Conditions | Yield |
---|---|
With iron(II) sulfate In water; dimethyl sulfoxide Ambient temperature; | 100% |
With HbO2(2+) In phosphate buffer; dimethyl sulfoxide for 1h; pH=7.4; | 89 % Chromat. |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 25 - 90℃; for 5.5h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With ammonium hydroxide at 150 - 220℃; under 90009 - 150015 Torr; | 98.6% |
With ammonium hydroxide at 150 - 220℃; under 90009 - 150015 Torr; | 98% |
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 4h; | 95% |
Conditions | Yield |
---|---|
With hydrogen at 20℃; under 760.051 Torr; for 1h; | 98% |
With hydrogen; 1-(2-benzimidazolyl)-C(CH3)=NH-NHCSNH2-Pd(II) In tetrahydrofuran at 20℃; for 2h; atmospheric pressure; | 95% |
With triethylamine In water at 80℃; for 2h; Inert atmosphere; Green chemistry; chemoselective reaction; | 95% |
Conditions | Yield |
---|---|
With 1-n-butyl-3-methylimidazolium azide; sulfuric acid; acetic acid at 54℃; for 4h; Schmidt Reaction; | 97% |
With sodium azide; chloroform; sulfuric acid | |
With thionyl chloride; hydroxylamine-O-sulfonic acid 1) 1h, reflux, 2) toluene, 2h, reflux; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 0.5h; Product distribution; Further Variations:; Solvents; reaction time; Heating; | 95% |
With sodium hydroxide In ethanol Reflux; | 80% |
With hydrogenchloride; water for 2h; Reflux; | 77% |
Conditions | Yield |
---|---|
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 130℃; for 6h; Reagent/catalyst; Time; Sealed tube; Inert atmosphere; | 95% |
Stage #1: 2-nitrophenyl bromide With copper(l) iodide; D-glucosamine hydrochloride; potassium carbonate In water; acetone at 90℃; for 0.166667h; Stage #2: With ammonia In water; acetone at 90℃; for 24h; | 83% |
With ammonium hydroxide; copper(l) iodide; potassium carbonate; 4R-4-hydroxyproline In dimethyl sulfoxide at 70℃; for 24h; | 78% |
Conditions | Yield |
---|---|
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h; Reagent/catalyst; | 95% |
With dihydrogen peroxide; acetonitrile In aq. buffer at 20℃; for 20h; pH=11; Green chemistry; | 86% |
With dihydrogen peroxide; potassium carbonate In water; acetonitrile at 20℃; | 75% |
With sodium peroxide | |
palladium-carbon In triethylene glycol dimethyl ether |
Conditions | Yield |
---|---|
Stage #1: o-azidonitrobenzene With hydrazine hydrate for 0.166667h; Inert atmosphere; Stage #2: for 4h; Catalytic behavior; Reagent/catalyst; Irradiation; chemoselective reaction; | 95% |
With methanol; sodium tetrahydroborate In tetrahydrofuran for 1h; Heating; | 94% |
Stage #1: o-azidonitrobenzene With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; tert-butyl alcohol In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With sodium t-butanolate In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; chemoselective reaction; | 94% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 1h; Product distribution; Further Variations:; Solvents; reaction time; Heating; | 95% |
With lithium aluminium tetrahydride In diethyl ether at 27℃; for 1h; | 66 % Turnov. |
2-(2-nitrophenoxy)propanamide
2-nitro-aniline
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 3h; Green chemistry; | 95% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide; Chloroacetamide In N,N-dimethyl-formamide at 90 - 150℃; for 4h; Reagent/catalyst; Smiles Aromatic Rearrangement; | 92% |
With ammonia; water at 160 - 170℃; | |
