Conditions | Yield |
---|---|
With methanol; palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Schlenk technique; Inert atmosphere; | 99% |
With methanol; palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Sealed tube; Inert atmosphere; chemoselective reaction; | 70% |
With hydrogen In ethanol at 80℃; under 15001.5 Torr; Flow reactor; Green chemistry; chemoselective reaction; | 18% |
With platinum; benzene Hydrogenation; | |
With sodium acetate trihydrate; toluene-4-sulfonic acid hydrazide In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; |
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% |
ethyl bromide
bromobenzene
A
1-bromo-4-ethylbenzene
B
1-bromo-2-ethylbenzene
Conditions | Yield |
---|---|
With aluminium at 80℃; |
Conditions | Yield |
---|---|
With hydrogen bromide; copper(I) bromide; sodium nitrite | |
With hydrogen bromide; copper; sodium nitrite | |
(i) aq. HBr, NaNO2, (ii) Cu; Multistep reaction; | |
(i) NaNO2, aq. HBr, (ii) Cu; Multistep reaction; | |
(i) (diazotization), aq. HBr, (ii) Cu; 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-ethylbenzene
A
1-bromo-2-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; |
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-(2-iodoethyl)benzene
A
1-bromo-2-(2-bromoethyl)benzene
B
ethylbenzene
C
1-bromo-2-ethylbenzene
D
2-phenethyl iodide
E
2-bromostyrene
F
1-phenyl-2-bromoethane
Conditions | Yield |
---|---|
With methanol; tert.-butyl lithium In tetrahydrofuran at -98℃; Product distribution; Mechanism; |
1-bromo-2-ethylbenzene
Conditions | Yield |
---|---|
With potassium fluoride In N,N-dimethyl-formamide at 50℃; for 3h; Yield given; |
Conditions | Yield |
---|---|
With aluminium trichloride In tetrachloromethane; nitromethane |
ethyl bromide
bromobenzene
A
1-bromo-4-ethylbenzene
B
1-bromo-2-ethylbenzene
ethylbenzene
bromine
A
1-bromo-4-ethylbenzene
B
1-bromo-2-ethylbenzene
ethylbenzene
bromine
iodine
A
1-bromo-4-ethylbenzene
B
1-bromo-2-ethylbenzene
2-Ethyl-1,4-bis-trimethylsilanyl-benzene
1-bromo-2-ethylbenzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Br2 2: KF / dimethylformamide / 3 h / 50 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Fe, Br2 / CCl4 2: AlCl3 / CCl4; nitromethane View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 - 25 °C / Inert atmosphere 2: toluene-4-sulfonic acid hydrazide; sodium acetate trihydrate / tetrahydrofuran / 12 h / 80 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
With [Ir(6-Neo)(COD)Cl] In ethanol under 3750.38 Torr; for 1h; | 69 %Spectr. |
carbon monoxide
2-bromostyrene
A
1-bromo-2-ethylbenzene
D
3-(o-bromophenyl)propanal
Conditions | Yield |
---|---|
With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride In toluene at 40℃; under 30003 Torr; for 128h; Autoclave; Schlenk technique; enantioselective reaction; | A n/a B n/a C n/a D n/a |
With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride In toluene at 100℃; under 30003 Torr; for 24h; Temperature; Autoclave; Schlenk technique; enantioselective reaction; | A n/a B n/a C n/a D n/a |
Conditions | Yield |
---|---|
With palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate In toluene at 100℃; for 12h; | 99% |
With bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate; palladium dichloride In toluene at 80℃; for 18h; | 97% |
