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English name: 2-Nitrotoluene Synonyms:2-Methyl-1-nitrobenzene; 2-Methylnitrobenzene; o-Nitrophenylmethane; 2-Nitrotoluol; alpha-Methylnitrobenz… CAS No. 88-72-2 1.We have been specializing in special fine chemical for long, with strong
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inquirysuperior quality Appearance:light yellow to darker yellow-green liquid Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:1kg/bag, 1kg/drum or 25kg/drum or as per your request. Application:As the intermediate of dyes
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inquiryCAS:88-72-2 EINECS:201-853-3 MW:137.14 MF:C7H7NO2 Melting point:-9 °C Boiling point:225 °C(lit.) Appearance:yellow liquid Package:200kg/Steel drum Transportation:by sea Port:Shanghai
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Cas:88-72-2
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Conditions | Yield |
---|---|
copper(I) oxide In acetonitrile at 50℃; | 100% |
With [Rh(OH)(cod)]2; 1,3-bis-(diphenylphosphino)propane; water; sodium hydroxide In tetrahydrofuran at 90℃; for 24h; Inert atmosphere; | 81% |
With potassium carbonate In chloroform at 20℃; for 24h; Irradiation; Inert atmosphere; | 75% |
With copper diacetate; triethylamine at 35℃; for 21h; Sealed tube; | 26 %Spectr. |
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / Inert atmosphere 1.2: 2 h / 110 °C / Inert atmosphere 2.1: sodium acetate / 22 h / 35 °C / Sealed tube View Scheme |
Benzoic acid (1R,6R)-5-methyl-6-nitro-cyclohex-3-enyl ester
1-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
With potassium tert-butylate In benzene | 95% |
2-nitrophenylmethyl bromide
A
2,2'-dinitrobibenzyl
B
1-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate In acetonitrile controlled-potential electrolysis; further solvent - DMFA.; | A 95% B 2% |
With diisopropyl phosphite; sodium hydride In tetrahydrofuran for 3h; Ambient temperature; | A 86% B 4% |
With (C2H5)NClO4 In acetonitrile Mechanism; Rate constant; Product distribution; electrolysis; | |
With N-ethyl-N,N-diisopropylamine In dichloromethane for 5h; Inert atmosphere; Irradiation; | A 73 %Spectr. B 14 %Spectr. |
2-Methylphenylboronic acid
1-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
With N-Bromosuccinimide; [bis(trifluoroacetoxy)iodo]benzene; sodium nitrite In acetonitrile at 20℃; for 3h; regioselective reaction; | 90% |
With bismuth (III) nitrate pentahydrate In toluene at 70 - 80℃; for 2h; Inert atmosphere; | 90% |
With 1,1,1,3',3',3'-hexafluoro-propanol; N–nitrosaccharin at 60℃; for 19h; Reagent/catalyst; Inert atmosphere; Schlenk technique; | 82% |
Conditions | Yield |
---|---|
With sulfolane; sodium hydrogencarbonate at 200℃; for 2h; | 90% |
Conditions | Yield |
---|---|
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 4h; | A 88% B 12% |
With sodium nitrite for 0.0166667h; Reagent/catalyst; Microwave irradiation; | A 82% B 15% |
With bismuth(III) nitrate In tetrachloromethane | A 80% B n/a |
Conditions | Yield |
---|---|
With nitric acid In neat (no solvent) at 90℃; for 4h; regioselective reaction; | A 9 %Chromat. B 88% |
With nitric acid In hexane at 90℃; for 4h; regioselective reaction; | A 63.5 %Chromat. B 36.4 %Chromat. |
toluene
A
1-methyl-4-nitrobenzene
B
1-methyl-2-nitrobenzene
C
benzoic acid
Conditions | Yield |
---|---|
With methanesulfonic acid; 1-butyl-3-methylimidazolium nitrate In water for 48h; Heating / reflux; | A n/a B n/a C 85% |
With nitric acid; 1-butyl-3-methylimidazolium nitrate In water for 48h; Heating / reflux; | A n/a B n/a C 85% |
With nitric acid; 1-n-butyl-3-methylimidazolium methanesulfonate In water for 48h; Heating / reflux; | A n/a B n/a C 70% |
With nitric acid; 1-n-butyl-3-methylimidazolium methanesulfonate In water for 48h; Heating / reflux; | A n/a B n/a C 70% |
Conditions | Yield |
---|---|
palladium diacetate In tetrahydrofuran at 40℃; for 3h; | 85% |
tetramethylstannane
2-Nitrobenzenediazonium Bisulfate
1-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
palladium diacetate In water; acetonitrile at 20℃; for 2h; | 84% |
