Conditions | Yield |
---|---|
With (NH4)2Ce(NO3)6 on Ca-bentonite In chloroform at 25℃; for 48h; | 98.5% |
With toluene-4-sulfonic acid; nickel(II) nitrate In acetone at 20℃; for 0.0166667h; | 98% |
With dimethylbromosulphonium bromide; tetrabutylammonium nitrite In acetonitrile at 20℃; for 1h; regioselective reaction; | 96% |
Conditions | Yield |
---|---|
With acetic anhydride In tetrachloromethane; nitric acid | 98% |
Conditions | Yield |
---|---|
With nitro acetate; silica gel In chloroform at -20 - 20℃; Nitration; | A 93% B 6% |
With copper(II) nitrate/zeolite H-Y for 0.0166667h; Product distribution; Further Variations:; heating mode; times; microwave irradiation; | A 88% B n/a |
With tert.-butylnitrite In acetonitrile at 29.84℃; Kinetics; Solvent; Temperature; | A 85% B n/a |
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at -5 - 25℃; | 93% |
Conditions | Yield |
---|---|
With Yb-Mo-modified montmorillonite HKSF; nitric acid In tetrahydrofuran at 20℃; for 12h; | A 88% B 3% |
With Montmorillonite KSF; nitric acid; hafnium oxychloride In tetrahydrofuran at 20℃; for 16h; | A 81% B 6% |
With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide at 20℃; for 6h; Ionic liquid; | A 78% B 16% |
4-methyl-2-nitrophenol
Conditions | Yield |
---|---|
With GLUTATHIONE In aq. phosphate buffer; acetonitrile at 37℃; for 4h; pH=7.4; Kinetics; | 88% |
(E)-methyl 3-(4-fluorophenyl)-2-((4-methyl-2-nitrophenoxy)methyl)acrylate
4-methyl-2-nitrophenol
Conditions | Yield |
---|---|
With GLUTATHIONE In aq. phosphate buffer; acetonitrile at 37℃; for 4h; pH=7.4; Kinetics; | 84% |
Conditions | Yield |
---|---|
With water In tetrahydrofuran at 25℃; for 2.5h; Schlenk technique; | 82% |
(E)-methyl 3-(4-methoxyphenyl)-2-((4-methyl-2-nitrophenoxy)methyl)acrylate
4-methyl-2-nitrophenol
Conditions | Yield |
---|---|
With GLUTATHIONE In aq. phosphate buffer; acetonitrile at 37℃; for 4h; pH=7.4; Kinetics; | 79% |
4-methyl-2-nitrophenol
Conditions | Yield |
---|---|
With GLUTATHIONE In aq. phosphate buffer; acetonitrile at 37℃; for 4h; pH=7.4; Kinetics; | 79% |
(E)-methyl 2-((4-methyl-2-nitrophenoxy)methyl)-3-phenylacrylate
4-methyl-2-nitrophenol
Conditions | Yield |
---|---|
With GLUTATHIONE In aq. phosphate buffer; acetonitrile at 37℃; for 4h; pH=7.4; Kinetics; | 78% |
p-cresol
B
4-methyl-2-nitrophenol
C
2-(2-hydroxy-5-methyl-3-nitrophenyl)-4-methyl-6-nitrophenol
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 12h; | A 10% B 77% C 12% |
4-Methylanisole
A
p-cresol
B
4-methyl-2-nitrophenol
C
4-methoxy-3-nitrotoluene
Conditions | Yield |
---|---|
With nitric acid In sulfuric acid at 25℃; | A 7.3% B 28.4% C 73% |
With nitric acid In sulfuric acid at 25℃; | A 8.25% B 32.5% C 67.8% |
With nitric acid In sulfuric acid at 25℃; | A 8.2% B 32.5% C 67.8% |
With nitric acid In sulfuric acid at 25℃; Rate constant; Product distribution; various acid concentrations and molar ratios; | A 8.1% B 31.2% C 64.5% |
4-methyl-2-nitrophenol
Conditions | Yield |
---|---|
With GLUTATHIONE In aq. phosphate buffer; acetonitrile at 37℃; for 4h; pH=7.4; Kinetics; | 73% |
p-cresol
nitro acetate
A
4-methyl-2-nitrophenol
B
4-methyl-4-nitrocyclohexa-2,5-dien-1-one
Conditions | Yield |
---|---|
In acetic anhydride at 22℃; Mechanism; NMR-investigation, also with AcO(15)NO2; | A 70% B n/a |
Conditions | Yield |
---|---|
With nitric acid In sulfuric acid at 25℃; Product distribution; various acid concentration; | A 8.1% B 31.2% C 68.8% |
4-Methylanisole
A
4-methyl-2-nitrophenol
B
4-methoxy-3-nitrotoluene
C
2,6-dinitro-p-cresol
Conditions | Yield |
---|---|
With dinitrogen tetraoxide In dichloromethane at -30℃; for 1h; Nitration; demethylation; | A 11% B 61% C 24% |