With sodium tetrahydroborate In water at 20℃; |
Conditions | Yield |
---|---|
With phosphoric acid In sulfolane at 120℃; Reagent/catalyst; Solvent; Temperature; | 91% |
With hydrogenchloride at 170 - 180℃; Erhitzen des Kaliumsalzes; | |
With sulfuric acid; water |
Conditions | Yield |
---|---|
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 4h; | A 88% B 12% |
With potassium hydrogensulfate; potassium metaperiodate; silica gel; sodium nitrite In neat (no solvent) for 0.0833333h; Reagent/catalyst; Solvent; Microwave irradiation; | A 86% B n/a |
With Iron(III) nitrate nonahydrate at 84.84℃; for 0.25h; regioselective reaction; | A 77% B 23% |
Conditions | Yield |
---|---|
With copper(l) iodide; tetra(n-butyl)ammonium hydroxide; ammonia In water at 25℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction; | 87% |
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 110℃; for 6h; Sealed tube; Inert atmosphere; | 84% |
With acetamidine hydrochloride; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 20h; Inert atmosphere; Green chemistry; | 82% |
2-(trimethylsilanyl)ethanesulfonic acid (2-nitrophenyl)amide
2-nitro-aniline
Conditions | Yield |
---|---|
With cesium fluoride In N,N-dimethyl-formamide at 130℃; for 36h; | 87% |
2-nitro-aniline
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane at 110℃; for 22h; | 84% |
4-tert-butyl-2-(2-nitrophenylazo)phenol
A
2-Methyl-1H-benzimidazole
B
N-formyldiethylamine
C
2-(5-tert-butyl-2-hydroxyphenyl)benzotriazole
D
2-nitro-aniline
Conditions | Yield |
---|---|
With carbon monoxide; triethylamine In 1,2-dichloro-benzene at 200℃; under 60800 Torr; for 8h; Further byproducts given; | A n/a B n/a C 63% D 82% |
4-methyl-2-(2-nitrophenylazo)phenol
A
2-Methyl-1H-benzimidazole
B
5-methylbenzo[d]oxazol-2(3H)-one
C
2-nitro-aniline
D
2-(2-Hydroxy-5-methylphenyl)benzotriazole
Conditions | Yield |
---|---|
With carbon monoxide; triethylamine In 1,2-dichloro-benzene at 200℃; under 60800 Torr; for 8h; Further byproducts given; | A n/a B n/a C 7% D 82% |
o-azidonitrobenzene
(3R,4S)-2,3,4,5-Tetraphenyl-3,4-dihydro-2H-[1,2,3]diazaphosphole
A
2-nitro-aniline
2,3,4r,5-tetraphenyl-3,4-dihydro-2H-[1,2,3]diazaphosphole 3c-oxide
Conditions | Yield |
---|---|
In benzene for 2h; Ambient temperature; | A 20% B n/a C 80% |
Conditions | Yield |
---|---|
With iron(II) sulfate In water; dimethyl sulfoxide for 1.5h; Ambient temperature; | A 80% B 20% |
Conditions | Yield |
---|---|
With ammonium hydroxide; sodium sulfite In methanol at 70℃; for 144h; | 80% |
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid; aniline for 19h; Heating; | 80% |
With sodium acetate In ethanol at 30℃; under 600 Torr; for 0.5h; Reagent/catalyst; Temperature; Inert atmosphere; | 74.6% |
Conditions | Yield |
---|---|
Stage #1: o-azidonitrobenzene With hydrazine hydrate for 0.166667h; Inert atmosphere; Stage #2: for 4h; Irradiation; | A 20% B 80% |
Conditions | Yield |
---|---|
Stage #1: 1,2-Dinitrobenzene With sodium tetrahydroborate In water at 20℃; for 0.25h; Inert atmosphere; Green chemistry; Stage #2: In water at 20℃; for 0.75h; Inert atmosphere; Green chemistry; | A 78% B 15% |
With sodium tetrahydroborate; water at 0 - 20℃; for 24h; | A 24% B 53% |
With titanium dioxide In ethanol for 1.5h; Irradiation; Green chemistry; | A 55 %Chromat. B 30 %Chromat. |
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; potassium phosphate tribasic heptahydrate; water; Sucrose In water at 90℃; for 15h; Catalytic behavior; Green chemistry; | 78% |
