793-25-5

3-(4-bromophenyl)propanal

C

(S)-2-(4-bromophenyl)propanal

(S)-2-(4-bromophenyl)propanal

D

(R)-2-(4-bromophenyl)propanal

(R)-2-(4-bromophenyl)propanal

Conditions
ConditionsYield
With hydrogen; tin(ll) chloride; ((2S,4S)-N-(tert-butoxycarbonyl)-4-(diphenylphosphino)-2-{(diphenylphosphino)methyl}pyrrolidine)PtCl2 In benzene at 60℃; under 137044 Torr; for 8h; Yield given. Yields of byproduct given;
ethylbenzene
100-41-4

ethylbenzene

A

bromobenzene
108-86-1

bromobenzene

B

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

1-bromo-4-ethylbenzene

C

1-bromo-2-ethylbenzene
1973-22-4

1-bromo-2-ethylbenzene

Conditions
ConditionsYield
With hydrogen bromide; dihydrogen peroxide at 50℃; Product distribution; Kinetics; Thermodynamic data; oth. temperature, var. stirring rate, var. ratio of reactants, E(activ.), ΔH(activ.), ΔS(activ.), ΔG(activ.);A 1.6 % Chromat.
B 73.3 % Chromat.
C 22.2 % Chromat.
With hydrogenchloride; sodium hypochlorite; sodium bromide In water at 19.85℃; for 5h; Product distribution; Further Variations:; Temperatures;
ethylbenzene
100-41-4

ethylbenzene

A

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

1-bromo-4-ethylbenzene

B

1-bromo-2-ethylbenzene
1973-22-4

1-bromo-2-ethylbenzene

C

1-bromo-3-ethylbenzene
2725-82-8

1-bromo-3-ethylbenzene

Conditions
ConditionsYield
With bromine; iron(III) chloride In acetic acid at 25 - 75℃; Rate constant; Product distribution; other solvents (nitromethane, acetic anhydride), k (rel. to benzene);
1-bromo-2-ethylbenzene
1973-22-4

1-bromo-2-ethylbenzene

A

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

1-bromo-4-ethylbenzene

B

1-bromo-3-ethylbenzene
2725-82-8

1-bromo-3-ethylbenzene

Conditions
ConditionsYield
H-mordenite at 250℃; Product distribution; alkylation of benzene and momosubstituted benzenes with ethylene over H-ZSM-5 and mordenite-H catalysts; isomerization of ethylarenes over H-mordenite;
styrene
292638-84-7

styrene

para-bromoacetophenone
99-90-1

para-bromoacetophenone

A

1-bromo-4-ethenyl-benzene
2039-82-9

1-bromo-4-ethenyl-benzene

B

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

1-bromo-4-ethylbenzene

1-Bromo-4-((1R,2R)-1-methyl-2-phenyl-cyclopropyl)-benzene

1-Bromo-4-((1R,2R)-1-methyl-2-phenyl-cyclopropyl)-benzene

C16H14Br2

C16H14Br2

Conditions
ConditionsYield
In ethanol Mechanism; Zn(Hg), HCl;
With amalgamated zinc In ethanol at 20℃;
para-bromoacetophenone
99-90-1

para-bromoacetophenone

A

1-bromo-4-ethenyl-benzene
2039-82-9

1-bromo-4-ethenyl-benzene

B

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

1-bromo-4-ethylbenzene

1-Bromo-4-((1R,2R)-1-methyl-2-phenyl-cyclopropyl)-benzene

1-Bromo-4-((1R,2R)-1-methyl-2-phenyl-cyclopropyl)-benzene

C16H14Br2

C16H14Br2

Conditions
ConditionsYield
With styrene; amalgamated zinc In ethanol at 20℃;
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

ethyl iodide
75-03-6

ethyl iodide

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

1-bromo-4-ethylbenzene

Conditions
ConditionsYield
With CuI*P(Et)3; naphthalen-1-yl-lithium 1.) THF, 25 deg C, 30 min, 2.) 25 deg C, 30 min; Yield given. Multistep reaction;
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