With palladium diacetate; sodium t-butanolate; tri-t-butylphosphonium tetraphenylborate complex In toluene at 110℃; for 3h; Inert atmosphere; | 30 g |
With palladium diacetate; sodium t-butanolate; tri-t-butylphosphonium tetraphenylborate complex In toluene at 110℃; for 3h; Inert atmosphere; | 30 g |
1-bromo-2-ethylbenzene
N,N-dimethyl-formamide
2-ethylbenzaldehyde
Conditions | Yield |
---|---|
Stage #1: 1-bromo-2-ethylbenzene In dichloromethane; cyclohexane at -78 - -75℃; for 1.5h; Stage #2: N,N-dimethyl-formamide In dichloromethane; cyclohexane for 1h; Solvent; | 99% |
Stage #1: 1-bromo-2-ethylbenzene With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 3h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexanes at -78℃; for 3h; | 96% |
Stage #1: 1-bromo-2-ethylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; for 0.5h; | 85% |
Stage #1: 1-bromo-2-ethylbenzene With n-butyllithium Stage #2: N,N-dimethyl-formamide Further stages.; | |
Stage #1: 1-bromo-2-ethylbenzene With magnesium In tetrahydrofuran for 2h; Heating / reflux; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 0.5h; Stage #3: With hydrogenchloride; water In tetrahydrofuran |
Conditions | Yield |
---|---|
With Iron(III) nitrate nonahydrate; 1-hydroxy-pyrrolidine-2,5-dione; oxygen In benzonitrile at 90℃; for 21h; | 99% |
With Iron(III) nitrate nonahydrate; N-hydroxyphthalimide In benzonitrile at 100℃; for 20h; | 95% |
With tert.-butylhydroperoxide In acetonitrile at 25 - 35℃; for 20h; Sealed tube; Irradiation; | 75% |
1-bromo-2-ethylbenzene
1-(tert-butoxycarbonyl)-4-aminopiperidine
1-tert-butoxycarbonyl-4-[(2-ethylphenyl)amino]piperidine
Conditions | Yield |
---|---|
With sodium t-butanolate; DavePhos; tris-(dibenzylideneacetone)dipalladium(0) In xylene at 130℃; for 24h; | 98% |
Conditions | Yield |
---|---|
With wild type cytochrome P450 CYP102A1(P450Bm3); oxygen; NADPH Reagent/catalyst; Enzymatic reaction; | 98% |
With Mn(II)T(p-Cl)PP; oxygen In neat (no solvent) at 140℃; under 13501.4 Torr; for 6h; Sealed tube; | 10.5% |
Multi-step reaction with 2 steps 1: sodium anthraquinonesulfonate; air / water; acetonitrile / 18 h / 20 °C / Irradiation 2: sodium tetrahydroborate; methanol / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: dihydroxy-methyl-borane; lithium carbonate; N-fluorobis(benzenesulfon)imide; bathophenanthroline; copper (I) acetate / chlorobenzene / 16 h / 55 °C / Glovebox; Inert atmosphere 2: 1,1,1,3',3',3'-hexafluoro-propanol; water / chlorobenzene; dichloromethane / 16 h / 20 °C / Sealed tube View Scheme |
n-butyllithium
1-bromo-2-ethylbenzene
2-(n-butyl)ethylbenzene
Conditions | Yield |
---|---|
With bis(tri-t-butylphosphine)palladium(0); water; sodium chloride In cyclohexane at 20℃; for 0.00555556h; pH=6; Schlenk technique; | 98% |
Conditions | Yield |
---|---|
With bis(tri-t-butylphosphine)palladium(0); water; sodium chloride In cyclohexane at 20℃; for 0.00555556h; pH=6; Schlenk technique; | 98% |
Conditions | Yield |
---|---|
With bis(tri-t-butylphosphine)palladium(0); water; sodium chloride In dibutyl ether at 20℃; for 0.00555556h; pH=6; Schlenk technique; | 98% |
1-bromo-2-ethylbenzene
(beta-bromoethyl)monobromobenzene
Conditions | Yield |
---|---|
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 3h; Heating / reflux; | 97% |
With carbon tetrabromide; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In dichloromethane at 20℃; for 36h; Schlenk technique; Inert atmosphere; Irradiation; | |
