Conditions | Yield |
---|---|
With nitric acid; Chloroacetic anhydride at 50℃; for 4h; | A 94% B 5% |
With dinitrogen pentoxide; H-faujasite zeolite F-712 In dichloromethane | A 77% B 15% |
With nitric acid at 50℃; for 3h; | A 71.5% B 28.5% |
Conditions | Yield |
---|---|
With succinic acid anhydride; nitric acid at 4℃; for 50h; Product distribution / selectivity; | A 85% B 8.2% |
With Perfluorooctanesulfonic acid; nitric acid; ytterbium(III) perfluorooctanesulfonate In hexane at 60℃; for 4h; | A 84% B 16% |
With Perfluorooctanesulfonic acid; nitric acid; ytterbium(III) perfluorooctanesulfonate In hexane at 60℃; for 4h; | A 80% B 18% |
toluene
A
1-methyl-4-nitrobenzene
B
2,4-dinitrotoluene
C
2,6-dinitrotoluene
Conditions | Yield |
---|---|
With succinic acid anhydride; nitric acid at 4℃; for 50h; Product distribution / selectivity; | A 7.9% B 85% C 6.3% |
With nitric acid; dichloroacetic anhydride In dichloromethane at 50℃; for 0.166667h; Time; |
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane for 10h; Reflux; | 63% |
toluene
A
1-methyl-4-nitrobenzene
B
1-methyl-2-nitrobenzene
C
2,4-dinitrotoluene
D
2,6-dinitrotoluene
Conditions | Yield |
---|---|
With trinitratooxovanadium(V) In dichloromethane for 0.1h; Ambient temperature; Further byproducts given; | A 41% B 35% C 19% D 3% |
With sulfuric acid; nitric acid at 20 - 90℃; Product distribution; Further Variations:; Temperatures; Reagents; Nitration; | |
With MoO3 upon silica gel; nitric acid In tetrachloromethane at 20℃; for 2.5h; Product distribution; Further Variations:; Reagents; | |
With sulfuric acid; nitric acid; acetic anhydride at 30℃; Product distribution; Further Variations:; Temperatures; Reagents; residence time; | |
Stage #1: toluene With nitric acid; acetic anhydride at 20℃; Stage #2: With nitric acid; acetic anhydride In water at 50℃; Reagent/catalyst; |
Conditions | Yield |
---|---|
Nitrierung; |
4-Amino-2,6-dinitrotoluene
2,6-dinitrotoluene
Conditions | Yield |
---|---|
With sulfuric acid Diazotization.man schuettet das Produkt in Alkohol; | |
With hydrogenchloride; hypophosphoric acid; sodium nitrite | |
(i) (diazotization), (ii) (reduction); Multistep reaction; | |
Behandlung des Diazoniumsulfats mit siedendem Alkohol.Diazotization; |
toluene
A
1-methyl-3-nitrobenzene
B
1-methyl-4-nitrobenzene
C
1-methyl-2-nitrobenzene
D
2,4-dinitrotoluene
E
2,6-dinitrotoluene
Conditions | Yield |
---|---|
With sulfur dioxide; dinitrogen pentoxide at -78 - -11℃; for 4h; Product distribution; other aromatic comp., var. nitration systems; | A 1 % Chromat. B 8 % Chromat. C 7 % Chromat. D 56 % Chromat. E 15 % Chromat. |
With claycop (montmorillonite clay impregnated with copper nitrate); nitric acid; acetic anhydride In tetrachloromethane at 25℃; for 4h; Product distribution; other reagents, solvent, time dependence of yields; |
2-aci-Nitro-6-nitro-toluol
2,6-dinitrotoluene
Conditions | Yield |
---|---|
With perchloric acid; sodium perchlorate at 15 - 80℃; Kinetics; |
2,6-dinitrotoluene
Conditions | Yield |
---|---|
With sodium perchlorate; acetic acid at 15 - 80℃; Kinetics; other reaction partners; |
2,4,6-Trinitrotoluene
A
1,3,5-trinitrobenzene
B
2,6-dinitrotoluene
C
4,6-dinitrobenzo[c]isoxazole
D
2-amino-4,6-dinitrobenzoic acid
E
3, 5-dinitroaniline
Conditions | Yield |
---|---|
In benzene at 340℃; Product distribution; Kinetics; Rate constant; in sealed tube; other solvent (neat); other temp.; |
Conditions | Yield |
---|---|
in der Waerme bei groesserer Konzentration der Salpetersaeure entsteht zunaechst; |
sulfuric acid
nitric acid
toluene
A
2,4-dinitrotoluene
B
2,6-dinitrotoluene
Conditions | Yield |
---|---|
in der Waerme entsteht zunaechst; |
2,6-dinitrotoluene
Conditions | Yield |
---|---|
beim Schmelzen; |
1-methyl-2-nitrobenzene
sulfuric acid
water
nitric acid
A
2,4-dinitrotoluene
B
2,6-dinitrotoluene
Conditions | Yield |
---|---|