1-bromo-4-(1-bromoethyl)benzene
159755-11-0

1-bromo-4-(1-bromoethyl)benzene

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 90℃; for 3h;100%
With bromine In tetrachloromethane at 50℃; for 1.25h; Irradiation;98%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 90℃; for 3h;68%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

phenylboronic acid
98-80-6

phenylboronic acid

4-ethylbiphenyl
5707-44-8

4-ethylbiphenyl

Conditions
ConditionsYield
With potassium tert-butylate In ethanol; water at 25℃; for 17h; Suzuki-Miyaura Coupling;98%
With sodium carbonate; palladium on activated charcoal In ethanol at 80℃; for 19h;96%
With potassium carbonate In water at 75℃; for 5h; Suzuki-Miyaura coupling; Inert atmosphere;94%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

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

1-bromo-4-ethylbenzene

(4-ethylphenyl)trimethylsilane
17988-50-0

(4-ethylphenyl)trimethylsilane

Conditions
ConditionsYield
Stage #1: 1-bromo-4-ethylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃;
98%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

4-(4-ethylphenyl)-2-methylbut-3-yn-2-ol
155105-68-3

4-(4-ethylphenyl)-2-methylbut-3-yn-2-ol

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 60℃; for 24h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;98%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

para-bromoacetophenone
99-90-1

para-bromoacetophenone

Conditions
ConditionsYield
With tert.-butylhydroperoxide In water at 20℃; for 18h; Sealed tube;97%
With Iron(III) nitrate nonahydrate; 1-hydroxy-pyrrolidine-2,5-dione; oxygen In benzonitrile at 90℃; for 30h;97%
With Oxone; potassium bromide In nitromethane at 50℃; for 24h;96%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

4,4'-diethylbiphenyl
13049-40-6

4,4'-diethylbiphenyl

Conditions
ConditionsYield
With caesium carbonate In water at 80℃; for 24h; Ullmann Condensation; Green chemistry;97%
With 2Pd(2+)*4Br(1-)*C56H102N4; potassium carbonate at 75℃; for 12h; Ullmann Condensation;92%
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / 3 h / -78 °C
1.2: -78 - 20 °C
1.3: 1 h
2.1: caesium carbonate / 1-methyl-pyrrolidin-2-one; water / 20 h / 120 °C
View Scheme
With potassium carbonate; benzyl alcohol In acetonitrile at 30℃; for 10h; Ullmann Condensation; Inert atmosphere; Irradiation;99 %Chromat.
phthalimide
136918-14-4

phthalimide

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

1-bromo-4-ethylbenzene

3-(4-ethylphenyl)-3-hydroxyisoindolin-1-one
1436866-94-2

3-(4-ethylphenyl)-3-hydroxyisoindolin-1-one

Conditions
ConditionsYield
Stage #1: 1-bromo-4-ethylbenzene With magnesium In tetrahydrofuran
Stage #2: phthalimide In tetrahydrofuran; dichloromethane at 20℃; for 1.5h; Inert atmosphere;
96%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

(2-(4-ethylphenyl)ethynyl)trimethylsilane

(2-(4-ethylphenyl)ethynyl)trimethylsilane

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 120℃; for 0.0833333h; Sonogashira Cross-Coupling; Microwave irradiation; Sealed tube; Inert atmosphere;95%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In N,N-dimethyl-formamide at 120℃; for 0.5h; microwave-assisted Sonogashira reaction; Microwave irradiation;85%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4-ethyl-4'-methoxy-1,1'-biphenyl
58244-47-6

