570-24-1

Basic information

• Product Name: 2-Methyl-6-nitroaniline
• Synonyms: 2-Methyl-6-nitroaniline,99%;2-Methyl-6-nitroaniline ,98%;2-Methyl-6-nitroaniline, 99% 25GR;1-Nitro-2-aMino-3-Methylbenzene;NSC 286;NSC 52218;2-Amino-1-methyl-3-nitrobenzene 3-Nitro-2-aminotoluene 6-Nitro-o-toluidine;2-Amino-3-methylnitrobenzene
• CAS NO: 570-24-1
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.15
• EINECS: 209-329-6
• Product Categories: Benzene derivates;API intermediates;Aromatics Compounds;Aromatics;Phenyls & Phenyl-Het;Miscellaneous Reagents;Building Blocks;C7;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Pharmaceutical intermediates;amine| nitro-compound;Intermediates of Dyes and Pigments;Anilines, Aromatic Amines and Nitro Compounds;Amines;Phenyls & Phenyl-Het
• Mol File: 570-24-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 93-96 °C(lit.)
• Boiling Point: 124 °C / 1mmHg
• Flash Point: 110 °C
• Appearance: Brownish/Crystalline Powder
• Density: 1.19 g/cm3
• Vapor Pressure: 0.0144mmHg at 25°C
• Refractive Index: 1.6276 (estimate)
• Storage Temp.: -20?C Freezer
• Solubility: <1mg/l
• PKA: -0.44±0.25(Predicted)
• Water Solubility: <0.1 g/100 mL at 23℃
• BRN: 1868029
• CAS DataBase Reference: 2-Methyl-6-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-6-nitroaniline(570-24-1)
• EPA Substance Registry System: 2-Methyl-6-nitroaniline(570-24-1)

Safety Data

• Hazard Codes: T,N,Xi
• Statements: 23/24/25-33-51/53
• Safety Statements: 28-36/37-45-61-28A
• RIDADR: UN 2660 6.1/PG 3
• WGK Germany: 3
• F: 10
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 570-24-1(Hazardous Substances Data)

Usage

Uses

2-Methyl-6-nitroaniline is a compound useful in organic synthesis. Dyes and metabolites, Environmental Testing.

Chemical Properties

Redish-Brown Solid

General Description

Orange-yellow prisms or brown granular powder.

Air & Water Reactions

2-Methyl-6-nitroaniline is sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

2-Methyl-6-nitroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates, and strong oxidizers.

Fire Hazard

Flash point data for 2-Methyl-6-nitroaniline are not available, but 2-Methyl-6-nitroaniline is probably combustible.

InChI:InChI=1/C7H10N2O2/c1-7(9(10)11)5-3-2-4-6(7)8/h2-6H,8H2,1H3

Synthetic route

2-aminotoluene-5-sulfonic acid (98-33-9) → 2-Methyl-6-nitroaniline (570-24-1)

Conditions	Yield
Stage #1: 2-aminotoluene-5-sulfonic acid With acetic acid; zinc(II) oxide at 80℃; for 4h; Stage #2: With nitric acid at 10 - 12℃; for 2h; Stage #3: With hydrogenchloride In water at 100℃; for 1h;	82%

o-toluidine (95-53-4) → 2-Methyl-6-nitroaniline (570-24-1) + 2-methyl-4-nitro-benzenamine (99-52-5)

Conditions	Yield
With bromine; silver nitrate; triphenylphosphine In acetonitrile at 20℃; for 0.0833333h;	A 15% B 67%
With 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one In acetic acid for 3h; Ambient temperature;	A 30% B 40%
With acetic anhydride anschliessend mit wss.Salpetersaeure und Erwaermen des Reaktionsprodukts mit wss.Salzsaeure;

2-methyl-6-nitroazidobenzene (16714-18-4) + isobutyraldehyde (78-84-2) → 2-Methyl-6-nitroaniline (570-24-1) + 4-methyl-2-(1-methylethyl)benzimidazole + 1,2-dihydro-2,2,5-trimethylquinoxaline