at 40 - 70℃; Product distribution; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ammonium sulfhydrate; alcohol 2: Behandlung des Diazoniumsulfats mit siedendem Alkohol.Diazotization View Scheme | |
Multi-step reaction with 2 steps 1: alcohol; NH4SH / man dampft zur Trochne ein, extrahiert mit siedender Salzsaeure, faellt mit Ammoniak, und krystallisiert es aus 40prozentiger Essigsaeure um 2: Behandlung des Diazoniumsulfats mit siedendem Alkohol.Diazotization View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HNO3-H2SO4-H2O mixtures / 20 °C 2: Nitrierung View Scheme |
toluene
A
2,4,6-Trinitrotoluene
B
2,4-dinitrotoluene
C
2,6-dinitrotoluene
Conditions | Yield |
---|---|
Stage #1: toluene With sulfuric acid; nitric acid at 45 - 55℃; Stage #2: With sulfuric acid; nitric acid at 60 - 80℃; |
toluene
A
1-methyl-3-nitrobenzene
B
1-methyl-2-nitrobenzene
C
2,4-dinitrotoluene
D
2,6-dinitrotoluene
Conditions | Yield |
---|---|
With sodium nitrate; sulfuric acid; nitric acid In water at 50℃; for 0.25h; Title compound not separated from byproducts.; |
1-methyl-2-nitrobenzene
A
2,4,6-Trinitrotoluene
B
2,4-dinitrotoluene
C
2,6-dinitrotoluene
Conditions | Yield |
---|---|
With ethylene glycol dinitrate In sulfuric acid at 0 - 20℃; Product distribution; Further Variations:; Reagents; |
toluene
A
2,4-dinitrotoluene
B
3,5-dinitrotoluene
C
2,6-dinitrotoluene
D
3,4-Dinitrotoluene
E
2,5-dinitrotoluene
Conditions | Yield |
---|---|
With ferric nitrate pentahydrate; nitric acid at 100℃; for 99h; |
toluene
A
2,4-dinitrotoluene
B
2,6-dinitrotoluene
C
2,5-dinitrotoluene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: nitric acid; chromium(III) nitrate hexahydrate / water / 5 h / 100 °C 2: nitric acid; ferric nitrate pentahydrate / 9 h / 100 °C View Scheme | |
Multi-step reaction with 2 steps 1: nitric acid; ferric nitrate pentahydrate / 0.25 h / 100 °C 2: nitric acid; ferric nitrate pentahydrate / 9 h / 100 °C View Scheme |
1-methyl-2-nitrobenzene
A
2,4-dinitrotoluene
B
2,6-dinitrotoluene
C
2,5-dinitrotoluene
Conditions | Yield |
---|---|
With ferric nitrate pentahydrate; nitric acid at 100℃; for 9h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With hydrogen In methanol at 50℃; under 1500.15 Torr; for 0.666667h; Inert atmosphere; | 100% |
With Fe3O4Rh; hydrazine hydrate In ethanol at 80℃; for 2h; Inert atmosphere; | 99% |
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 1h; | 99% |
Conditions | Yield |
---|---|
With lithium hydroxide In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; | 100% |
2,6-dinitrotoluene
N,N-dimethyl-formamide dimethyl acetal
3-nitro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 4h; Heating; | 100% |
In N,N-dimethyl-formamide at 115℃; for 6h; | 96% |
With copper(l) iodide; N,N-dimethyl-formamide at 180℃; under 6000.6 - 7500.75 Torr; for 0.166667h; microwave irradiation; | 85% |
2,6-dinitrotoluene
5-bromo-2-methyl-1,3-dinitrobenzene
Conditions | Yield |
---|---|
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid at 20℃; for 1h; | 100% |
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid at 20℃; for 1h; | 92% |
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid at 20℃; for 15h; Reagent/catalyst; | 92% |
Conditions | Yield |
---|---|
With lithium hydroxide In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; | 99% |
Conditions | Yield |
---|---|
Stage #1: 2,6-dinitrotoluene In 1,4-dioxane; water at 50℃; for 0.0833333h; Stage #2: With formic acid In 1,4-dioxane; water at 50℃; for 2h; Sealed tube; | 95% |
With ammonium sulfide In ethanol at 79℃; for 2h; Reflux; | 79% |
With formic acid; triethylamine; palladium on activated charcoal at 100℃; for 0.333333h; | 76% |
Conditions | Yield |
---|---|
With potassium hydroxide at 20℃; Addition; | 95% |
With tetraethylammonium tosylate In N,N-dimethyl-formamide for 0.833333h; Ambient temperature; 3.3 mAcm-2; | 94% |