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Inert atmosphere; Reflux; |
diethylchlorophosphine
1-bromo-2-ethylbenzene
diethyl(o-ethylphenyl)phosphane
Conditions | Yield |
---|---|
Stage #1: 1-bromo-2-ethylbenzene With n-butyllithium In diethyl ether at -10 - 0℃; for 3h; Stage #2: diethylchlorophosphine In diethyl ether at 20℃; Further stages.; | 97% |
1-bromo-2-ethylbenzene
N-(4-chlorobenzylidene)-N-(1,1,1-trimethylsilyl)amine
Conditions | Yield |
---|---|
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 90℃; for 14h; | 96% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere; | 96% |
With C25H29FeI2N3OPd; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 19h; Suzuki-Miyaura Coupling; Schlenk technique; Sealed tube; | |
With potassium carbonate In ethanol; water at 70℃; for 0.75h; Suzuki Coupling; | 72 %Chromat. |
With C36H36Cl2Fe2NPPd; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 18h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 57 %Chromat. |
1-bromo-2-ethylbenzene
N-trimethylsilyl(4-methoxy)benzaldimine
Conditions | Yield |
---|---|
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 90℃; for 14h; | 95% |
Conditions | Yield |
---|---|
With N-[2-(pyrazol-1-yl)phenyl]-N'-benzylimidazol-2-ylidene palladium chloride; potassium carbonate In water; N,N-dimethyl-formamide Reagent/catalyst; Heck Reaction; | 95% |
With dichlorobis(tri-O-tolylphosphine)palladium; N-Methyldicyclohexylamine; 4,4'-di-tert-butylbiphenyl; tetrabutyl-ammonium chloride In N,N-dimethyl acetamide at 80℃; for 24h; Reagent/catalyst; Heck Reaction; Glovebox; | |
With N,N-dimethyl-cyclohexanamine; tetrabutyl-ammonium chloride; palladium diacetate; triphenylphosphine In N,N-dimethyl acetamide at 80℃; for 24h; Heck Reaction; | 18 %Spectr. |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 150℃; for 12h; | 95% |
1-bromo-2-ethylbenzene
2,3-dihydro-2-methyl-1H-inden-1-one
Conditions | Yield |
---|---|
With (R)-BIDIME; palladium diacetate; sodium t-butanolate In toluene at 80℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere; enantioselective reaction; | 95% |
Conditions | Yield |
---|---|
Stage #1: 1-bromo-2-ethylbenzene With iodine; magnesium In tetrahydrofuran at -5 - 5℃; for 2h; Stage #2: propionaldehyde In tetrahydrofuran at 20℃; | 95% |
1-bromo-2-ethylbenzene
2-{[allyl(benzyl)amino]methyl}-N-(4-methoxyphenyl)aniline
4-benzyl-2-(2-ethylbenzyl)-1-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); cyclohexyldiphenylphosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 135℃; Inert atmosphere; | 94% |
isopropylboronic acid
1-bromo-2-ethylbenzene
1-ethyl-2-isopropylbenzene
Conditions | Yield |
---|---|
With potassium phosphate monohydrate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; C20H34O3P2 In toluene at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With bis(tri-t-butylphosphine)palladium(0); water; sodium chloride In hexane at 20℃; for 0.00555556h; pH=6; Schlenk technique; | 94% |
1-bromo-2-ethylbenzene
N-(2-furylmethylidene)-N-(1,1,1-trimethylsilyl)amine
Conditions | Yield |
---|---|
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 90℃; for 14h; | 92% |
1-bromo-2-ethylbenzene
methyl thioisocyanate
2-ethyl-N-methylthiobenzamide
Conditions | Yield |
---|---|
