Conditions | Yield |
---|---|
With formic acid In acetonitrile at 20℃; for 1h; Irradiation; | 100% |
In water at 25℃; for 0.333333h; Sonication; | 99% |
With sodium tetrahydroborate In water at 95℃; for 0.333333h; Green chemistry; | 98% |
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol; tetrabutylammonium perchlorate In N,N-dimethyl-formamide electrolytic reduction at a Pt gauze electrode at a potential of -0.30 V; | 100% |
With Decaborane; palladium on activated charcoal In methanol at 20℃; for 0.25h; | 99% |
With triethylsilane; indium(III) chloride In acetonitrile at -20℃; for 0.25h; | 99% |
(4-nitro-phenyl)-m-tolyl sulfone
A
di(p-nitrophenyl) disulfide
B
Toluene-3-thiosulfonic acid; compound with ammonia
C
4-nitro-aniline
Conditions | Yield |
---|---|
With sulfur; ammonia at 100℃; for 2h; titanium autoclave; | A 43% B 100% C 40% |
1-methoxy-4-((4-nitrophenyl)sulfonyl)benzene
A
di(p-nitrophenyl) disulfide
B
4-Methoxy-benzenethiosulfonic acid; compound with ammonia
C
4-nitro-aniline
Conditions | Yield |
---|---|
With sulfur; ammonia at 100℃; for 2h; titanium autoclave; | A 56% B 100% C 32% |
With sulfur; ammonia at 100℃; for 2h; Product distribution; titanium autoclave; various reactions temp. and amounts of S8; |
Conditions | Yield |
---|---|
With graphitic carbon nitride; hydrazine hydrate In water at 70℃; for 8h; Time; Darkness; Sealed tube; Green chemistry; chemoselective reaction; | 100% |
Conditions | Yield |
---|---|
With ammonium hydroxide at 120 - 190℃; under 45004.5 - 46504.7 Torr; for 4h; Temperature; Pressure; | 99.31% |
With ammonium hydroxide; copper(l) iodide at 200℃; for 6.5h; Reagent/catalyst; Temperature; Time; Autoclave; Green chemistry; | 97% |
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 4h; | 96% |
tert-butyl N-(4-nitrophenyl)carbamate
4-nitro-aniline
Conditions | Yield |
---|---|
With EPZG clay In dichloromethane for 1.5h; deacylation; Heating; | 99% |
With H-β zeolite In dichloromethane for 4h; Heating; | 98% |
With water at 150℃; for 10h; Subcritical conditions; | 97% |
Conditions | Yield |
---|---|
With copper(l) iodide; ascorbic acid In ammonia at 25℃; for 18h; Kinetics; liquid NH3; | 99% |
With ammonium hydroxide; copper(l) iodide; phosphate potassium salt In N,N-dimethyl-formamide at 20℃; for 36h; Inert atmosphere; | 98% |
Stage #1: p-nitrobenzene iodide 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 28h; | 98% |
Conditions | Yield |
---|---|
Stage #1: para-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 28h; | 98% |
With ammonium hydroxide at 20℃; for 3h; Catalytic behavior; | 98% |
With ammonia; triethylamine In water at 20℃; for 2.5h; | 98% |
L-methionine
3,5-dinitro-1-(4-nitrophenyl)-4-pyridone
A
4-nitro-aniline
B
(S)-2-(3,5-Dinitro-4-oxo-4H-pyridin-1-yl)-4-methylsulfanyl-butyric acid
Conditions | Yield |
---|---|
In pyridine; water for 3h; Ambient temperature; | A n/a B 98% |
α-naphthol
4'-nitrobenzenesulfenanilide
A
2-phenylthio-1-naphthol
B
4-(phenylthio)naphthalen-1-ol
C
4-nitro-aniline
D
2,4-bis(phenylthio)naphthalen-1-ol
Conditions | Yield |
---|---|
With trifluoroacetic acid In benzene for 0.166667h; Ambient temperature; Further byproducts given; | A 42% B 33% C 98% D 10% |