4-ethyl-4'-methoxy-1,1'-biphenyl

Conditions
ConditionsYield
With potassium phosphate tribasic heptahydrate; C31H25N2O4PPd In toluene at 80℃; for 2h;93.5%
aqueous NH4 Cl

aqueous NH4 Cl

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

1-bromo-4-ethylbenzene

(4-ethylphenyl)trimethylsilane
17988-50-0

(4-ethylphenyl)trimethylsilane

Conditions
ConditionsYield
With chloro-trimethyl-silane; magnesium In tetrahydrofuran93%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

p-bromobenzamide
698-67-9

p-bromobenzamide

Conditions
ConditionsYield
With tert.-butylhydroperoxide; ammonia; iodine In water at 100℃; for 3h; Sealed tube; Green chemistry;93%
Stage #1: 1-bromo-4-ethylbenzene With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); water In ethyl acetate at 60℃; for 6h;
Stage #2: With ammonium hydroxide; iodine In ethyl acetate; acetonitrile at 20℃; for 12h;
83%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

carbon monoxide
201230-82-2

carbon monoxide

acetylacetone
123-54-6

acetylacetone

1-(4-ethylphenyl)butane-1,3-dione
58278-92-5

1-(4-ethylphenyl)butane-1,3-dione

Conditions
ConditionsYield
With dichloro(1,5-cyclooctadiene)palladium(II); triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; magnesium chloride In 1,4-dioxane at 80℃; for 18h; Sealed tube;93%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

4-ethylbenzylaldehyde
4748-78-1

4-ethylbenzylaldehyde

Conditions
ConditionsYield
With samarium; copper(l) iodide at 20℃; for 4h; Inert atmosphere;93%
10-Undecenal
112-45-8

10-Undecenal

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

1-bromo-4-ethylbenzene

1-Ethyl-4-undec-10-enyl-benzene
90900-80-4

1-Ethyl-4-undec-10-enyl-benzene

Conditions
ConditionsYield
With ammonia; lithium In diethyl ether Ambient temperature;92%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

4-bromo-α-(p-toluenesulfonylamido)ethylbenzene

4-bromo-α-(p-toluenesulfonylamido)ethylbenzene

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; iodine at 50℃; Inert atmosphere;92%
With N-iodo-succinimide In dichloromethane at 20℃; for 16h; Irradiation;74%
With tetrabutylammonium tetrafluoroborate In 1,2-dichloro-ethane at 20℃; for 2.5h; Electrochemical reaction; Inert atmosphere; regioselective reaction;74%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

1,2,4,5-tetrahydro-3-methyl-3H-3-benzazepin-2-one
73644-95-8

1,2,4,5-tetrahydro-3-methyl-3H-3-benzazepin-2-one

1-(4-ethylphenyl)-4,5-dihydro-3-methyl-1H-benzo[d]azepin-2(3H)-one
1428449-40-4

1-(4-ethylphenyl)-4,5-dihydro-3-methyl-1H-benzo[d]azepin-2(3H)-one

Conditions
ConditionsYield
With copper(l) iodide; palladium diacetate; sodium hydride; triphenylphosphine In 1,4-dioxane; N,N-dimethyl-formamide at 100℃; for 0.166667h; Microwave irradiation;92%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

2-trimethylsilyl ethane sulfonic acid azide
871949-46-1

2-trimethylsilyl ethane sulfonic acid azide

C13H22BrNO2SSi

C13H22BrNO2SSi

Conditions
ConditionsYield
Stage #1: 1-bromo-4-ethylbenzene; 2-trimethylsilyl ethane sulfonic acid azide at -10℃; for 0.5h; Inert atmosphere; Molecular sieve;
Stage #2: With C61H44F4N2O3Ru at -10℃; for 24h; Inert atmosphere; Molecular sieve;
92%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

benzyl(bromo)zinc
62673-31-8

benzyl(bromo)zinc

1-benzyl-4-ethylbenzene
620-85-9

1-benzyl-4-ethylbenzene

Conditions
ConditionsYield
With SiliaCat DPP-Pd In tetrahydrofuran at 60℃; for 0.1h; Negishi Coupling; Inert atmosphere; Flow reactor;92%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