With tetranitromethane; tetrabutylammonium perchlorate In acetonitrile at 25 - 30℃; for 6h; Irradiation; Title compound not separated from byproducts; | A 6 % Spectr. B 55 % Spectr. C 39 % Spectr. |
p-cresol
A
4-methyl-2-nitrophenol
B
2,6-dinitro-p-cresol
C
4-methyl-4-nitrocyclohexa-2,5-dien-1-one
Conditions | Yield |
---|---|
With Nitrogen dioxide In dichloromethane at -23℃; for 1h; | A 8% B 60% C 32% |
Conditions | Yield |
---|---|
With air; nitrogen(II) oxide In acetonitrile for 2h; Ambient temperature; | A 16% B 58% |
With nitric acid; hydrazine at 25℃; Rate constant; | A 42% B 49% |
With tetranitromethane; tetrabutylammonium perchlorate In dichloromethane at 25 - 30℃; for 6h; Irradiation; Title compound not separated from byproducts; | A 39 % Spectr. B 61 % Spectr. |
With nitric acid; acetic acid |
para-chlorotoluene
A
4-methyl-2-nitrophenol
B
4-chloro-2-nitrotoluene
C
1-chloro-4-methyl-2-nitro-benzene
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid In water at 25℃; for 3.83333h; | A 9.3% B 39.1% C 31% |
With sulfuric acid; nitric acid In water at 25℃; for 3.83333h; Title compound not separated from byproducts; | A 9.3 % Chromat. B 39.1 % Chromat. C 31.0 % Chromat. |
Conditions | Yield |
---|---|
With bromine; silver nitrate In acetonitrile for 2h; Ambient temperature; | A 23% B 39% |
Conditions | Yield |
---|---|
With iodine; silver nitrate In acetonitrile for 2h; Ambient temperature; | A 25% B 37% |
p-cresol
A
4-methyl resorcinol
B
4-methyl-2-nitrophenol
C
4-methyl-1,2-dihydroxybenzene
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; dihydrogen peroxide; sodium dodecyl-sulfate In acetic acid for 48h; Ambient temperature; | A 22% B 12% C 30% |
4-methyl-2-nitrophenol
Conditions | Yield |
---|---|
With polymer-supported thiourea In acetone at 21℃; for 24h; Molecular sieve; Inert atmosphere; | 14% |
piperidine
(4-methyl-2-nitro-phenyl)-(2-nitro-phenyl)-ether
A
1-(2-nitrophenyl)piperidine
B
4-methyl-2-nitrophenol
piperidine
(2,4-dinitro-phenyl)-(4-methyl-2-nitro-phenyl)-ether
A
4-methyl-2-nitrophenol
B
1-(2,4-dinitrophenyl)piperidine
pyridine
p-cresol
diethyl ether
ethanol
hexanitroethane
4-methyl-2-nitrophenol
Conditions | Yield |
---|---|
at 0℃; |
Conditions | Yield |
---|---|
unter vermindertem Druck; |
Conditions | Yield |
---|---|
With pyridine; ethanol at 0℃; |
Conditions | Yield |
---|---|
With pyridine; ethanol |
Conditions | Yield |
---|---|
With hydrogen; palladium 10% on activated carbon In methanol at 23℃; for 5h; | 100% |
Stage #1: 4-methyl-2-nitrophenol With sodium dithionite In aq. phosphate buffer; acetone at 37℃; for 0.5h; pH=7.4; Stage #2: With disodium hydrogenphosphate; sodium dihydrogenphosphate | 95% |
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 16h; Inert atmosphere; | 93% |
4-methyl-2-nitrophenol
2-bromoethanol
2-(4-methyl-2-nitro-phenoxy)-ethanol
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 6h; Heating / reflux; | 100% |
trifluoromethylsulfonic anhydride
4-methyl-2-nitrophenol
trifluoromethanesulfonic acid 4-methyl-2-nitrophenyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 0.5h; | 100% |
With triethylamine In dichloromethane at 0℃; for 2h; |
4-methyl-2-nitrophenol
2-bromo-4-methyl-6-nitrophenol
Conditions | Yield |
---|---|
With benzyltrimethylammonium tribromide; calcium carbonate In methanol; dichloromethane | 99% |
With bromine; acetic acid | 95% |
With aluminium trichloride; bromine In dichloromethane at 20℃; | 91% |
Conditions | Yield |
---|---|
With Zn(N4,N4'-di(pyridin-4-yl)biphenyl-4,4'-dicarboxamide)(5-aminoisophthalate) In dichloromethane at 20℃; for 8h; | 99% |
With bismuth oxide perchlorate at 20℃; for 1h; | 82% |
With magnesium(II) perchlorate at 80℃; for 0.5h; | 70% |
4-methyl-2-nitrophenol
methyl (Z)-2-(bromomethyl)-3-(4-nitrophenyl)-2-propenoate
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; | 98% |