Conditions	Yield
Stage #1: 2-methyl-6-nitroazidobenzene With triphenylphosphine In diethyl ether at 20℃; for 1h; Stage #2: isobutyraldehyde In chloroform for 144h; aza-Wittig reaction; Heating; Stage #3: With carbon monoxide; 1,3-bis-(diphenylphosphino)propane; 1,10-phenanthroline hydrate; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 70℃; under 4560.31 Torr; for 21h; Further stages.;	A 8% B 62% C 11%

N-(2-methylphenyl)acetamide (120-66-1) → 2-Methyl-6-nitroaniline (570-24-1) + 2-methyl-4-nitro-benzenamine (99-52-5)

Conditions	Yield
Stage #1: N-(2-methylphenyl)acetamide With nitric acid at 10 - 12℃; Stage #2: With hydrogenchloride	A 60% B n/a
With nitric acid; acetic acid at 7 - 8℃; man laesst bei Zimmertemperatur stehen, giesst in wenig Wasser, filtriert, und erhitzt das Nitrierungsprodukt mit Salzsaeure; destilliert man hierauf mit Wasserdampf und erhaelt man mit Natronlauge die freie Base;
With nitric acid Nitrierung und Verseifung;
With ammonium nitrate; nitric acid; acetic acid Nitrierung und Verseifung;
With water; nitric acid; acetic acid man versetzt den abfiltrierten Niederschlag mit konz.Salzsaeure und destilliert mit Wasserdampf, wobei 3-Nitro-2-amino-toluol uebergeht, waehrend 5-Nitro-2-amino-toluol in der salzsauren Loesung zurueckbleibt;

N-(2-methyl-6-nitrophenyl)acetamide (59907-22-1) → 2-Methyl-6-nitroaniline (570-24-1) + 2-methyl-4-nitroacetanilide (2719-15-5)

Conditions	Yield
With hydrogenchloride	A 46% B n/a

nitro acetate (591-09-3) + N-(2-methylphenyl)acetamide (120-66-1) → 2-Methyl-6-nitroaniline (570-24-1)

Conditions	Yield
With acetic acid und Erwaermen des Reaktionsprodukts mit wss.Salzsaeure;

N-(2-methylphenyl)acetamide (120-66-1) → 2-Methyl-6-nitroaniline (570-24-1) + 2-methyl-4-nitroacetanilide (2719-15-5)

Conditions	Yield
With nitric acid; acetic anhydride; acetic acid at 15 - 20℃; ueber mehrere Stufen;

1-methyl-2,3-dinitrobenzene (602-01-7) → 2-Methyl-6-nitroaniline (570-24-1)

Conditions	Yield
With ammonia at 150 - 160℃; unter Druck;

N-(2-methyl-6-nitrophenyl)acetamide (59907-22-1) + sodium methylate (124-41-4) → 2-Methyl-6-nitroaniline (570-24-1)

Conditions	Yield
Rate constant;

N-(2-methyl-6-nitrophenyl)acetamide (59907-22-1) → 2-Methyl-6-nitroaniline (570-24-1)

Conditions	Yield
With sodium methylate
With hydrogenchloride
(hydrolysis);

N-(2-methylphenyl)-p-toluenesulphonamide (80-28-4) → 2-Methyl-6-nitroaniline (570-24-1) + 2-methyl-4,6-dinitroaniline (7477-94-3)

Conditions	Yield
bei hoeherer Temperatur erhaelt man ein Gemisch von Nitrierungsprodukten.Hydrolysis;

N,N'-bis(o-tolyl)oxamide (3299-62-5) → 2-Methyl-6-nitroaniline (570-24-1)

Conditions	Yield
With sulfuric acid Schuetteln des Reaktionsprodukts mit Salpeterschwefelsaeure bei hoechstens 50grad und Erhitzen nach Zusatz von Wasser auf 140-150grad;

N-nitro-o-toluidine → 2-Methyl-6-nitroaniline (570-24-1) + 2-methyl-4-nitro-benzenamine (99-52-5)

Conditions	Yield
With mineral acid

6-amino-5-nitro-toluene-3-sulfonic acid → 2-Methyl-6-nitroaniline (570-24-1)

Conditions	Yield
durch Abspaltung der Sulfogruppe;

N-(2-methylphenyl)acetamide (120-66-1) → 2-Methyl-6-nitroaniline (570-24-1)

