Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane for 10h; Reflux; | 78% |
With dihydrogen peroxide; acetonitrile In aq. buffer at 20℃; for 1h; pH=11; Green chemistry; | 78% |
With dihydrogen peroxide; potassium carbonate In water; acetonitrile at 20℃; | 65% |
Conditions | Yield |
---|---|
With CuCl-alumina In various solvent(s) at 150℃; for 6h; | 75% |
With trans-bis(glycinato)copper(II) monohydrate; tetramethlyammonium chloride In ethanol at 100℃; for 36h; Finkelstein Reaction; Schlenk technique; Inert atmosphere; | 70% |
Conditions | Yield |
---|---|
With oxygen; silver carbonate; potassium hydroxide; copper dichloride In dimethyl sulfoxide; N,N-dimethyl-formamide at 130 - 140℃; | 83% |
With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; for 24h; Schlenk technique; | 45% |
With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper diacetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; under 760.051 Torr; for 20h; Schlenk technique; | 45% |
With copper(l) iodide; oxygen; copper(l) chloride In dimethyl sulfoxide at 160℃; under 760.051 Torr; for 30h; Schlenk technique; Sealed tube; | 35% |
Conditions | Yield |
---|---|
With zirconium(IV) oxynitrate hydrate; iodine In toluene at 20℃; for 16h; Inert atmosphere; | 84% |
With Iron(III) nitrate nonahydrate In toluene at 80℃; for 18h; Inert atmosphere; | 70% |
With nitric acid; trifluoroacetic acid In water at 80℃; for 18h; regioselective reaction; | 61% |
Conditions | Yield |
---|---|
With p-toluenesulfonyl nitrite; copper dichloride In acetonitrile at 25℃; for 0.0166667h; | 87% |
With hydrogenchloride; potassium nitrite; dimethyl sulfoxide In water at 35℃; for 0.5h; | 73% |
With tert.-butylnitrite; N-benzyl-N,N,N-triethylammonium chloride; copper dichloride; 10-camphorsulfonic acid In neat (no solvent) Time; Solvent; | 59% |
Conditions | Yield |
---|---|
With ammonia at 125℃; under 15001.5 Torr; for 1h; Autoclave; | 99.85% |
Conditions | Yield |
---|---|
With bromine; iodine; chlorine at 140℃; for 2h; Reagent/catalyst; Temperature; | 86.1% |
chlorobenzene
A
3-Chloronitrobenzene
B
4-chlorobenzonitrile
C
2-Chloronitrobenzene
Conditions | Yield |
---|---|
With dinitrogen tetraoxide; N,N,N,N-tetraethylammonium tetrafluoroborate In sulfolane at 30℃; electrochemical process; Yield given. Yields of byproduct given; | |
With zeolite H-beta; Nitrogen dioxide at 150℃; Yield given. Yields of byproduct given; | |
With zeolite FeAl-ZSM-5; Nitrogen dioxide at 150℃; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 3h; | A 86% B 14% |
With ammonium molybdate; water; nitric acid In chloroform for 6h; Nitration; Heating; | A 82% B 16% |
With ammonium nitrate; trifluoroacetic anhydride at 25℃; for 2h; | A 80% B 20% |
2-Chloronitrobenzene
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride In acetonitrile at 60℃; for 0.75h; Substitution; | 77% |
With N-benzyl-N,N,N-triethylammonium chloride; copper In acetonitrile at 20℃; for 0.75h; Substitution; | 74% |
chlorobenzene
A
4-chlorobenzonitrile
B
2-Chloronitrobenzene
C
1-chloro-2,4-dinitro-benzene
Conditions | Yield |
---|---|
With nitric acid; acetic anhydride at 0 - 20℃; for 0.166667h; Overall yield = 76 %; |
2-Chloronitrobenzene
Conditions | Yield |
---|---|
With hydrogenchloride; copper(l) chloride at 0 - 5℃; oder bei 100-105grad; |
2-Chloronitrobenzene
Conditions | Yield |
---|---|
With nitric acid at 65℃; |
2-Chloronitrobenzene
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride; silver(l) oxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 36h; Autoclave; | 62 %Chromat. |
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride; silver(l) oxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 18h; Autoclave; | 96 %Chromat. |
2-nitro-benzeneethanol
2-Chloronitrobenzene
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride; silver(l) oxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 18h; Autoclave; | 95 %Chromat. |
1-(2-nitrophenyl)ethan-1-ol
2-Chloronitrobenzene
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride; silver(l) oxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 18h; Reagent/catalyst; Solvent; Time; Autoclave; | 87 %Chromat. |
Conditions | Yield |
---|---|
With copper(l) iodide; 1,10-Phenanthroline; oxygen; potassium carbonate In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 18h; Reagent/catalyst; Autoclave; Molecular sieve; | 84 %Chromat. |
2-(1-Hydroxypropyl)nitrobenzene
2-Chloronitrobenzene