α-naphthol
4'-nitrobenzenesulfenanilide
A
2-phenylthio-1-naphthol
B
4-(phenylthio)naphthalen-1-ol
C
4-nitro-aniline
D
diphenyldisulfane
Conditions | Yield |
---|---|
With trifluoroacetic acid In benzene for 0.166667h; Ambient temperature; Further byproducts given; | A 42% B 33% C 98% D 14% |
α-naphthol
4'-nitrobenzenesulfenanilide
A
2-phenylthio-1-naphthol
B
4-(phenylthio)naphthalen-1-ol
C
4-nitro-aniline
D
2,4-bis(phenylthio)naphthalen-1-ol
E
diphenyldisulfane
Conditions | Yield |
---|---|
With trifluoroacetic acid In benzene for 0.166667h; Product distribution; Mechanism; 1.5 eqiv. TFA; | A 42% B 33% C 98% D 10% E 14% |
4'-nitrobenzenesulfenanilide
A
S-Phenyl benzenethiosulfonate
B
4-nitro-aniline
C
diphenyldisulfane
Conditions | Yield |
---|---|
With trifluoroacetic acid In benzene at 25℃; Product distribution; Mechanism; further sulfenanilide; | A 32% B 98% C 56% |
trifluoroacetic acid
A
butyl sulfoxide
B
2,2,2-trifluoro-N-(4-nitrophenyl)acetamide
C
4-nitro-aniline
Conditions | Yield |
---|---|
at 72℃; for 72h; Elimination; acylation; retro-Pummerer reaction; | A 79% B 98% C 2% |
Conditions | Yield |
---|---|
With ammonium iodide; hydrazine hydrate In ethanol at 60℃; for 42h; Inert atmosphere; Sealed tube; | 97% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 1h; Product distribution; Further Variations:; Solvents; reaction time; Heating; | 96% |
With 40% potassium fluoride/alumina at 85℃; for 0.0666667h; Microwave irradiation; Neat (no solvent); | 94% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 1.5h; Product distribution; Further Variations:; Solvents; reaction time; Heating; | 97% |
In methanol |
4-Nitro-N-phenylhydroxylamine
C11H14N2O4
A
4-nitrosonitrobenzene
B
4-nitro-aniline
Conditions | Yield |
---|---|
With iron(II) chloride In water; acetonitrile at 40℃; pH=4.7, ionic strength=0.5 M; | A 39% B 95% |
With iron(II) chloride In water; acetonitrile at 40℃; Mechanism; pH=4.7, ionic strength=0.5 M; |
C11H14N2O4
4-nitro-aniline
Conditions | Yield |
---|---|
With iron(II) chloride In water; acetonitrile at 40℃; pH=4.7, ionic strength=0.5 M; | 95% |
With FeCl2 or CuCl In water; acetonitrile at 40℃; Product distribution; Mechanism; pH=4.7, ionic strength=0.5 M; |
3-methyl-1-(4-nitrophenyl)-5-nitrouracil
methylamine
A
1,3-dimethyl-5-nitrouracil
B
4-nitro-aniline
Conditions | Yield |
---|---|
In methanol for 0.5h; Ambient temperature; | A 95% B n/a |
4-nitrophenyl azide
diethyl malonate
A
1,3-diethyl 2-diazopropanedioate
B
4-nitro-aniline
Conditions | Yield |
---|---|
With tetrabutylammonium perchlorate In N,N-dimethyl-formamide electrolytic reduction at a Pt gauze electrode at a potential of -0.30 V; | A 95% B 101 % |
ethyl α-ethoxycarbonyl-β-(4-nitroanilino)acrylate
4-nitro-aniline
Conditions | Yield |
---|---|
With ethylenediamine In ethanol at 20℃; for 2.3h; | 95% |
pyridine
3,5-dinitro-1-(4-nitrophenyl)-4-pyridone
A
4-nitro-aniline
B
1-Hydroxy-3,5-dinitro-1H-pyridin-4-one; compound with pyridine
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride at 20℃; for 2h; | A 94% B 83% |
C14H13NO5S
A
di(p-nitrophenyl) disulfide
B
3-Ethoxy-benzenethiosulfonic acid; compound with ammonia
C
4-nitro-aniline