With potassium tert-butylate In dimethyl sulfoxide; tert-butyl alcohol r.t., 5min. then 70-75 degC, 10min.; | 77% |
2,6-dinitrotoluene
2,6-dinitrobenzaldehyde
1,2-bis(2,6-dinitrophenyl)ethylene
Conditions | Yield |
---|---|
With piperidine In toluene Reflux; | 93% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 9h; Heating; | 91% |
Conditions | Yield |
---|---|
With caesium carbonate; potassium hydroxide In tetrahydrofuran at 70℃; for 12h; Inert atmosphere; Green chemistry; | 91% |
2,6-dinitrotoluene
N,N-dimethyl-formamide dimethyl acetal
A
3-nitro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene
B
(2,6-dinitrophenyl)acetaldehyde
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 9h; Heating; | A 90.9% B 2.2% |
Conditions | Yield |
---|---|
With caesium carbonate In methanol Addition; Heating; | 88% |
2,6-dinitrotoluene
oxalic acid diethyl ester
ethyl 3-(2,6-dinitrophenyl)pyruvate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide | 85% |
With sodium ethanolate In ethanol at 40℃; for 2h; | 20% |
With sodium ethanolate In ethanol at 40℃; for 4h; |
2,6-dinitrotoluene
N,N-dimethyl-formamide
3-nitro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene
Conditions | Yield |
---|---|
With propionic acid at 105℃; for 2h; | 84% |
Conditions | Yield |
---|---|
With carbon monoxide; hydrogen sulfide; iron(III) oxide at 325℃; for 1.05h; Product distribution; Mechanism; var. time; | A 80.2% B 4.5% C n/a |
2,6-dinitrotoluene
2-(bromomethyl)-1,3-dinitrobenzene
Conditions | Yield |
---|---|
With Perbenzoic acid; bromine In tetrachloromethane Heating; Irradiation; | 79% |
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 48h; Inert atmosphere; Reflux; | 35% |
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 100℃; for 13h; Inert atmosphere; | 29% |
2,6-dinitrotoluene
tributylphenylstannane
2′-methyl-1,1′:3′,1′′-terphenyl
Conditions | Yield |
---|---|
With bis(acetylacetonato)palladium(II); 18-crown-6 ether; potassium phosphate tribasic trihydrate; XPhos at 140℃; for 24h; Inert atmosphere; | 78% |
2,6-dinitrotoluene
5-chloro-2-methyl-1,3-dinitro-benzene
Conditions | Yield |
---|---|
With trichloroisocyanuric acid; sulfuric acid at 130℃; for 2h; | 74% |
With trichloroisocyanuric acid; sulfuric acid at 130℃; for 4h; | 73.6% |
With trichloroisocyanuric acid; sulfuric acid at 130℃; for 4h; | 73.6% |
Conditions | Yield |
---|---|
With caesium carbonate In tetrahydrofuran at 65℃; for 12h; Inert atmosphere; | 74% |
With caesium carbonate In tetrahydrofuran at 65℃; for 12h; Inert atmosphere; Green chemistry; | 74% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; Condensation; | 72% |
2,6-dinitrotoluene
Methyl thioglycolate
methyl ((2-methyl-3-nitrophenyl)thio)acetate
Conditions | Yield |
---|---|
With lithium hydroxide In N,N,N,N,N,N-hexamethylphosphoric triamide for 24h; Ambient temperature; | 70% |
Conditions | Yield |
---|---|
With (S)-2-(((tert-butyldimethylsilyl)oxy)diphenylmethyl)pyrrolidine; dmap In acetonitrile at 40℃; for 48h; enantioselective reaction; | 70% |
Conditions | Yield |
---|---|
With caesium carbonate In tetrahydrofuran at 65℃; for 12h; Inert atmosphere; | 66% |
With caesium carbonate In tetrahydrofuran at 65℃; for 12h; Inert atmosphere; Green chemistry; | 66% |
Conditions | Yield |
---|---|
With sodium chloride; paraformaldehyde; SiO2 In dimethyl sulfoxide; ethyl acetate; Petroleum ether; tert-butyl alcohol | 64% |
2,6-dinitrotoluene
p-(15NO2)-2,4,6-trinitrotoluene
Conditions | Yield |
---|---|
With nitrous acid; sulfuric acid at 90 - 100℃; for 2h; | 59% |
Conditions | Yield |
---|---|
With sodium dichromate; sulfuric acid for 20h; Ambient temperature; | 58% |
With potassium permanganate; sodium hydrogencarbonate In water for 5h; Oxidation; Heating; | 19% |
With water; nitric acid at 125 - 130℃; im Druckrohr; |
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