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride; silver(l) oxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 18h; Autoclave; | 92 %Chromat. |
2-bromo-1-(2-nitro-phenyl)-ethanol
2-Chloronitrobenzene
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride; silver(l) oxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 36h; Autoclave; | 98 %Chromat. |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid |
Conditions | Yield |
---|---|
With gold at -256.16℃; |
chlorobenzene
A
3-Chloronitrobenzene
B
4-chloro-2,6-dinitrophenol
C
4-chlorobenzonitrile
D
2-Chloronitrobenzene
Conditions | Yield |
---|---|
With oxygen; Nitrogen dioxide; iron(III)-acetylacetonate In 1,2-dichloro-ethane at 0℃; for 36h; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
Stage #1: 1,2-Dinitrobenzene With perchloric acid; sulfuric acid; sodium nitrite In water; ethyl acetate Electrochemical reaction; Stage #2: With hydrogenchloride; copper In water Sandmeyer Reaction; Electrochemical reaction; | 63% |
2-Chloronitrobenzene
Conditions | Yield |
---|---|
With water; copper; sodium nitrite |
Conditions | Yield |
---|---|
With hydrogen bromide; copper(l) chloride |
aniline hydrochloride
A
2,4-dichloronitrobenzene
B
4-chlorobenzonitrile
C
2-Chloronitrobenzene
Conditions | Yield |
---|---|
With 3,3-dimethyldioxirane In acetone at 20℃; | A 12% B 36% C 23% |
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); copper acetylacetonate; copper(l) cyanide; sodium carbonate In 1,4-dioxane at 130℃; for 24h; Sealed tube; Air; |
Conditions | Yield |
---|---|
With poly(4-vinylpyridine)-nitrating mixture complex In dichloromethane at 20℃; for 2h; Green chemistry; Overall yield = 81 %; |
methoxybenzene
A
3-Chloronitrobenzene
B
4-chlorobenzonitrile
C
2-Chloronitrobenzene
Conditions | Yield |
---|---|
With N-nitro-2,4,6-trimethylpyridinium tetrafluoroborate In nitromethane at 25℃; Rate constant; competitive nitration with benzene; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; | 99% |
With potassium phosphate; Al2O3#dotCo(2+) In water at 100℃; for 7h; | 90% |
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol; water at 80℃; for 1h; chemoselective reaction; | 100% |
With [1-butyl-2,3-dimethylimidazolium][tppm] stabilized rhodium nanoarticles at 50℃; under 22502.3 Torr; for 5h; Ionic liquid; Autoclave; chemoselective reaction; | 100% |
With hydrogen at 50℃; under 22502.3 Torr; for 5h; Autoclave; Sealed tube; Ionic liquid; chemoselective reaction; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 50℃; under 6375510 Torr; for 20h; | 100% |
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h; | 100% |
at 108℃; for 2h; Neat (no solvent); | 98% |
Conditions | Yield |
---|---|
With ISOPROPYLAMIDE; copper at 100℃; for 16h; | 100% |
With copper In N,N-dimethyl acetamide at 100℃; for 4h; Product distribution; with or without charcoal; | 89% |
With copper; pyrographite In N,N-dimethyl acetamide at 100℃; for 2h; | 89 % Turnov. |
With copper In N,N-dimethyl acetamide at 100℃; for 8h; | 59 % Chromat. |
2,4-dimethyl-thiophenol
2-Chloronitrobenzene
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 50℃; for 5h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2.5h; Inert atmosphere; | 99.79% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; | 97% |
3,5-Difluoro-4-methoxybenzylamine
2-Chloronitrobenzene
N-(3,5-difluoro-4-methoxybenzyl)-2-nitroaniline
Conditions | Yield |
---|---|
With ammonium acetate at 100℃; for 24h; | 100% |
Conditions | Yield |
---|---|
With indium; acetic acid In methanol at 20℃; for 1.5h; | 100% |
With samarium; acetic acid In methanol at 20℃; for 1.5h; | 80% |
With aluminum oxide; zinc In dichloromethane at 20℃; for 12h; Acetylation; reduction; | 75% |
4-dibenzothiophene boronic acid
2-Chloronitrobenzene
4-(2-nitrophenyl)dibenzo[b,d]thiophene
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; benzene at 70℃; for 7h; | 100% |
With potassium phosphate tribasic trihydrate; (2-(anthracen-9-yl)-1H-inden-3-yl)dicyclohexylphosphine; palladium diacetate In water; isopropyl alcohol; toluene at 90℃; for 16h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; | 87% |
2-Chloronitrobenzene
dibenzoselenophene-4-boronic acid
4-(2-nitrophenyl)dibenzoselenophene
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; benzene at 70℃; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide In water; N,N-dimethyl-formamide 1.) between -3 and +2 deg C, 40 min, 2.) 80 deg C, 1 h; | 99.9% |
With C40H30Cl2N2NiO2S2; sodium hydroxide In N,N-dimethyl-formamide at 70℃; for 2h; | 96% |
