Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 16h; | 99.5% |
With pyridine In dichloromethane at 0 - 20℃; for 1h; | 97% |
In water at 80℃; for 0.0833333h; Microwave irradiation; Green chemistry; chemoselective reaction; | 96% |
Conditions | Yield |
---|---|
With sodium nitrate; sulfuric acid at 0 - 5℃; for 3h; | 99% |
With ammonium molybdate; water; nitric acid In chloroform for 6h; Nitration; Heating; | 99% |
With nitric acid; cetyltrimethylammonim bromide In acetonitrile at 24.84℃; for 2h; Micellar solution; regioselective reaction; | 85% |
p-nitroacetophenone oxime
N-(4-Nitrophenyl)acetamide
Conditions | Yield |
---|---|
With chlorosulfonic acid In toluene at 90℃; for 0.5h; Beckmann rearrangement; | 99% |
With trifluoromethylsulfonic anhydride In dichloromethane at 20℃; for 2h; Beckmann Rearrangement; Inert atmosphere; | 94% |
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In acetonitrile at 20℃; Beckmann Rearrangement; | 93% |
Conditions | Yield |
---|---|
With aluminum oxide at 25℃; for 0.666667h; | 98% |
With lanthanum(III) nitrate at 20℃; for 0.25h; | 98% |
In ethyl acetate at 20℃; for 20h; Inert atmosphere; | 98% |
N-(4-nitrophenyl)ethanethioamide
N-(4-Nitrophenyl)acetamide
Conditions | Yield |
---|---|
With bismuth(III) nitrate In acetonitrile for 0.166667h; Heating; | 98% |
With acidified wet silica gel; tetrabutylammonium periodite at 20℃; for 0.0333333h; Neat (no solvent); | 97% |
at 20℃; for 0.0833333h; Neat (no solvent); | 96% |
Conditions | Yield |
---|---|
Stage #1: 4-nitro-aniline; diethyl malonate at 100 - 130℃; Stage #2: With caesium carbonate In 1,4-dioxane at 100℃; | 98% |
Conditions | Yield |
---|---|
With manganese(III) acetate; ammonium thiocyanate at 25℃; for 2h; | 95% |
With Starbon-400-SO3H at 130℃; for 0.0333333h; Microwave irradiation; chemoselective reaction; | 92% |
With palladium (II) nanoparticles supported on Schiff-base modified clinoptilolite nanocatalyst In neat (no solvent) at 20℃; for 0.25h; Green chemistry; chemoselective reaction; | 92% |
4-nitroacetophenone oxime
N-(4-Nitrophenyl)acetamide
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran; ethyl acetate at 70℃; for 3h; Beckmann rearrangement; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With O-benzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid In water; acetonitrile at 23℃; for 24h; Inert atmosphere; | 92% |
With sodium azide; sulfuric acid; silica gel at 60℃; for 0.75h; Schmidt reaction; | 90% |
With formic acid; hydroxylamine hydrochloride; silica gel at 80℃; for 4h; Beckmann Rearrangement; | 90% |
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane for 10h; Reflux; | 92% |
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h; | 86% |
With water; fluorine In chloroform; acetonitrile at -15℃; for 0.0333333h; | 80% |
With sodium perborate In acetic acid at 50 - 60℃; for 2h; | 55% |
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In water; acetonitrile at 80℃; Microwave irradiation; | 88% |
With 2,6-dimethylpyridine In water at 80℃; for 0.166667h; Microwave irradiation; |
Conditions | Yield |
---|---|
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 4h; | A 14% B 86% |