Conditions	Yield
(i) HNO3, (ii) aq. HCl; Multistep reaction;
With nitric acid
Multi-step reaction with 2 steps 1: nitric acid; acetic anhydride / dichloromethane 2: hydrogenchloride / water / Reflux View Scheme
Stage #1: N-(2-methylphenyl)acetamide With nitric acid In acetic anhydride at 10 - 12℃; for 2.5h; Stage #2: With sulfuric acid In water for 3h; Reflux;	39.78 g

1-methyl-3-nitrobenzene (99-08-1) → 2-Methyl-6-nitroaniline (570-24-1) + 2-methyl-4-nitro-benzenamine (99-52-5) + 4-methyl-2-nitroaniline (89-62-3)

Conditions	Yield
With potassium tert-butylate; N,N,N-trimethylhydrazinium iodide In dimethyl sulfoxide Ambient temperature; Yield given. Yields of byproduct given;

N-(2-methylphenyl)acetamide (120-66-1) → 2-Methyl-6-nitroaniline (570-24-1) + acetyl derivative of 5-nitro-2-amino-toluene

Conditions	Yield
With nitric acid; acetic acid man kocht das entstehende Acetylderiv.in alkoh.Loesung mit der waessr.Kalilauge,wodurch nur das Acetylderiv.des 5-Nitro-2-amino-toluols verseift wird; das Acetylderiv.des 3-Nitro-2-amino-toluols verseift man mit konz.Salzsaeure;

1-methyl-2,3-dinitrobenzene (602-01-7) + ammonia (7664-41-7) → 2-Methyl-6-nitroaniline (570-24-1)

Conditions	Yield
at 150 - 160℃; unter Druck;

sulfuric acid (7664-93-9) + N,N'-bis(o-tolyl)oxamide (3299-62-5) → 2-Methyl-6-nitroaniline (570-24-1)

Conditions	Yield
anschliessenden Schuetteln mit Salpeterschwefelsaeure unterhalb 50grad und Erhitzen mit Wasser auf 140-150grad;

sulfuric acid (7664-93-9) + 6-amino-5-nitro-toluene-3-sulfonic acid → 2-Methyl-6-nitroaniline (570-24-1)

hydrogenchloride (7647-01-0) + diethyl ether (60-29-7) + N-nitro-o-toluidine → 2-Methyl-6-nitroaniline (570-24-1) + 2-methyl-4-nitro-benzenamine (99-52-5)

Conditions	Yield
at 0℃;

o-toluidine (95-53-4) + chloric acid → 2-Methyl-6-nitroaniline (570-24-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 12 - 13 °C 2.1: 65 percent HNO3 / 10 - 12 °C 2.2: 60 percent / conc. HCl View Scheme
Multi-step reaction with 2 steps 2: HNO3 View Scheme

o-toluidine (95-53-4) + ester of glycine → 2-Methyl-6-nitroaniline (570-24-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / HNO3 2: concd. HCl / 7 h / Heating View Scheme

o-toluidine (95-53-4) → 2-Methyl-6-nitroaniline (570-24-1)

Conditions	Yield
Multi-step reaction with 2 steps 2: acetic acid anhydride; glacial acetic acid; nitric acid / 15 - 20 °C / ueber mehrere Stufen View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane 2: nitric acid; acetic anhydride / dichloromethane 3: hydrogenchloride / water / Reflux View Scheme

N-(2-methylphenyl)acetamide (120-66-1) + calcium chloride → 2-Methyl-6-nitroaniline (570-24-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: (nitration) 2: aq. HCl View Scheme

2-Methyl-6-nitroaniline (570-24-1) → 4-iodo-2-methyl-6-nitroaniline (532934-93-3)

Conditions	Yield
With Iodine monochloride; acetic acid at 30℃; for 3h;	100%
With sodium acetate; Iodine monochloride; acetic acid at 80℃; for 0.833333h;	98%
With N-iodo-succinimide; acetic acid at 50 - 55℃; for 6h; Inert atmosphere;	97%
With Iodine monochloride; acetic acid
With Iodine monochloride; sodium hydrogencarbonate In methanol; dichloromethane at 20℃; for 6h;