Conditions | Yield |
---|---|
With sulfur; ammonia at 100℃; for 2h; titanium autoclave; | A 47% B 94% C 40% |
C11H14N2O4
N-(4-chlorophenyl)hydroxylamine
A
1-chloro-4-nitroso-benzene
B
4-nitro-aniline
Conditions | Yield |
---|---|
With iron(II) chloride In water; acetonitrile at 40℃; pH=4.7, ionic strength=0.5 M; | A 53% B 94% |
With iron(II) chloride In water; acetonitrile at 40℃; Mechanism; pH=4.7, ionic strength=0.5 M; |
Conditions | Yield |
---|---|
With pyrene; tetramethyl ammoniumhydroxide; benzamide; potassium carbonate In dimethyl sulfoxide at 90℃; for 2.08333 - 2.16667h; Conversion of starting material; | A 94% B 6% |
With potassium hydroxide; pyrene; potassium carbonate; urea In dimethyl sulfoxide at 90℃; for 2.08333 - 2.16667h; Conversion of starting material; | A 87% B 12% |
With urea, monopotassium salt; urea In dimethyl sulfoxide at 90℃; for 2h; | A 56% B 5.5% |
Conditions | Yield |
---|---|
With Vilsmeier reagent; potassium nitrate In neat (no solvent) at 100℃; under 1500.15 Torr; Reagent/catalyst; Temperature; Microwave irradiation; | 93% |
With nitric acid; sodium dodecyl-sulfate In water at 25℃; for 0.333333h; Micellar solution; Green chemistry; regioselective reaction; | 86% |
With nitric acid; sodium dodecyl-sulfate In acetonitrile at 24.84℃; for 3h; Micellar solution; regioselective reaction; | 85% |
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride at 20℃; for 2h; | A 93% B 88% |
Conditions | Yield |
---|---|
With 1,2-bis(mercaptomethyl)benzene; (Et4N) In acetonitrile at 26℃; for 1.5h; | A 93% B 2% |
With D-glucose; bakers' yeast In phosphate buffer; ethanol at 30℃; for 0.5h; pH=6.5; Product distribution; Further Variations:; time; | A 83% B n/a |
With sodium tetrahydroborate; selenium In ethanol at 23 - 26℃; for 0.25h; | A 81% B 16% |
With 1,2-bis(mercaptomethyl)benzene; (Et4N) In acetonitrile at 26℃; for 1.5h; Product distribution; |
1,3-Dichloro-5-(4-nitro-benzenesulfonyl)-benzene
A
di(p-nitrophenyl) disulfide
B
3,5-Dichloro-benzenethiosulfonic acid; compound with ammonia
C
4-nitro-aniline
Conditions | Yield |
---|---|
With sulfur; ammonia at 100℃; for 2h; titanium autoclave; | A 42% B 93% C 40% |
4-nitrobenzaldehdye
4-nitro-aniline
N-(4-nitrobenzylidene)-4-nitroaniline
Conditions | Yield |
---|---|
at 60℃; for 2h; | 100% |
at 83 - 85℃; | 100% |
With sulfuric acid In neat (no solvent) Microwave irradiation; Sealed tube; Green chemistry; | 72% |
benzaldehyde
4-nitro-aniline
4-nitro-N-(phenylmethylene)benzenamine
Conditions | Yield |
---|---|
In toluene at 120℃; for 24h; | 100% |
With aqueous extract of pericarp of Sapindus trifoliatus fruits at 20℃; for 0.0333333h; | 98% |
sodium hydrogen sulfate; silica gel at 52 - 54℃; for 0.0222222h; microwave irradiation; | 95% |
Conditions | Yield |
---|---|
With NMM In dichloromethane | 100% |
With triethylamine In dichloromethane at 20℃; | 71% |
With sodium hydroxide; acetone |
4-nitro-aniline
p-toluenesulfonyl chloride
N-(4-nitrophenyl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 4℃; | 100% |
With (Na1752K0.144Ca0365Mg0.065)(Al2044Si2774O96)*19.16H2O In ethanol at 25 - 30℃; for 2h; Sonication; Green chemistry; | 96% |
With pyridine In dichloromethane at 20℃; for 12h; | 94% |