Stage #1: 1-bromo-2-ethylbenzene With magnesium In tetrahydrofuran Stage #2: methyl thioisocyanate In tetrahydrofuran at 20℃; for 16h; | 91% |
1-bromo-2-ethylbenzene
N-(2,4,6-trimethylphenyl)-1,2-diaminoethane
Conditions | Yield |
---|---|
With (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)ferrocene; palladium diacetate; sodium t-butanolate In 1,2-dimethoxyethane at 80℃; for 17h; Glovebox; Inert atmosphere; Sealed tube; | 91% |
1-bromo-2-ethylbenzene
DL-3-aminohexahydro-1H-azepin
Conditions | Yield |
---|---|
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In xylene at 130℃; for 24h; | 90% |
1-bromo-2-ethylbenzene
1,1-diphenyl-2-methyl-2-propen-1-ol
2-(2-ethylphenyl)methyl-2-methyl-3,3-diphenyloxirane
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); sodium t-butanolate; ruphos In toluene for 6h; Inert atmosphere; Reflux; | 90% |
Conditions | Yield |
---|---|
With N-Methyldicyclohexylamine; tetraethylammonium chloride; palladium diacetate In N,N-dimethyl acetamide at 85℃; for 60h; Arylation; Heck arylation; | A n/a B 89% |
1-bromo-2-ethylbenzene
(1R,4S,6S)-bicyclo<2.2.2>octane-6-ol-2-one
(1R,2R,4S,6S)-2-(2-ethylphenyl)bicyclo[2.2.2]octane-2,6-diol
Conditions | Yield |
---|---|
Stage #1: 1-bromo-2-ethylbenzene In tetrahydrofuran Stage #2: (1R,4S,6S)-bicyclo<2.2.2>octane-6-ol-2-one In tetrahydrofuran; diethyl ether at 25℃; for 1h; Grignard reaction; Further stages.; | 89% |
Conditions | Yield |
---|---|
With C40H32N4O7Ti2(2+)*2C8F17O3S(1-); zinc In toluene at 35℃; for 10h; | 89% |
1-bromo-2-ethylbenzene
(E)-tert-butyl 3-(4-((6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate
(E)-tert-butyl 3-(4-((2-(2-ethylphenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate
Conditions | Yield |
---|---|
With chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 150℃; for 2h; Microwave irradiation; Sealed tube; Inert atmosphere; | 89% |
The molecular structure of 2-Bromoethylbenzene (CAS NO.1973-22-4) is
IUPAC Name: 1-Bromo-2-ethylbenzene
Molecular Formula: C8H9 Br
Molecular Weight: 185.06
EINECS: 217-823-8
Density: 1.338
Melting Point: -56 °C
Boiling Point: 199.9 °C at 760 mmHg
Flash Point: 71 ºC
Appearance: Clear colourless to light yellow liquid
Freely Rotating Bonds: 1
Polar Surface Area: Å2
Index of Refraction: 1.54
Molar Refractivity: 43.49 cm3
Molar Volume: 138.4 cm3
Polarizability: 17.24 ×10-24 cm3
Surface Tension: 34 dyne/cm
Enthalpy of Vaporization: 41.83 kJ/mol
Vapour Pressure: 0.471 mmHg at 25°C
The Cas Register Number of 2-Bromoethylbenzene is 1973-22-4. The chemical synonyms of 2-Bromoethylbenzene (CAS NO.1973-22-4) are 2-Ethylbromobenzene ; 1-Bromo-2-ethylbenzene ; O-Bromoethylbenzene ; 1-Ethyl-2-brombenzol ; 1-Ethyl-2-bromobenzene ; 2-Bromo-1-ethylbenzene ; benzene,1-bromo-2-ethyl- ; o-ethylbromobenzene . Its product categories are Benzene derivates ; Bromine Compounds ; Aryl ; C8 ; Halogenated Hydrocarbons .
2-Bromoethylbenzene (CAS NO.1973-22-4) is used as organic reagent, pharmaceutical intermediate.
Hazard Codes: Xi,N,O
Risk Statements: 36/37/38-51/53
R36/37/38: Irritating to eyes, respiratory system and skin.
R51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 26-61-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
S24/25: Avoid contact with skin and eyes.
RIDADR: UN 3082 9/PG 3
WGK Germany: 3
F: 9
HazardClass: IRRITANT
HS Code: 29036990
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