2-Methyl-6-nitroaniline (570-24-1) + benzaldehyde (100-52-7) → 4-methyl-2-phenyl-1H-benzimidazole (3659-77-6)

Conditions	Yield
With hydrogen In ethyl acetate at 60℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry;	99%
With hydrogen In ethyl acetate at 60℃; under 7500.75 Torr; for 20h; Autoclave;	99%

2-Methyl-6-nitroaniline (570-24-1) → 4-chloro-2-methyl-6-nitrophenylamine (62790-50-5)

Conditions	Yield
With N-chloro-succinimide In methanol at 60℃; for 4h;	98%
With N-chloro-succinimide; acetic acid	92%
With N-chloro-succinimide; acetic acid at 50 - 55℃; for 6h; Inert atmosphere;	92%

2-Methyl-6-nitroaniline (570-24-1) → 7-Nitroindazole (2942-42-9)

Conditions	Yield
With acetic acid; sodium nitrite for 0.333333h;	98%
With acetic acid; sodium nitrite In water	98%
With acetic acid; sodium nitrite In water at 20℃; for 0.333333h; Inert atmosphere;	97%

2-Methyl-6-nitroaniline (570-24-1) + benzyl bromide (100-39-0) → 1-Benzyloxy-4-methyl-2-phenyl-1H-benzoimidazole (161958-74-3)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 16h; Heating;	98%

2-Methyl-6-nitroaniline (570-24-1) + acetylacetone (123-54-6) → 3-(2-mehtyl-6-nitrophenylhydrazono)pentane-2,4-dione (864652-84-6)

Conditions	Yield
Stage #1: 2-Methyl-6-nitroaniline With hydrogenchloride; sodium nitrite Stage #2: acetylacetone With sodium hydroxide; sodium acetate In methanol; water at 0 - 20℃; for 1h; Further stages.;	98%

2-Methyl-6-nitroaniline (570-24-1) → 4-bromo-2-methyl-6-nitroaniline (77811-44-0)

Conditions	Yield
With hydrogen bromide; dihydrogen peroxide In ethanol; water at 60℃; for 1h; Product distribution / selectivity;	97.7%
With N-Bromosuccinimide; acetic acid at 50 - 55℃; for 6h; Inert atmosphere;	93%
With sodium tungstate; dihydrogen peroxide; acetic acid; potassium bromide for 1h; Ambient temperature;	90%
With sodium tungstate; sodium perborate; sulfuric acid; acetic anhydride; potassium bromide In acetic acid for 1h; Ambient temperature;	69%
With N-Bromosuccinimide In tetrachloromethane Substitution; bromination;	60%

2-Methyl-6-nitroaniline (570-24-1) → 3-methyl-1,2-benzenediamine (2687-25-4)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In ethanol at 20℃; under 760.051 Torr; for 4h;	97%
With hydrogenchloride; tin for 1h; Reflux;	85.8%
Stage #1: 2-Methyl-6-nitroaniline With tin(ll) chloride In ethyl acetate for 6h; Reflux; Stage #2: With water; sodium hydrogencarbonate In ethyl acetate Cooling;	70%

2-Methyl-6-nitroaniline (570-24-1) + 2-Bromoacetyl bromide (598-21-0) → C9H9BrN2O3

Conditions	Yield
With potassium carbonate In dichloromethane; water at 0℃; for 1h;	97%
With sodium carbonate In water for 0.5h; pH=8 - 9;
With sodium carbonate In water for 2h;

2-Methyl-6-nitroaniline (570-24-1) + acrylic acid (79-10-7) → 3-(2-methyl-6-nitrophenylamino)propionic acid (1296194-25-6)

Conditions	Yield
With sulfuric acid at 25 - 80℃; Inert atmosphere;	96%

2-Methyl-6-nitroaniline (570-24-1) + orthobenzoic acid trimethyl ester (707-07-3) → 4-methyl-2-phenyl-1H-benzimidazole (3659-77-6)

Conditions	Yield
With indium; acetic acid In ethyl acetate for 1h; Reflux; Inert atmosphere;	96%

2-chloro-3-methoxypyridine (52605-96-6) + 2-Methyl-6-nitroaniline (570-24-1) → C13H13N3O3