2-nitro-aniline
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane at 110℃; for 22h; | 78% |
Conditions | Yield |
---|---|
With sodium hydroxide; benzyltrimethylazanium tribroman-2-uide In water at 70℃; for 1h; | 76% |
Conditions | Yield |
---|---|
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h; Product distribution; Mechanism; other sulfenamide reagents, other nitroarenes; | A 71% B 14% |
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h; | A 71% B 14% |
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h; | A 71% B 14% |
Conditions | Yield |
---|---|
In acetic acid at 20℃; for 36h; Heating / reflux; | 100% |
With acetic acid for 24h; Heating; | 89% |
With N,N-dimethyl-formamide for 0.0666667h; microwave irradiation; | 84% |
2-nitro-aniline
p-toluenesulfonyl chloride
4-methyl-N-(2-nitrophenyl)benzene sulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 4℃; | 100% |
With pyridine In dichloromethane at 20℃; for 48h; | 90% |
With pyridine In dichloromethane at 20℃; for 16h; | 75% |
2-nitro-aniline
4-iodo-2-nitroaniline
Conditions | Yield |
---|---|
With N-iodo-succinimide In acetic acid at 95℃; for 1h; | 100% |
With sodium periodate; potassium iodide; sodium chloride In water; acetic acid at 25℃; for 8h; | 98% |
With sodium periodate; sulfuric acid; iodine; potassium iodide; sodium sulfite In water; acetic acid at 25℃; for 4h; Reagent/catalyst; | 98% |
Conditions | Yield |
---|---|
Stage #1: 2-nitro-aniline With boron trifluoride diethyl etherate In dichloromethane at -15℃; for 0.25h; Stage #2: With tert.-butylnitrite In dichloromethane at -15 - 0℃; for 1h; | 100% |
With tert.-butylnitrite; boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; | 95% |
With dinitrogen tetraoxide; benzene entsteht das Nitrat; |
Conditions | Yield |
---|---|
With hydrazine hydrate at 90℃; for 1.16667h; chemoselective reaction; | 100% |
With hydrazine hydrate In ethanol; water at 80℃; for 3h; chemoselective reaction; | 100% |
With sodium tetrahydroborate In water for 0.116667h; Kinetics; Catalytic behavior; Reagent/catalyst; | 100% |
Conditions | Yield |
---|---|
Stage #1: cyanoacetic acid With phosphorus pentachloride In dichloromethane for 0.5h; Reflux; Stage #2: 2-nitro-aniline In dichloromethane for 2h; Reflux; | 100% |
With dicyclohexyldiimide In N,N-dimethyl-formamide for 1h; Ambient temperature; | 74% |
With phosphorus pentachloride In benzene |
methyl trans-3-(4-methoxyphenyl)glycidate
2-nitro-aniline
2-Hydroxy-3-(4-methoxy-phenyl)-3-(2-nitro-phenylamino)-propionic acid methyl ester
Conditions | Yield |
---|---|
zinc(II) iodide In toluene at 22℃; for 21h; Product distribution; various solvents, additives, temperatures, times; | 100% |
zinc(II) iodide In toluene at 22℃; for 21h; | 100% |
di-tert-butyl dicarbonate
2-nitro-aniline
(2-nitro-phenyl)-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: 2-nitro-aniline With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.666667h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 1h; | 100% |
With 12-TPA/SBA 15 at 20℃; for 0.1h; Neat (no solvent); | 97% |
Stage #1: 2-nitro-aniline With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.666667h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 2h; | 96% |
2-nitro-aniline
p-tert-butyl benzoyl chloride
N-(2-nitrophenyl)-4-(1,1-dimethylethyl)-benzamide
Conditions | Yield |
---|---|