1-ethyl-4-(4-methylphenyl)benzene
76708-90-2

1-ethyl-4-(4-methylphenyl)benzene

Conditions
ConditionsYield
With potassium carbonate In water; dimethyl sulfoxide at 60℃; for 24h; Suzuki-Miyaura coupling;91%
With potassium carbonate In ethanol; water at 50℃; for 2h; Catalytic behavior; Suzuki-Miyaura Coupling;89%
With water; triethylamine; Pd(OAc)2EnCatTM In N,N-dimethyl-formamide at 120℃; for 0.25h; Suzuki-Miyaura reaction; microwave irradiation;72%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

5-bromo-4-(bromomethyl)-2-chloro-N-methoxy-N-methylbenzamide

5-bromo-4-(bromomethyl)-2-chloro-N-methoxy-N-methylbenzamide

[5-bromo-4-(bromomethyl)-2-chlorophenyl](4-ethylphenyl)methanone

[5-bromo-4-(bromomethyl)-2-chlorophenyl](4-ethylphenyl)methanone

Conditions
ConditionsYield
Stage #1: 1-bromo-4-ethylbenzene With magnesium In tetrahydrofuran; ethylene dibromide at 20 - 48℃; Large scale;
Stage #2: 5-bromo-4-(bromomethyl)-2-chloro-N-methoxy-N-methylbenzamide In tetrahydrofuran; ethylene dibromide at 25℃; for 2h; Inert atmosphere; Large scale;
91%
bis(tetrahydrofuran)tris(trimethylsilylmethyl)yttrium(III)

bis(tetrahydrofuran)tris(trimethylsilylmethyl)yttrium(III)

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

1-bromo-4-ethylbenzene

4-(trimethylsilylmethyl)ethylbenzene

4-(trimethylsilylmethyl)ethylbenzene

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); XPhos In toluene at 20℃; for 1h; Inert atmosphere; Schlenk technique;91%
3,7-dimethyl-oct-6-enal
106-23-0, 26489-02-1

3,7-dimethyl-oct-6-enal

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

1-bromo-4-ethylbenzene

1-(3,7-Dimethyl-oct-6-enyl)-4-ethyl-benzene
93741-47-0

1-(3,7-Dimethyl-oct-6-enyl)-4-ethyl-benzene

Conditions
ConditionsYield
With ammonia; lithium In diethyl ether90%
3,7-dimethyl-2,6-octadienal
141-27-5

3,7-dimethyl-2,6-octadienal

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

1-bromo-4-ethylbenzene

1-((E)-3,7-Dimethyl-octa-2,6-dienyl)-4-ethyl-benzene
93741-43-6

1-((E)-3,7-Dimethyl-octa-2,6-dienyl)-4-ethyl-benzene

Conditions
ConditionsYield
With ammonia; lithium In diethyl ether for 1h;90%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(4-ethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1075719-87-7

2-(4-ethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane at -60℃;90%
With n-butyllithium In tetrahydrofuran; hexane at -60℃; Flow reactor;87%
1-bromo-4-ethylbenzene
1585-07-5

1-bromo-4-ethylbenzene

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

(E)-methyl 3-(4-ethylphenyl)acrylate

(E)-methyl 3-(4-ethylphenyl)acrylate

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 18h; Heck Reaction; Inert atmosphere;90%

1585-07-5Relevant articles and documents

A uniform bimetallic rhodium/iron nanoparticle catalyst for the hydrogenation of olefins and nitroarenes

Nakamula, Ikuse,Yamanoi, Yoshinori,Imaoka, Takane,Yamamoto, Kimihisa,Nishihara, Hiroshi

, p. 5830 - 5833 (2011)

Mix and more than match: Relative to the catalytic activity of pure Rh nanoparticles in a dendrimer cage, Rh/Fe bimetallic nanoparticles in dendrimers have improved catalytic activity towards the hydrogenation of olefins, and unlike Wilkinson catalyst could catalyze nitroarene hydrogenation (see scheme, G4=4th generation dendrimer).

