Conditions | Yield |
---|---|
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
2-(4-(tert-butyl)phenyl)benzo[d][1,3,2]dioxaborole
A
para-tert-butylphenol
B
1-bromo-4-ethylbenzene
Conditions | Yield |
---|---|
With oxygen; hydrazine hydrate In acetonitrile at 32℃; under 760.051 Torr; for 3h; Schlenk technique; | A 99% B 89% |
4-bromo-1-ethynylbenzene
A
1-bromo-4-ethenyl-benzene
B
1-bromo-4-ethylbenzene
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
1-bromo-4-ethylbenzene
Conditions | Yield |
---|---|
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In tetrahydrofuran; methanol at 20℃; for 0.333333h; | 86% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
With sulfuric acid; sodium bromide at 60℃; for 2h; | 81% |
With sulfur dioxide; bromine; nitric acid; acetic acid Lichtausschluss; | |
(bromination); | |
With bromine; iodine; iron |
1-bromo-4-ethylbenzene
Conditions | Yield |
---|---|
With potassium hydroxide In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 140℃; for 4h; Wolff-Kishner Reduction; | 76% |
Conditions | Yield |
---|---|
With Wilkinson's catalyst; hydrogen In tetrahydrofuran at 25℃; under 760.051 Torr; | 76% |
Conditions | Yield |
---|---|
Pd(Cl2)dppf In tetrahydrofuran at 20℃; for 30h; | 74% |
triethyl borane
4-bromophenyl trifluoromethanesulfonate
1-bromo-4-ethylbenzene
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium acetate In tetrahydrofuran Suzuki-Miyaura cross-coupling; Reflux; Inert atmosphere; | 72% |
ethylbenzene
A
1-bromo-4-ethylbenzene
B
(1-bromoethyl)benzne
Conditions | Yield |
---|---|
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
carbon monoxide
A
1-bromo-4-ethylbenzene
B
2-(4-bromophenyl)propanal
C
3-(4-bromophenyl)propanal
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With oxone; sodium bromide In water; acetonitrile at 50℃; | A 13% B 16% |
ethyl bromide
bromobenzene
A
1-bromo-4-ethylbenzene
B
1-bromo-2-ethylbenzene
Conditions | Yield |
---|---|
With aluminium at 80℃; |
diethyl sulfate
(4-bromophenyl)magnesium bromide
1-bromo-4-ethylbenzene
Conditions | Yield |
---|---|
With diethyl ether; benzene |
Conditions | Yield |
---|---|
With sulfur dioxide; bromine; nitric acid; acetic acid Lichtausschluss; |
Conditions | Yield |
---|---|
With sodium; benzene |
Conditions | Yield |
---|---|
(i) NaNO2, H2SO4, (ii) CuSO4, Cu, NaBr, aq. H2SO4; Multistep reaction; |
bromobenzene
ethene
A
1-bromo-4-ethylbenzene
B
1-bromo-2-ethylbenzene
C
1-bromo-3-ethylbenzene
Conditions | Yield |
---|---|
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
carbon monoxide
A
1-bromo-4-ethylbenzene
B
3-(4-bromophenyl)propanal
Conditions | Yield |
---|---|
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
A
bromobenzene
B
1-bromo-4-ethylbenzene
C
1-bromo-2-ethylbenzene
Conditions | Yield |
---|---|
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
A
1-bromo-4-ethylbenzene
B
1-bromo-2-ethylbenzene
C
1-bromo-3-ethylbenzene
Conditions | Yield |
---|---|
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
A
1-bromo-4-ethylbenzene
B
1-bromo-3-ethylbenzene
Conditions | Yield |
---|---|
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
para-bromoacetophenone
A
1-bromo-4-ethenyl-benzene
B
1-bromo-4-ethylbenzene
Conditions | Yield |
---|---|
In ethanol Mechanism; Zn(Hg), HCl; | |
With amalgamated zinc In ethanol at 20℃; |
para-bromoacetophenone
A
1-bromo-4-ethenyl-benzene
B
1-bromo-4-ethylbenzene
Conditions | Yield |
---|---|
With styrene; amalgamated zinc In ethanol at 20℃; |
Conditions | Yield |
---|---|
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
1-bromo-4-(1-bromoethyl)benzene
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
1-bromo-4-ethylbenzene
(4-ethylphenyl)trimethylsilane
Conditions | Yield |
---|---|
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
2-methyl-but-3-yn-2-ol
4-(4-ethylphenyl)-2-methylbut-3-yn-2-ol
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 60℃; for 24h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
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
4,4'-diethylbiphenyl