With pyridine Acylation; | 100% |
With pyridine In dichloromethane Acylation; |
Conditions | Yield |
---|---|
With tin(ll) chloride at 130℃; for 0.0833333h; microwave; | 100% |
With hydrogenchloride; iron In water at 70 - 100℃; |
2-bromo-1-chlorobenzene
2-nitro-aniline
N-(2-chlorophenyl)-N-(2-nitrophenyl)amine
Conditions | Yield |
---|---|
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In toluene at 120℃; for 24h; Buchwald-Hartwig coupling; Inert atmosphere; | 100% |
With caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene Buchwald-Hartwig reaction; | 99% |
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In toluene at 120℃; Inert atmosphere; | 86% |
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium (0) In toluene at 110℃; for 30h; | 65% |
Conditions | Yield |
---|---|
With tin(ll) chloride at 130℃; for 0.0833333h; microwave; | 100% |
bis(trichloromethyl) carbonate
2-nitro-aniline
2-nitrophenyl isocyanate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 100% |
In toluene for 3h; Heating; | |
In dichloromethane at 0℃; for 0.5h; |
Conditions | Yield |
---|---|
With aluminum tri-bromide at -20℃; | 100% |
Stage #1: Cyclopentane; carbon monoxide With aluminum tri-bromide; carbon tetrabromide In various solvent(s) at 0℃; under 760.051 Torr; for 4h; Stage #2: 2-nitro-aniline In various solvent(s) at -20 - 20℃; under 760.051 Torr; Further stages.; | 100 % Chromat. |
Stage #1: Cyclopentane; carbon monoxide With 2AlBr3*CBr4 In dibromomethane Stage #2: 2-nitro-aniline In dibromomethane at 0℃; for 2h; chemoselective reaction; | 97 %Chromat. |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; | 100% |
5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione
2-nitro-aniline
2,2-dimethyl-5-((2-nitrophenylamino)methylene)-1,3-dioxane-4,6-dione
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 0.25h; | 100% |
Conditions | Yield |
---|---|
With palladium with copper supported on alumina In water at 179.84℃; under 26252.6 Torr; for 12h; Autoclave; | 100% |
With JRC-TIO-7-supported iridium catalyst In 1,3,5-trimethyl-benzene at 80℃; for 18h; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique; | 99% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In toluene at 160℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Schlenk technique; Inert atmosphere; Sealed tube; | 97% |
Conditions | Yield |
---|---|
at 20℃; for 0.133333h; Milling; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; for 0.0833333h; Green chemistry; | 99.2% |
With copper dichloride; 1-hexyl-3-methylimidazol-1-ium chloride at 40℃; for 16h; regioselective reaction; | 85% |
With N-chloro-succinimide In acetonitrile for 10h; Heating; | 57% |
Multi-step reaction with 2 steps 1: diethyl ether; hypochlorous acid / 20 °C 2: hydrochloric acid; diethyl ether / -20 °C View Scheme |
Conditions | Yield |
---|---|
With triethylamine; dmap In dichloromethane at 0 - 20℃; for 18h; | 99% |
With pyridine at 25℃; for 15h; | 97% |
With pyridine; dmap | 93% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; | 99% |
With montmorillonite K-10 In dichloromethane for 1.5h; Ambient temperature; | 98% |
With carbon-silica composite from starch (7.5 molpercent SO3H) at 60℃; for 0.75h; solvent-free conditions; | 95% |
Conditions | Yield |
---|---|
With hydrogen bromide; dihydrogen peroxide In methanol at 0 - 20℃; for 12h; | 99% |
With HMTAB In dichloromethane at 20℃; for 0.5h; | 98% |