Chemoselective Hydrogenation of Olefins Using a Nanostructured Nickel Catalyst

Klarner, Mara,Bieger, Sandra,Drechsler, Markus,Kempe, Rhett

supporting information, p. 2157 - 2161 (2021/05/21)

The selective hydrogenation of functionalized olefins is of great importance in the chemical and pharmaceutical industry. Here, we report on a nanostructured nickel catalyst that enables the selective hydrogenation of purely aliphatic and functionalized olefins under mild conditions. The earth-abundant metal catalyst allows the selective hydrogenation of sterically protected olefins and further tolerates functional groups such as carbonyls, esters, ethers and nitriles. The characterization of our catalyst revealed the formation of surface oxidized metallic nickel nanoparticles stabilized by a N-doped carbon layer on the active carbon support.

Metal-Organic Framework-Confined Single-Site Base-Metal Catalyst for Chemoselective Hydrodeoxygenation of Carbonyls and Alcohols

Antil, Neha,Kumar, Ajay,Akhtar, Naved,Newar, Rajashree,Begum, Wahida,Manna, Kuntal

supporting information, p. 9029 - 9039 (2021/06/28)

Chemoselective deoxygenation of carbonyls and alcohols using hydrogen by heterogeneous base-metal catalysts is crucial for the sustainable production of fine chemicals and biofuels. We report an aluminum metal-organic framework (DUT-5) node support cobalt(II) hydride, which is a highly chemoselective and recyclable heterogeneous catalyst for deoxygenation of a range of aromatic and aliphatic ketones, aldehydes, and primary and secondary alcohols, including biomass-derived substrates under 1 bar H2. The single-site cobalt catalyst (DUT-5-CoH) was easily prepared by postsynthetic metalation of the secondary building units (SBUs) of DUT-5 with CoCl2 followed by the reaction of NaEt3BH. X-ray photoelectron spectroscopy and X-ray absorption near-edge spectroscopy (XANES) indicated the presence of CoII and AlIII centers in DUT-5-CoH and DUT-5-Co after catalysis. The coordination environment of the cobalt center of DUT-5-Co before and after catalysis was established by extended X-ray fine structure spectroscopy (EXAFS) and density functional theory. The kinetic and computational data suggest reversible carbonyl coordination to cobalt preceding the turnover-limiting step, which involves 1,2-insertion of the coordinated carbonyl into the cobalt-hydride bond. The unique coordination environment of the cobalt ion ligated by oxo-nodes within the porous framework and the rate independency on the pressure of H2 allow the deoxygenation reactions chemoselectively under ambient hydrogen pressure.

Palladium Nanocatalysts Encapsulated on Porous Silica @ Magnetic Carbon-Coated Cobalt Nanoparticles for Sustainable Hydrogenation of Nitroarenes, Alkenes and Alkynes.

Purohit, Gunjan,Rawat, Diwan S.,Reiser, Oliver

, p. 569 - 575 (2019/11/19)

Palladium nanoparticles were impregnated on porous silica shell carbon-coated cobalt nanoparticles, resulting in a magnetically retrievable material that was evaluated in the catalytic hydrogenation of nitroarenes, alkenes and alkynes. The prepared material was characterized by HR-XRD, HR-TEM, elemental mapping EDX, ICP-OES and XPS analyses, revealing highly dispersed palladium nanoparticles within the porous platform that could account for the high activity observed. Mild reaction conditions, easy retrievability of the catalyst with the aid of an external magnet, recycling in four runs with a total leaching of 19 ppm (1.2 % of the initially employed Pd amount), and high stability makes this material attractive for sustainable and environmentally benign applications.

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