With bismuth (III) nitrate pentahydrate; acetic anhydride In dichloromethane at 23℃; for 3h; Solvent; Temperature; Reagent/catalyst; regioselective reaction; | A 81% B n/a |
With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide at 20℃; for 6h; Ionic liquid; | A 22% B 71% |
p-nitroacetophenone oxime
A
N-(4-Nitrophenyl)acetamide
B
N-methyl-4-nitrobenzamide
Conditions | Yield |
---|---|
With silica gel; caesium carbonate; N-tosylimidazole In N,N-dimethyl-formamide for 2h; Beckmann rearrangement; Reflux; | A 86% B 8% |
Conditions | Yield |
---|---|
With [Zn(BH4)2(py)] In tetrahydrofuran for 5h; Heating; | 85% |
With aluminum (III) chloride; triethylamine at 25℃; for 0.333333h; | 74% |
Conditions | Yield |
---|---|
In acetic acid for 4.5h; Reflux; chemoselective reaction; | 85% |
Conditions | Yield |
---|---|
With sulphuric acid immobilized on silica gel In neat (no solvent) at 70℃; for 8h; Green chemistry; | 85% |
With Imidazole hydrochloride at 150℃; for 4h; Sealed tube; | 63% |
With potassium tert-butylate at 20℃; Sealed tube; Inert atmosphere; | 47% |
N-(4-Nitrophenyl)acetamide
Conditions | Yield |
---|---|
With trifluoroacetic acid for 8h; | 82% |
Conditions | Yield |
---|---|
With aluminium(III) iodide In acetonitrile for 0.416667h; Heating; | 80% |
Conditions | Yield |
---|---|
With copper(II)-grafted guanidine acetic acid-modified magnetite nanoparticles In water at 20℃; for 0.0833333h; Green chemistry; chemoselective reaction; | 80% |
With Fe3O4(at)Chit-TCT-Salen-Cu(II) In water at 20℃; for 0.0833333h; | 80% |
With copper(ll) sulfate pentahydrate In methanol at 20℃; for 0.0833333h; | 57% |
2,4,6-triacetyloxy-1,3,5-triazine
4-nitro-aniline
N-(4-Nitrophenyl)acetamide
Conditions | Yield |
---|---|
at 25℃; for 0.166667h; neat (no solvent); | 77% |
Conditions | Yield |
---|---|
With [Ru-NHC] In toluene at 110℃; for 8h; Inert atmosphere; Schlenk technique; Sealed tube; | 76% |
With sulfated tungstate In toluene for 24h; Reflux; Green chemistry; | 74% |
With C28H26ClN3ORuS In 1,4-dioxane at 100℃; for 8h; Sealed tube; Inert atmosphere; | 74% |
With 1-(3-sulfopropyl)pyridinium phosphotungstate In neat (no solvent) at 120℃; for 1.33333h; Microwave irradiation; | 56% |
Conditions | Yield |
---|---|
With chloroform; dimethyl sulfoxide at 120℃; for 24h; Green chemistry; | 75% |
With chloroform; copper(II) acetate monohydrate In dimethyl sulfoxide at 120℃; for 14h; Green chemistry; chemoselective reaction; | 73% |
N′-(4-nitrophenyl)-N-(1,7-dihydro-7-oxo-1,3-diphenylbenzo[e][1,2,4]triazin-6-yl)benzimidamide
acetic acid
A
N-(4-Nitrophenyl)acetamide
B
N-(1,7-dihydro-7-oxo-1,3-diphenylbenzo[e][1,2,4]triazin-6-yl)benzamide
C
8-(4-nitrophenyl)-1,3,7-triphenyl-4,8-dihydro-1H-imidazo[4,5-g][1,2,4]benzotriazin-4-yl
Conditions | Yield |
---|---|
at 120℃; for 1h; | A 33% B 70% C 13% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In water at 70℃; for 8h; Green chemistry; | 69% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium t-butanolate In toluene at 100℃; for 16h; | 50% |
acetic anhydride
1,2-bis(p-nitrophenylazo)cyclohexene
A
N-(4-Nitrophenyl)acetamide