With palladium diacetate In water; acetonitrile at 20℃; for 2h; | 72% |
(S)-(o-nitrobenzyl)-6-thioguanine
A
1-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
With hydrogen; platinum(IV) oxide In ethanol under 1551.4 Torr; for 24h; Product distribution; effect of presence of morpholine; | A n/a B 80% |
toluene
A
1-methyl-3-nitrobenzene
B
1-methyl-4-nitrobenzene
C
1-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
With copper(II) nitrate on K10 montmorillonite; acetic anhydride In tetrachloromethane for 120h; Ambient temperature; | A 1% B 79% C 20% |
With nitric acid In trifluoroacetic acid at 25℃; Rate constant; | A 0.7% B 66.7% C 32.6% |
With ortho-methylphenyl iodide; potassium nitrate In trifluoroacetic acid for 0.5h; Product distribution; nitration of aromatic compounds in the presence of aryl iodides; other temperatures, other reagents; | A n/a B 64% C 33% |
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene
methyl iodide
1-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
With C21H30ClNPPd; potassium tert-butylate In tert-Amyl alcohol at 65℃; for 18h; Sealed tube; Inert atmosphere; Glovebox; | 78% |
Diethyl 2-(2-nitrophenyl)propanedioate
1-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
With magnesium chloride In N,N-dimethyl acetamide at 140 - 150℃; for 24h; Decarboxylation; Krapcho's reaction; | 77% |
diisopropyl hydrogenphosphonate
2-nitrophenylmethyl bromide
A
2,2'-dinitrobibenzyl
B
1-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
With sodium hydride In isopropyl alcohol for 3h; Ambient temperature; | A 74% B 18% C 6% |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 70℃; for 2h; | 70% |
With nitramide; sulfuric acid In water at -15 - -2℃; for 2.25h; | 18% |
With sulfuric acid; nitric acid at 20℃; |
trimethyl(2-nitrobenzyl)silane
benzaldehyde
A
1-methyl-2-nitrobenzene
B
α-phenyl-2-nitrophenethyl alcohol
Conditions | Yield |
---|---|
With hydrogenchloride; potassium fluoride; 18-crown-6 or silica-supported tetrabutylammonium fluoride In tetrahydrofuran at 20℃; for 12h; Yields of byproduct given; | A n/a B 70% |
2-iodo-6-nitrotoluene
1-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
With palladium diacetate; caesium carbonate; triphenylphosphine; benzyl alcohol In 1,2-dimethoxyethane at 90℃; Inert atmosphere; | 70% |
toluene
A
1-methyl-3-nitrobenzene
B
1-methyl-4-nitrobenzene
C
1-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
Product distribution; Ambient temperature; | A 3% B 32% C 65% |
trimethyl(2-nitrobenzyl)silane
benzyl bromide
A
1-methyl-2-nitrobenzene
B
1-nitro-2-phenethylbenzene
Conditions | Yield |
---|---|
With hydrogenchloride; potassium fluoride; 18-crown-6 or silica-supported tetrabutylammonium fluoride In tetrahydrofuran at 20℃; for 12h; Yields of byproduct given; | A n/a B 60% |
Conditions | Yield |
---|---|
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane for 3h; Heating; | 60% |
2-iodo-6-nitrotoluene
A
1-methyl-2-nitrobenzene
B
2,2'-dimethyl-3,3'-dinitrobiphenyl
Conditions | Yield |
---|---|
With copper In N,N-dimethyl-formamide at 190℃; for 24h; | A n/a B 53% |
toluene
A
1-methyl-4-nitrobenzene
B
1-methyl-2-nitrobenzene
C
2,4-dinitrotoluene
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 20℃; for 0.00416667h; | A 37.8% B 52.2% C 4.3% |
With di-tert-butyl dicarbonate; nitric acid at 4℃; for 50h; Product distribution / selectivity; | A 47% B 45% C 5.5% |
With butanoic acid anhydride; nitric acid at 50℃; for 4h; |
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate In acetonitrile preparative electrolyse, - 0.89 V; | A 52% B n/a C 18% |
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate In acetonitrile at 20℃; Rate constant; electrolyse, -0.89 V; | A 52% B 18% |
2-bromo-6-nitrotoluene
1-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
With 0.60mol% Pd/C; hydrogen; sodium hydrogencarbonate In methanol at 20℃; for 0.583333h; regioselective reaction; | 52% |
2-(2-nitrophenyl)acetic acid
A
1-methyl-2-nitrobenzene
B
2-nitro-benzaldehyde
Conditions | Yield |
---|---|
With oxygen; copper diacetate In dimethyl sulfoxide at 120℃; for 18h; Sealed tube; | A 52% B 46% |