4-methyl-2-nitrophenol
(Z)-methyl 2-(bromomethyl)-3-phenylacrylate
(E)-methyl 2-((4-methyl-2-nitrophenoxy)methyl)-3-phenylacrylate
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; Inert atmosphere; | 97% |
With potassium carbonate In acetonitrile at 20℃; for 1h; | 95% |
Conditions | Yield |
---|---|
With Nitrogen dioxide In dichloromethane at -23℃; for 1h; | 96% |
formaldehyd
4-methyl-2-nitrophenol
6-bromomethyl-4-methyl-2-nitrophenol
Conditions | Yield |
---|---|
With hydrogen bromide; acetic anhydride; acetic acid at 80℃; for 24h; | 96% |
Cyclohexyl isocyanide
4-methyl-2-nitrophenol
propionaldehyde
4-chlorobenzylamine
Conditions | Yield |
---|---|
In methanol at 60℃; for 72h; | 96% |
In methanol at 60℃; Ugi-Smiles coupling; | 96% |
methyl (Z)-4-(bromomethyl)-3-(4-fluorophenyl)-2-propenoate
4-methyl-2-nitrophenol
(E)-methyl 3-(4-fluorophenyl)-2-((4-methyl-2-nitrophenoxy)methyl)acrylate
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; Inert atmosphere; | 96% |
With potassium carbonate In acetonitrile at 20℃; for 1h; | 90% |
4-methyl-2-nitrophenol
methyl (2Z)-2-(bromomethyl)-3-(4-methoxyphenyl)prop-2-enoate
(E)-methyl 3-(4-methoxyphenyl)-2-((4-methyl-2-nitrophenoxy)methyl)acrylate
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; Inert atmosphere; | 96% |
With potassium carbonate In acetonitrile at 20℃; for 1h; | 92% |
4-methyl-2-nitrophenol
1-Bromo-2-chloroethane
1-(2-chloro-ethoxy)-4-methyl-2-nitro-benzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 5h; | 96% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; |
Conditions | Yield |
---|---|
With Au NCs/TiO2 In toluene at 130℃; for 24h; Inert atmosphere; | 96% |
With triscarbonyl‐(η4–3,4‐bis(4‐methoxyphenyl)‐2,5‐diphenylcyclopenta‐2,4‐dienone)iron; trimethylamine-N-oxide In o-xylene at 150℃; for 24h; Solvent; Sealed tube; Inert atmosphere; | 89% |
With 1,1'-bis-(diphenylphosphino)ferrocene In toluene at 150℃; for 24h; Inert atmosphere; | 79% |
4-methyl-2-nitrophenol
2-iodo-4-methyl-6-nitrophenol
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; N,N,N-trimethylbenzenemethanaminium dichloroiodate In methanol; dichloromethane for 6h; Ambient temperature; | 95% |
With iodine; sodium hydrogencarbonate In water at 95℃; for 2.5h; | 88% |
With Iodine monochloride; acetic acid |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; | 95% |
With pyridine | |
With pyridine at 20℃; for 4h; |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 95% |
4-methyl-2-nitrophenol
methyl (2Z)-2-(bromomethyl)-3-(2-chlorophenyl)prop-2-enoate
C18H16ClNO5
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 20℃; for 1h; | 93% |
4-methyl-2-nitrophenol
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; Inert atmosphere; | 93% |
4-methyl-2-nitrophenol
benzyl bromide
1-(benzyloxy)-4-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; | 93% |
4-bromoethylbutanoate
4-methyl-2-nitrophenol
4-(4-methyl-2-nitrophenoxy)butyric acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 24h; Heating; | 92.3% |
4-methyl-2-nitrophenol
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; Inert atmosphere; | 92% |
1-bromo-octane
4-methyl-2-nitrophenol
4-methyl-2-nitro-1-octyloxybenzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide; acetone at 90℃; for 72h; | 91% |
4-methyl-2-nitrophenol
methyl (2Z)-2-(bromomethyl)-3-(4-methylphenyl)prop-2-enoate
C19H19NO5
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 20℃; for 1h; | 91% |
4-methyl-2-nitrophenol
methyl (2Z)-2-(bromomethyl)-3-(4-chlorophenyl)prop-2-enoate
C18H16ClNO5
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 20℃; for 1h; | 91% |
1. | orl-rat LD50:3360 mg/kg | HURC** Huntingdon Research Center Reports .(Brooklandville, MD.: )1972. |
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