B
4-acetoxy-2-(p-nitrophenyl)-4,5,6,7-terahydro-2H-benzo<1,2,3>triazole
C
N-(4-Nitro-phenyl)-N-[2-(4-nitro-phenyl)-4,5,6,7-tetrahydro-2H-benzotriazol-4-yl]-acetamide
Conditions | Yield |
---|---|
In acetic acid for 0.25h; Ambient temperature; | A 25% B 25% C 67% |
4-nitrophenyl azide
dimethylglyoxal
A
N-(4-Nitrophenyl)acetamide
B
4-nitro-aniline
Conditions | Yield |
---|---|
With Me4NPF4 In N,N-dimethyl-formamide Product distribution; Mechanism; electrolytic reduction at a Pt gauze electrode at a potential of -0.30 V; other supporting electrolytes; | A 37% B 67% |
(4-nitrophenyl)ethanone
A
p-nitroacetophenone oxime
B
N-(4-Nitrophenyl)acetamide
Conditions | Yield |
---|---|
With acetylhydroxamic acid; sulfuric acid In acetonitrile at 80℃; under 1292.9 Torr; for 0.25h; Microwave irradiation; | A 10% B 67% |
(4-nitrophenyl)ethanone
A
N-(4-Nitrophenyl)acetamide
B
N-methyl-4-nitrobenzamide
Conditions | Yield |
---|---|
With sodium hydrogen sulfate; hydroxylamine hydrochloride; silica gel for 0.0333333h; Heating; | A 18% B 62% |
With phosphorus pentaoxide; sodium azide; silica gel for 0.166667h; Schmidt reaction; microwave irradiation; |
Conditions | Yield |
---|---|
With copper bronze; tetrabutylammonium nitrate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 100℃; | 57% |
4-tert-butylacetanilide
A
N-(4-Nitrophenyl)acetamide
B
N-(4-(tert-butyl)-2-nitrophenyl)acetamide
Conditions | Yield |
---|---|
With nitric acid at 0℃; | A 10% B 56% |
Conditions | Yield |
---|---|
With hydrazine hydrate; nickel In methanol for 6h; | 100% |
With indium; acetic acid In tetrahydrofuran Heating; | 100% |
With trimethylamine-borane; palladium hydroxide - carbon In methanol for 3.5h; Heating; | 99% |
N-(4-Nitrophenyl)acetamide
Conditions | Yield |
---|---|
With Nitrogen dioxide at 5℃; | 100% |
N-(4-Nitrophenyl)acetamide
4-nitroaniline hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride In methanol for 0.1h; Reflux; | 99.8% |
Conditions | Yield |
---|---|
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; for 0.166667h; Green chemistry; | 99% |
With sodium periodate; sulfuric acid; sodium dodecyl-sulfate; acetic acid; sodium chloride In water at 25℃; for 2h; | 73% |
With chromium(VI) oxide; hydrogenchloride; acetic acid Ambient temperature; | 58% |
Conditions | Yield |
---|---|
Stage #1: N-(4-Nitrophenyl)acetamide With Decaborane; acetic acid; palladium on activated charcoal In methanol for 0.5h; Heating; Stage #2: 4-bromo-benzaldehyde With Decaborane In methanol at 20℃; for 0.5h; Stage #3: formaldehyd With Decaborane In methanol; water at 20℃; for 0.5h; | 99% |
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; Microwave irradiation; Green chemistry; | 99% |
N-(4-Nitrophenyl)acetamide
Conditions | Yield |
---|---|
With sodium hydride In toluene at 20℃; for 10h; Schlenk technique; Inert atmosphere; | 98% |
N-(4-Nitrophenyl)acetamide
N-(2,6-dichloro-4-nitrophenyl)acetamide
Conditions | Yield |
---|---|
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; for 0.583333h; Green chemistry; | 97.5% |
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 ammonium molybdate; water; nitric acid In chloroform for 6h; Nitration; Heating; | 97% |