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); C35H38NO4P In 1,4-dioxane at 100℃; for 18h;	96%

2-Methyl-6-nitroaniline (570-24-1) → 2-iodo-3-nitrotoluene (6277-17-4)

Conditions	Yield
Stage #1: 2-Methyl-6-nitroaniline With sodium nitrite In sulfuric acid; acetic acid Stage #2: With potassium iodide In sulfuric acid; water; acetic acid Further stages.;	95%
Stage #1: 2-Methyl-6-nitroaniline With hydrogenchloride In water at 0℃; for 0.25h; Stage #2: With sodium nitrite In water at 0℃; for 1.67h; Stage #3: With potassium iodide In water at 0℃; for 2.17h;	88%
Stage #1: 2-Methyl-6-nitroaniline With sulfuric acid; sodium nitrite In acetic acid at 15 - 75℃; Stage #2: With urea; potassium iodide	79%

2-Methyl-6-nitroaniline (570-24-1) + 2-chloro-5-[(3,5-dimethoxyphenyl)methoxy]pyrimidine (1453211-57-8) → 5-[(3,5-dimethoxyphenyl)methoxy]-N-(2-methyl-6-nitrophenyl)pyrimidin-2-amine

Conditions	Yield
With caesium carbonate; bis(dibenzylideneacetone)-palladium(0); XPhos In N,N-dimethyl acetamide at 110℃; for 3h; Inert atmosphere;	94%

2-Methyl-6-nitroaniline (570-24-1) → 2-bromo-3-nitrotoluene (41085-43-2)

Conditions	Yield
With hydrogen bromide; copper(I) bromide; sodium nitrite In 1,4-dioxane; water at 0 - 60℃;	93%
Stage #1: 2-Methyl-6-nitroaniline With hydrogen bromide In 1,4-dioxane; water at 60℃; for 0.75h; Inert atmosphere; Stage #2: With sodium nitrite In 1,4-dioxane; water at 0 - 8℃; for 2.33333h; Inert atmosphere; Stage #3: With hydrogen bromide; copper(I) bromide In 1,4-dioxane; water at 20 - 60℃; for 20.5h; Inert atmosphere;	82%
Stage #1: 2-Methyl-6-nitroaniline With hydrogen bromide In 1,4-dioxane; water at 60℃; for 0.75h; Inert atmosphere; Stage #2: With sodium nitrite In 1,4-dioxane; water at 0 - 5℃; Inert atmosphere; Stage #3: With hydrogen bromide; copper(I) bromide In 1,4-dioxane; water at 24 - 60℃; Inert atmosphere;	81%

2-Methyl-6-nitroaniline (570-24-1) + allyl bromide (106-95-6) → 1-allyloxy-4-methyl-2-vinylbenzimidazole (161958-75-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 16h; Heating;	92%

2-Methyl-6-nitroaniline (570-24-1) + naphthalene-1-carbonic acid chloride (879-18-5) → Naphthalene-1-carboxylic acid (2-methyl-6-nitro-phenyl)-amide (212503-73-6)

Conditions	Yield
With pyridine In tetrahydrofuran for 6h; Ambient temperature;	91%

2-Methyl-6-nitroaniline (570-24-1) + acetic anhydride (108-24-7) → N-(2-methyl-6-nitrophenyl)acetamide (59907-22-1)

Conditions	Yield
In chloroform for 12h; Time; Reflux;	90.2%
With sulfuric acid

2-Methyl-6-nitroaniline (570-24-1) + cyclohexane-1,2-epoxide (286-20-4) → (1R,2R)-2-(2-Methyl-6-nitro-phenylamino)-cyclohexanol + trans-2-chlorocyclohexanol (6628-80-4)

Conditions	Yield
With bismuth(III) chloride In cyclohexane at 20℃;	A 90% B n/a

2-Methyl-6-nitroaniline (570-24-1) → 1,3-bis(2-methyl-6-nitrophenyl)-2λ4-diazathia-1,2-diene (1431381-87-1)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; disulfur dichloride In chloroform at -30℃; for 2h; Reflux;	90%