Conditions | Yield |
---|---|
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
1-bromo-4-ethylbenzene
3-(4-ethylphenyl)-3-hydroxyisoindolin-1-one
Conditions | Yield |
---|---|
Stage #1: 1-bromo-4-ethylbenzene With magnesium In tetrahydrofuran Stage #2: phthalimide In tetrahydrofuran; dichloromethane at 20℃; for 1.5h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
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
4-methoxyphenylboronic acid
4-ethyl-4'-methoxy-1,1'-biphenyl
Conditions | Yield |
---|---|
With potassium phosphate tribasic heptahydrate; C31H25N2O4PPd In toluene at 80℃; for 2h; | 93.5% |
1-bromo-4-ethylbenzene
(4-ethylphenyl)trimethylsilane
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; magnesium In tetrahydrofuran | 93% |
Conditions | Yield |
---|---|
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
carbon monoxide
acetylacetone
1-(4-ethylphenyl)butane-1,3-dione
Conditions | Yield |
---|---|
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
N,N-dimethyl-formamide
4-ethylbenzylaldehyde
Conditions | Yield |
---|---|
With samarium; copper(l) iodide at 20℃; for 4h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With ammonia; lithium In diethyl ether Ambient temperature; | 92% |
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
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
2-trimethylsilyl ethane sulfonic acid azide
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With SiliaCat DPP-Pd In tetrahydrofuran at 60℃; for 0.1h; Negishi Coupling; Inert atmosphere; Flow reactor; | 92% |
1-bromo-4-ethylbenzene
4-methylphenylboronic acid
1-ethyl-4-(4-methylphenyl)benzene
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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% |
1-bromo-4-ethylbenzene
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); XPhos In toluene at 20℃; for 1h; Inert atmosphere; Schlenk technique; | 91% |
3,7-dimethyl-oct-6-enal
1-bromo-4-ethylbenzene
1-(3,7-Dimethyl-oct-6-enyl)-4-ethyl-benzene
Conditions | Yield |
---|---|
With ammonia; lithium In diethyl ether | 90% |
3,7-dimethyl-2,6-octadienal
1-bromo-4-ethylbenzene
1-((E)-3,7-Dimethyl-octa-2,6-dienyl)-4-ethyl-benzene
Conditions | Yield |
---|---|
With ammonia; lithium In diethyl ether for 1h; | 90% |
1-bromo-4-ethylbenzene
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
2-(4-ethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
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
acrylic acid methyl ester
Conditions | Yield |
---|---|
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 18h; Heck Reaction; Inert atmosphere; | 90% |
IUPAC Name: 1-Bromo-4-ethylbenzene
Canonical SMILES: CCC1=CC=C(C=C1)Br
InChI: InChI=1S/C8H9Br/c1-2-7-3-5-8(9)6-4-7/h3-6H,2H2,1H3
InChIKey: URFPRAHGGBYNPW-UHFFFAOYSA-N
Molecular Weight: 185.06106 [g/mol]
Molecular Formula: C8H9Br
XLogP3: 3.6
H-Bond Donor: 0
H-Bond Acceptor: 0
EINECS: 216-439-8
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
Stability: Stable. Incompatible with strong oxidizing agents.
Index of Refraction: 1.54
Molar Refractivity: 43.49 cm3
Molar Volume: 138.4 cm3
Surface Tension: 34 dyne/cm
Density: 1.336 g/cm3
Flash Point: 71.2 °C
Enthalpy of Vaporization: 42.29 kJ/mol
Boiling Point: 204.6 °C at 760 mmHg
Vapour Pressure: 0.373 mmHg at 25 °C
Water Solubility: 23.3 mg/L at 25 °C
Appearance: Clear colourless to light yellow liquid
Melting Point of p-Bromoethylbenzene (CAS NO.1585-07-5): -43 °C
p-Bromoethylbenzene (CAS NO.1585-07-5) is used as an organic reagent and a pharmaceutical intermediate.
Safety Information of p-Bromoethylbenzene (CAS NO.1585-07-5):
Hazard Codes:Xi
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:23-24/25
23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
24/25:Avoid contact with skin and eyes
RIDADR:UN 2810
WGK Germany:3
Hazard Note:Irritant
TSCA:T
HS Code:29036990
p-Bromoethylbenzene (CAS NO.1585-07-5), its Synonyms are 1-Bromo-4-ethylbenzene ; 4-Ethylbromobenzene ; p-Ethylbromobenzene ; Benzene, 1-bromo-4-ethyl- .
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