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 3h; | 94% |
With sulfuric acid; nitric acid at 0℃; for 1h; |
formaldehyd
N-(4-Nitrophenyl)acetamide
butanone
(N-sec-butyl-N-methylamino)-4-acetamidoaniline
Conditions | Yield |
---|---|
Stage #1: N-(4-Nitrophenyl)acetamide; butanone With Decaborane; palladium on activated charcoal In methanol for 0.5h; Heating; Stage #2: With Decaborane In methanol at 20℃; for 2h; Stage #3: formaldehyd With Decaborane In methanol; water at 20℃; for 1.5h; | 95% |
N-(4-Nitrophenyl)acetamide
5-methyl-1-(4-nitrophenyl)-1H-tetrazole
Conditions | Yield |
---|---|
With picoline; diphenyl phosphoryl azide for 16h; Reagent/catalyst; Reflux; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With [Zn(BH4)2(py)] In tetrahydrofuran for 3.1h; Heating; | 94% |
With mineral acid durch elektrolytische Reduktion; | |
With hydrogenchloride; tin |
Di-tert-butyl acetylenedicarboxylate
N-(4-Nitrophenyl)acetamide
triphenylphosphine
Conditions | Yield |
---|---|
In ethyl acetate at 20℃; for 6h; | 94% |
N-(4-Nitrophenyl)acetamide
acetic anhydride
N,N'-diacetyl-1,4-phenylenediamine
Conditions | Yield |
---|---|
Stage #1: N-(4-Nitrophenyl)acetamide With sodium tetrahydroborate; water In neat (no solvent) at 20℃; for 0.0166667h; Stage #2: acetic anhydride In neat (no solvent) at 40℃; for 0.0666667h; Reagent/catalyst; | 94% |
N-(4-Nitrophenyl)acetamide
butanone
N-(4-(sec-butylamino)phenyl)acetamide
Conditions | Yield |
---|---|
With Decaborane; 10percent Pd/C In methanol for 2.5h; Reduction; Reductive amination; | 91% |
N-(4-Nitrophenyl)acetamide
dimethyl acetylenedicarboxylate
triphenylphosphine
Conditions | Yield |
---|---|
In ethyl acetate at 20℃; for 6h; | 91% |
N-(4-Nitrophenyl)acetamide
triphenylphosphine
acetylenedicarboxylic acid diethyl ester
Conditions | Yield |
---|---|
In ethyl acetate at 20℃; for 6h; | 91% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 50℃; for 3h; Friedel Crafts acylation; Inert atmosphere; | 91% |
With trifluorormethanesulfonic acid In dichloromethane at 50℃; for 3h; | 91% |
N-(4-Nitrophenyl)acetamide
sodium 4-methylbenzenesulfinate
N-(4-(4-methylphenylsulfonamido)phenyl)acetamide
Conditions | Yield |
---|---|
With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; sodium hydrogen sulfite; iron(II) chloride In dimethyl sulfoxide at 60℃; for 12h; Sealed tube; Inert atmosphere; | 90% |
MF: C8H8N2O3
MW: 180.16
EINECS: 203-169-0
mp: 213-215 °C(lit.)
storage temp: 2-8°C
Merck: 14,6581
BRN: 2211962
CAS DataBase Reference: 104-04-1(CAS DataBase Reference)
Synonyms:P-NITROACETANILIDE;N-ACETYL-4-NITROANILINE;LABOTEST-BB LT00455738;4'-NITROACETANILIDE;4-NITROACETANILIDE;ACETIC ACID 4-NITROANILIDE;1-Nitro-4-acetylaminobenzene;Acetamide, N-(4-nitrophenyl)-
The structure of p-NITROACETANILIDE(104-04-1) is:
Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 3
RTECS: AE5075000
Moderately toxic by intraperitoneal route. Reaction with sulfuric acid is vigorous with much gas evolution. When heated to decomposition it emits toxic fumes of NOx.
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