potassium 2-(2-nitrophenyl)acetate
A
1-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); XPhos In diethylene glycol dimethyl ether at 140℃; for 2h; Inert atmosphere; | A n/a B 52% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; bromine In dichloromethane; water for 4h; Reflux; | 100% |
Stage #1: 1-methyl-2-nitrobenzene With 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane for 0.333333h; Stage #2: With hydrogen bromide; dihydrogen peroxide In 1,2-dichloro-ethane at 72 - 75℃; for 2h; Solvent; Temperature; | 98.5% |
With sodium hypochlorite; 2,2'-azobis(isobutyronitrile); hydrogen bromide In chlorobenzene at 85℃; for 7h; Temperature; Solvent; | 97% |
Conditions | Yield |
---|---|
With hydrogen; palladium In methanol at 25℃; under 2327.2 Torr; for 1.5h; | 100% |
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃; | 100% |
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃; under 760 Torr; Rate constant; | 100% |
1-methyl-2-nitrobenzene
N,N'-Di-o-tolyl-diazene N-oxide
Conditions | Yield |
---|---|
With bismuth for 1.5h; | 100% |
With sodium tetrahydroborate; water In ethanol at 30℃; for 6h; chemoselective reaction; | 92% |
With oxygen; ammonium chloride; zinc In [bmim][BF4]; water at 20℃; for 18h; | 88% |
Conditions | Yield |
---|---|
Stage #1: 1-methyl-2-nitrobenzene With ammonium formate; palladium on activated charcoal In methanol; water at 20℃; for 4.5h; Stage #2: propyl cyanide In methanol; water | 100% |
Conditions | Yield |
---|---|
Stage #1: 1-methyl-2-nitrobenzene With ammonium formate; palladium on activated charcoal In methanol; water at 20℃; Stage #2: propiononitrile In methanol; water | 100% |
1-methyl-2-nitrobenzene
oxalic acid diethyl ester
2-(2-nitrophenyl)acetic acid
Conditions | Yield |
---|---|
Stage #1: 1-methyl-2-nitrobenzene; oxalic acid diethyl ester With sodium In ethanol at 20 - 45℃; for 3h; Stage #2: With water In ethanol at 60℃; for 1h; Reagent/catalyst; | 99.8% |
Stage #1: 1-methyl-2-nitrobenzene; oxalic acid diethyl ester With sodium In ethanol at 45℃; for 3h; Stage #2: With water In ethanol at 60℃; for 1h; | 99.8% |
Conditions | Yield |
---|---|
With sodium hydroxide In water; dimethyl sulfoxide at 50℃; for 1h; Large scale reaction; | 99.5% |
64% | |
With potassium hydroxide In water; dimethyl sulfoxide at 0℃; for 5h; | 46% |
1-methyl-2-nitrobenzene
nitrobenzotrichloride
Conditions | Yield |
---|---|
With chlorine at 120℃; for 6h; Temperature; | 99.2% |
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol; water; 1,2-dichloro-ethane at 45℃; for 2h; Catalytic behavior; Temperature; | 99% |
With hydrazine hydrate In ethanol; dichloromethane at 0 - 2℃; for 6h; Solvent; Temperature; | 91.8% |
With sodium tetrahydroborate; palladium diacetate In ethanol; dichloromethane; water at 20℃; for 0.133333h; | 84% |
Conditions | Yield |
---|---|
Stage #1: 1-methyl-2-nitrobenzene With hydrogen In ethanol at 25℃; under 11172.7 Torr; Flow reactor; Stage #2: With hydrogenchloride In ethanol Flow reactor; chemoselective reaction; | 99% |
With hydrogenchloride; tin(ll) chloride In ethanol; water at 30℃; Rate constant; Mechanism; various concentration of HCl; different amounts of H2O as solvent; | |
Stage #1: 1-methyl-2-nitrobenzene With phosgene; sodium tetrahydroborate; copper(II) sulfate In methanol at 20℃; Stage #2: With hydrogenchloride In methanol; diethyl ether | 545 mg |
Conditions | Yield |
---|---|
With bis(acetylacetonato)palladium(II); potassium phosphate tribasic trihydrate; 2-(2,6-diethyl-4-methylphenyl)-5-(2,4,6-triisopropylphenyl)imidazo[1,5-a]pyridin-2-ium chloride In 1,4-dioxane at 130℃; for 24h; Inert atmosphere; | 99% |
1-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
Stage #1: 1-methyl-2-nitrobenzene With chlorosulfonic acid at 115℃; for 4h; Stage #2: With sodium carbonate In water at 20℃; | 98.6% |
1-methyl-2-nitrobenzene
N,N-dimethyl-formamide dimethyl acetal
trans-β-dimethylamino-2-nitrostyrene
Conditions | Yield |
---|---|
With copper(l) iodide; N,N-dimethyl-formamide at 180℃; under 6000.6 - 7500.75 Torr; for 2h; microwave irradiation; | 98% |