With 1-butyl-3-methylpyridinium tribromide at 20℃; | 98% |
Conditions | Yield |
---|---|
With bromine In methanol; dichloromethane at 20℃; for 1h; | 99% |
With bromine; acetic acid at 45℃; for 4h; | 98% |
With bromine; acetic acid at 45℃; for 4h; | 98% |
3-methylbutyric acid trimethylsilyl ester
2-nitro-aniline
3-methyl-2'-nitrobutananilide
Conditions | Yield |
---|---|
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature; | 99% |
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 120℃; for 36h; | 99% |
With potassium carbonate In dimethyl sulfoxide at 120℃; for 36h; Inert atmosphere; | 95% |
With potassium carbonate In dimethyl sulfoxide at 130℃; for 20h; Inert atmosphere; Schlenk technique; | 94% |
2-nitro-aniline
acetylacetone
3-(2-(2-nitrophenyl)hydrazineylidene)pentane-2,4-dione
Conditions | Yield |
---|---|
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium nitrite Stage #2: acetylacetone With sodium hydroxide; sodium acetate In methanol; water at 0 - 20℃; for 1h; Further stages.; | 99% |
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: acetylacetone With sodium acetate In methanol; water at 20℃; | 87% |
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium hydroxide; sodium nitrite In water at -0.16℃; Stage #2: acetylacetone In water at -0.16℃; for 1h; | 79% |
With hydrogenchloride; sodium acetate; sodium nitrite 1.) water, 0 deg C, 2.) acetone, 6 h; Multistep reaction; | |
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium nitrite at 0℃; for 0.5h; Stage #2: acetylacetone With sodium acetate In ethanol; water at 0 - 20℃; for 3h; Further stages.; |
Conditions | Yield |
---|---|
Stage #1: 2-nitro-aniline With sulfuric acid; sodium nitrite In water at 20℃; for 0.333333h; Stage #2: β-naphthol In water at 20℃; for 2h; | 99% |
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 4.25h; Stage #2: With aminosulfonic acid In water at 0℃; for 1h; Stage #3: β-naphthol In ethanol; water at 20℃; for 19.5h; | 93% |
Stage #1: 2-nitro-aniline With sodium nitrite In water at 20℃; Milling; Green chemistry; Stage #2: β-naphthol In water at 20℃; for 0.5h; Milling; Green chemistry; | 83% |
2-nitro-aniline
acrylic acid methyl ester
(E)-methyl 2-nitrocinnamate
Conditions | Yield |
---|---|
With tert.-butylnitrite; methanesulfonic acid; palladium diacetate; methoxybenzene In methanol at 0 - 25℃; for 48h; Reagent/catalyst; Heck Reaction; | 99% |
Stage #1: 2-nitro-aniline With tert.-butylnitrite In methanol at 0℃; for 0.5h; Stage #2: acrylic acid methyl ester With methanesulfonic acid; palladium diacetate In methanol at 0 - 25℃; Heck-Matsuda reaction; | 98% |
Stage #1: 2-nitro-aniline With tert.-butylnitrite In methanol at 0℃; for 0.5h; Heck-Matsuda reaction; Stage #2: acrylic acid methyl ester With methanesulfonic acid; palladium diacetate In methanol at 0 - 25℃; for 48h; Heck-Matsuda reaction; | 98% |
Conditions | Yield |
---|---|
With hydrogen In ethyl acetate at 20℃; under 7500.75 Torr; for 20h; Catalytic behavior; Activation energy; Reagent/catalyst; Temperature; Autoclave; Green chemistry; | 99% |
With hydrogen In ethyl acetate at 60℃; under 7500.75 Torr; for 20h; Reagent/catalyst; Solvent; Pressure; Time; Temperature; | 99% |
Stage #1: benzaldehyde; 2-nitro-aniline In 1,4-dioxane; water at 90℃; for 0.0833333h; Stage #2: With formic acid In 1,4-dioxane; water at 90℃; for 8h; Temperature; Sealed tube; | 96% |
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