4-nitro-aniline
2-chloropropionyl chloride
3-chloro-N-(4-nitrophenyl)propanamide
Conditions | Yield |
---|---|
at 0 - 50℃; Neat (no solvent); | 100% |
at 20 - 50℃; | 100% |
at 50℃; for 16h; | 97% |
4-nitro-aniline
diethyl 2-ethoxymethylenemalonate
ethyl α-ethoxycarbonyl-β-(4-nitroanilino)acrylate
Conditions | Yield |
---|---|
at 120℃; for 3h; Heating / reflux; | 100% |
for 0.025h; Gould-Jacob reaction; Irradiation; | 98% |
In ethanol at 28℃; for 6h; | 95% |
Conditions | Yield |
---|---|
With potassium iodide; 10-camphorsulfonic acid; sodium nitrite In acetic acid at 20℃; for 24h; Time; | 100% |
With Nitrogen dioxide; sodium iodide In acetonitrile at -20℃; for 10h; | 98% |
Stage #1: 4-nitro-aniline With toluene-4-sulfonic acid In water at 20℃; Stage #2: With potassium iodide In water at 20℃; for 1.5h; | 95% |
Conditions | Yield |
---|---|
Stage #1: 4-nitro-aniline With toluene-4-sulfonic acid; sodium nitrite In water at 20℃; for 0.333333h; Stage #2: With sodium azide In water at 20℃; Reagent/catalyst; | 100% |
Stage #1: 4-nitro-aniline With trifluoroacetic acid; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: With sodium azide In water at 20℃; for 5h; | 99% |
Stage #1: 4-nitro-aniline With hydrogenchloride In water at 0℃; Stage #2: With sodium nitrite In water for 0.166667h; Further stages; | 99% |
Conditions | Yield |
---|---|
With nitrosylchloride under 750.075 Torr; for 24h; | 100% |
With sodium nitrite In hydrogenchloride; water at 0.2℃; Rate constant; | |
With hydrogenchloride; sodium nitrite In hydrogenchloride; water at 25℃; Rate constant; |
Conditions | Yield |
---|---|
With t-butyl thionitrite; copper dichloride In acetonitrile at 25℃; for 2h; | 100% |
With t-butyl thionitrite; copper dichloride In acetonitrile at 25℃; for 0.0333333h; Product distribution; Mechanism; var. temperature, var. time, other copper(II) halides, other reagents, other substituted aniline derivatives; | 98% |
Stage #1: 4-nitro-aniline With tert.-butylnitrite In acetonitrile at 20℃; Sandmeyer Reaction; Flow reactor; Stage #2: With copper dichloride In ethylene glycol; acetonitrile at 82℃; Sandmeyer Reaction; Flow reactor; | 91% |
Conditions | Yield |
---|---|
With palladium diacetate; carbon monoxide; triphenylphosphine In water; acetic acid at 56℃; under 532 Torr; for 11h; | 100% |
With triethylsilane; palladium dichloride In ethanol at 20℃; for 1h; Inert atmosphere; | 100% |
With 10% palladium on activated charcoal; hydrogen for 2h; | 100% |
Conditions | Yield |
---|---|
With potassium hydrogensulfate; water; sodium nitrite for 0.0333333h; Diazotization; coupling; microwave irradiation; | 100% |
With hydrogenchloride; sodium nitrite In water at 20℃; for 1h; Time; | 99% |
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.0833333h; Reagent/catalyst; Temperature; Green chemistry; | 99% |
Conditions | Yield |
---|---|
Stage #1: 4-nitro-aniline With hydrogenchloride; sodium nitrite In water at 2℃; for 1.5h; Stage #2: phenol With sodium hydroxide In water at 2 - 20℃; for 4h; | 100% |
Stage #1: 4-nitro-aniline With carboxyl- and nitrite- functionalized graphene quantum dots at 20℃; for 0.0833333h; Stage #2: phenol In water at 20℃; for 0.166667h; | 96% |