With potassium fluoride impregnated on clinoptilolite; air In dimethyl sulfoxide at 115 - 120℃; for 4h; | 95% |
Conditions | Yield |
---|---|
With copper In water at 100℃; for 12h; Ullmann reaction; | 99.3% |
In water at 130℃; for 24h; Autoclave; | 99% |
With copper In water at 100℃; for 8h; Sealed tube; | 95% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; | 99% |
With potassium carbonate; Cu/Al-HTB at 100℃; for 8h; | 91% |
With 2-carbomethoxy-3-hydroxyquinoxaline-di-N-oxide; caesium carbonate; copper(I) bromide at 115℃; for 24h; Inert atmosphere; Schlenk technique; | 81% |
With ethanol at 150℃; | |
With potassium carbonate In dimethyl sulfoxide at 60℃; for 17h; |
Conditions | Yield |
---|---|
In water at 105℃; for 24h; Sealed vessel; | 99% |
In dimethyl sulfoxide | 85% |
With ethanol at 170℃; |
3-Pyrroline
2-Chloronitrobenzene
1-(2-Nitro-phenyl)-2,5-dihydro-1H-pyrrole
Conditions | Yield |
---|---|
at 70℃; for 0.75h; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; | 99% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere; | 95% |
In nitrobenzene at 190 - 200℃; for 6h; | 46% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; | 99% |
In nitrobenzene at 190 - 200℃; for 6h; | 64% |
chloromethyl phenyl sulfone
2-Chloronitrobenzene
1-benzenesulfonylmethyl-3-chloro-2-nitro-benzene
Conditions | Yield |
---|---|
With potassium tert-butylate; acetic acid In tetrahydrofuran at -50 - 20℃; for 0.5h; | 99% |
α-phenoxy-α-phenylacetonitrile
2-Chloronitrobenzene
α-(3-Chloro-4-nitrophenyl)phenylacetonitrile
Conditions | Yield |
---|---|
Stage #1: α-phenoxy-α-phenylacetonitrile; 2-Chloronitrobenzene With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at -78℃; for 0.25h; Stage #2: With hydrogenchloride In water at -78℃; | 99% |
With sodium hydroxide In dimethyl sulfoxide for 1h; Ambient temperature; | 55% |
3,5-difluorobenzylamine
2-Chloronitrobenzene
N-(3,5-difluorobenzyl)-2-nitroaniline
Conditions | Yield |
---|---|
With ammonium acetate at 100℃; for 24h; | 99% |
Conditions | Yield |
---|---|
With caesium carbonate; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane for 1h; Suzuki-Miyaura coupling; Heating; | 99% |
With C12H10N3OPol; tetrabutylammomium bromide; palladium diacetate; potassium carbonate In water at 100℃; for 15h; Suzuki-Miyaura reaction; | 99% |
With potassium carbonate In water; isopropyl alcohol at 100℃; for 18h; Catalytic behavior; Suzuki-Miyaura Coupling; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 20 - 110℃; | 99% |
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 2h; Inert atmosphere; Green chemistry; | 99% |
With potassium carbonate; bis(μ-iodo)bis[(-)-sparteine]dicopper(I) In dimethyl sulfoxide at 125℃; for 12h; | 92% |
trans-2-phenylvinylboronic acid
2-Chloronitrobenzene
(E)-2-nitrostilbene
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate In 1,4-dioxane for 1h; Suzuki-Miyaura cross-coupling; Heating; | 99% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; ruphos In toluene at 135℃; for 24h; Buchward-Hartwig coupling; | 99% |
Conditions | Yield |
---|---|
With copper(l) iodide; 1-(dimethylamino-1-yl-pyridin-2-yl-methyl)naphthalen-2-ol; potassium carbonate In dimethyl sulfoxide at 120℃; for 24h; Ullmann Condensation; Green chemistry; | 99% |
Stage #1: 3-methyl-phenol With potassium hydroxide at 90℃; for 0.25h; Stage #2: 2-Chloronitrobenzene at 150℃; for 2h; |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine)platinum; phenylsilane; C30H51Cl3Mo3N6PPtS4(1+)*BF4(1-) In tetrahydrofuran at 70℃; under 760.051 Torr; Inert atmosphere; Schlenk technique; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
In methanol at 48 - 65℃; for 1h; Temperature; Large scale; | 98.9% |
4-Chlorophenylboronic acid
2-Chloronitrobenzene
4'-chloro-2-nitrobiphenyl
Conditions | Yield |
---|---|
With potassium carbonate In water; isopropyl alcohol at 100℃; for 10h; Suzuki-Miyaura Coupling; Inert atmosphere; | 98% |
With C84H64Cl3N3Pd; potassium carbonate In ethanol at 80℃; for 2h; Suzuki-Miyaura Coupling; | 98% |
With potassium phosphate; C46H52Cl3N3O2Pd In tetrahydrofuran; water at 60℃; for 4h; Suzuki-Miyaura Coupling; | 98% |
Conditions | Yield |
---|---|
With sodium ethanolate In methanol at 45 - 80℃; for 1.25h; Solvent; Temperature; Large scale; | 98.9% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; water; caesium carbonate; 1,2-bis-(diphenylphosphino)ethane; bis(pinacol)diborane In N,N-dimethyl-formamide at 140℃; for 24h; Schlenk technique; chemoselective reaction; | 73% |
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