In N,N-dimethyl-formamide at 140℃; for 24h; | 88% |
In N,N-dimethyl-formamide for 26h; Heating; | 86% |
Conditions | Yield |
---|---|
With nitric acid; acetic anhydride at 50℃; for 4h; | 97% |
bei der Nitrierung; | |
With Nitroethane; boron trifluoride-dinitrogen tetraoxide |
2-Chloro-F-propane
1-methyl-2-nitrobenzene
heptafluoroisopropyl-3-methyl-4-nitrobenzene
Conditions | Yield |
---|---|
With hydrogen fluoride; antimony pentafluoride at 80℃; for 2h; Friedel-Crafts Alkylation; Autoclave; Industrial scale; | 97% |
Conditions | Yield |
---|---|
With hydrogen In toluene at 80℃; under 15001.5 Torr; for 18h; Autoclave; | 96% |
With formic acid; Au/TiO2-R In water at 80℃; under 760.051 Torr; for 9h; Inert atmosphere; Green chemistry; chemoselective reaction; | 91% |
With hydrogen In methanol at 20℃; under 760.051 Torr; for 6h; | 88% |
Conditions | Yield |
---|---|
With gold nano particles supported on rutile TiO2 In toluene at 70℃; under 750.075 Torr; for 3.5h; Inert atmosphere; chemoselective reaction; | 96% |
With palladium(II) trifluoroacetate; triphenylphosphine In water at 80℃; for 0.333333h; Sealed tube; Green chemistry; | 80% |
With palladium particles distributed over the surface of fibrous silica nanospheres modified via aminopropyltriethoxysilane In toluene at 70℃; for 3h; | 96 %Chromat. |
Conditions | Yield |
---|---|
With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate In methanol at 60℃; for 3h; Temperature; Solvent; | 95.9% |
methanol
1-methyl-2-nitrobenzene
phenol
4-phenylamino-3-methyl-1-methoxybenzene
Conditions | Yield |
---|---|
Stage #1: methanol; 1-methyl-2-nitrobenzene With 3 % platinum on carbon; hydrogen In water at 50℃; under 750.075 Torr; for 8h; Autoclave; Inert atmosphere; Stage #2: phenol With 3 % platinum on carbon In cyclohexanone at 250℃; under 7500.75 Torr; for 2h; Autoclave; Inert atmosphere; | 95.4% |
1-methyl-2-nitrobenzene
2,2'-dinitrobibenzyl
Conditions | Yield |
---|---|
Stage #1: 1-methyl-2-nitrobenzene With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.0333333h; Inert atmosphere; Stage #2: With bromine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; | 95% |
With 5-chloro-1-methyl-1H-pyrazole-4-carbaldehyde; potassium hydroxide In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere; | 88% |
With sodium; formic acid ethyl ester In hexane at 0 - 5℃; for 24h; | 70.4% |
Conditions | Yield |
---|---|
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h; Rate constant; pH 9; | 95% |
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h; | 95% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; sodium bromide at 40℃; for 12h; Temperature; | 94.2% |
1-methyl-2-nitrobenzene
N,N-dimethyl-formamide dimethyl acetal
N,N-dimethyl-2-(2-nitrophenyl)ethenylamine
Conditions | Yield |
---|---|
In chloroform; N,N-dimethyl-formamide at 175℃; under 11251.1 Torr; for 2h; Solvent; Temperature; Pressure; | 95% |
In N,N-dimethyl-formamide at 175℃; under 3750.38 Torr; for 2h; | 91% |
In N,N-dimethyl-formamide for 26h; Heating; | 86% |
Conditions | Yield |
---|---|
Stage #1: 1-methyl-2-nitrobenzene With sodium tetrahydroborate In water at 60 - 70℃; Green chemistry; Stage #2: acetic anhydride In water at 60 - 70℃; Green chemistry; | 95% |
Stage #1: 1-methyl-2-nitrobenzene In water for 0.0833333h; Stage #2: With sodium tetrahydroborate In water at 65℃; for 0.05h; Stage #3: acetic anhydride In water at 65℃; for 0.0333333h; Catalytic behavior; | 95% |
With sodium tetrahydroborate at 60℃; for 0.15h; | 93% |
With samarium; acetic acid In methanol at 20℃; for 1.5h; | 88% |
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 nickel-doped graphene carbon nitride nanoparticles; air In ethanol at 25℃; for 8h; Irradiation; Green chemistry; | 94% |
Stage #1: 1-methyl-2-nitrobenzene With bromine In propan-1-ol at 20℃; for 0.25h; UV-irradiation; Stage #2: With sodium hydrogencarbonate In propan-1-ol for 2h; Solvent; Reflux; UV-irradiation; | 89% |
With oxygen In acetonitrile at 20℃; for 12h; Irradiation; | 80% |
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