Stage #1: 4-nitro-aniline With hydrogenchloride In water; acetone at 0℃; Inert atmosphere; Stage #2: With sodium nitrite In water; acetone at 0℃; for 1h; Inert atmosphere; Stage #3: phenol With sodium carbonate; sodium hydroxide In water; acetone at 0 - 20℃; for 3h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium acetate; sodium nitrite In acetic acid at 0℃; for 1h; | 100% |
4-methoxy-benzaldehyde
4-nitro-aniline
N-(4-methoxybenzylidene)-4-nitroaniline
Conditions | Yield |
---|---|
With pyrrolidine In dichloromethane at 20℃; for 16h; Molecular sieve; | 100% |
With TiO2 nanotubes at 20℃; for 8h; Neat (no solvent); Sunlight; | 98% |
sodium hydrogen sulfate; silica gel at 64 - 66℃; for 0.025h; microwave irradiation; | 96% |
6,7-dideoxy-α,β-D-galacto-hept-6-enopyranose
4-nitro-aniline
N-p-nitrophenyl-6,7-dideoxy-L-galacto-hept-6-enosylamine
Conditions | Yield |
---|---|
In methanol; acetic acid at 110℃; for 0.166667h; | 100% |
4-nitro-aniline
phenylacetyl chloride
N-(4-nitrophenyl)-2-phenylacetamide
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran at 0 - 20℃; for 2h; | 100% |
With potassium phosphate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 95% |
In dichloromethane at 20℃; for 1h; | 70% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 0.25h; | 100% |
In tetrahydrofuran at 20℃; for 3h; Schlenk technique; Inert atmosphere; | 77% |
In tetrahydrofuran |
4-nitro-aniline
Conditions | Yield |
---|---|
With Nitrogen dioxide In 1,4-dioxane at 10 - 40℃; | 100% |
With Nitrogen dioxide at 0℃; for 6h; | 92% |
With Nitrogen dioxide; N,N-dimethyl-formamide In N,N-dimethyl-formamide for 0.0833333h; | 91% |
With tributyl phosphate-NO2 In various solvent(s) at 10 - 15℃; | 90% |
With polyethylene glycol - NO2 In various solvent(s) | 84% |
dichloromethylenedimethyliminium chloride
4-nitro-aniline
Conditions | Yield |
---|---|
at -20℃; for 1h; ball mill; | 100% |
4-chlorobenzaldehyde
4-nitro-aniline
(4-chlorobenzylidene)(4-nitrophenyl)amine
Conditions | Yield |
---|---|
for 36h; Ambient temperature; | 100% |
In neat (no solvent) at 20℃; for 72h; | 80% |
In ethanol for 2h; Reflux; | 76% |
p-Anisaldehyde dimethyl acetal
4-methoxy-aniline
4-nitro-aniline
(E)-N-(4-methoxybenzylidene)-4-nitroaniline
Conditions | Yield |
---|---|
In dichloromethane Condensation; Heating; | 100% |
Conditions | Yield |
---|---|
In dichloromethane Condensation; Heating; | 100% |
Conditions | Yield |
---|---|
In dichloromethane Condensation; Heating; | 100% |
bis(trichloromethyl) carbonate
tert-butyl 4-aminobenzoate
4-nitro-aniline
1-(4'-nitrophenyl)-3-(4''-tert-butylcarboxyphenyl)urea
Conditions | Yield |
---|---|
Stage #1: bis(trichloromethyl) carbonate; 4-nitro-aniline With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 0.833333h; Substitution; Stage #2: tert-butyl 4-aminobenzoate In tetrahydrofuran at 20℃; for 42h; Substitution; | 100% |
4-nitro-aniline
4-chloro-5-methoxy-2-methyl-2H-pyridazin-3-one
Conditions | Yield |
---|---|
With potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate In toluene at 120℃; for 7h; Substitution; Amination; | 100% |
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