2-Methyl-6-nitroaniline (570-24-1) + 4-chlorobenzenesulfonyl chloride (98-60-2) → N-(2-methyl-6-nitrophenyl)-4-chlorobenzenesulfonamide

Conditions	Yield
With sodium carbonate In water pH=9 - 10;	89%

2-Methyl-6-nitroaniline (570-24-1) + dimethylglyoxal (431-03-8) → 5-methyl-2,3-dimethylquinoxaline (17635-19-7)

Conditions	Yield
With indium; indium(III) chloride In methanol for 2.5h; Reflux; Inert atmosphere;	89%

2-Methyl-6-nitroaniline (570-24-1) + benzil (134-81-6) → 5-methyl-2,3-diphenylquinoxaline

Conditions	Yield
With indium; indium(III) chloride In methanol for 1.66667h; Reagent/catalyst; Reflux; Inert atmosphere;	89%

2-Methyl-6-nitroaniline (570-24-1) + 2.3-butanediol (513-85-9) → 5-methyl-2,3-dimethylquinoxaline (17635-19-7)

Conditions	Yield
With sodium hydroxide In toluene at 120℃; for 3h; Inert atmosphere; Sealed tube; Green chemistry;	89%
With dodecacarbonyl-triangulo-triruthenium; cesiumhydroxide monohydrate; 1,3-bis-(diphenylphosphino)propane In tert-Amyl alcohol at 150℃; for 8h; Schlenk technique; Inert atmosphere;	80%

2-Methyl-6-nitroaniline (570-24-1) + 1-Bromo-2-bromomethyl-benzene (3433-80-5) → 1-(o-bromobenzyloxy)-2-(o-bromophenyl)-4-methylbenzimidazole

Conditions	Yield
With sodium hydride In tetrahydrofuran for 12h; Heating;	87%

2-Methyl-6-nitroaniline (570-24-1) → 3-bromo-2-methyl-6-nitroaniline

Conditions	Yield
With N-Bromosuccinimide; acetic acid for 2h; Reflux; Inert atmosphere;	87%
With N-Bromosuccinimide; acetic acid for 2h; Reflux;	87%

2-Methyl-6-nitroaniline (570-24-1) → 1-methyl-2,3-dinitrobenzene (602-01-7)

Conditions	Yield
With sodium perborate; titanium(IV) hydroxide; acetic acid at 90 - 100℃; for 1h; Inert atmosphere;	86.8%
With dihydrogen peroxide In acetic acid at 90℃; for 3h;	48%
With sulfuric acid Diazotization.Ueberfuehrung des Diazoniumsulfats in das Nitrit und Behandeln mit Kupfer(I)-oxyd;

2-Methyl-6-nitroaniline (570-24-1) + sodium hydrogensulfite → 2-iodo-3-nitrotoluene (6277-17-4)

Conditions	Yield
With potassium iodide; sulfuric acid; sodium nitrite In ice-water; ethanol; dichloromethane	84%

2-Methyl-6-nitroaniline (570-24-1) + 9,10-phenanthrenequinone (84-11-7) → 10-methyldibenzo[a,c]phenazine (112657-94-0)

Conditions	Yield
With indium; acetic acid In methanol for 0.166667h; Reflux; Inert atmosphere;	84%

2-Methyl-6-nitroaniline (570-24-1) + acetic anhydride (108-24-7) → N,N-diacetyl-6-nitro-o-toluidine (82344-53-4)

Conditions	Yield
at 120℃; for 12.5h;	83.7%

Upstream product

• 80-28-4 N-(2-methylphenyl)-p-toluenesulphonamide 
• 95-53-4 o-toluidine 
• 120-66-1 N-(2-methylphenyl)acetamide 
• 99-08-1 1-methyl-3-nitrobenzene 
• 7664-93-9 sulfuric acid 
• 3299-62-5 N,N'-bis(o-tolyl)oxamide 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 602-01-7 1-methyl-2,3-dinitrobenzene 
• 59907-22-1 N-(2-methyl-6-nitrophenyl)acetamide 
• 7664-41-7 ammonia 
• 124-41-4 sodium methylate 
• 591-09-3 nitro acetate 
• 98-33-9 2-aminotoluene-5-sulfonic acid 

Downstream Products

• 191847-67-3 N-(2-methyl-6-nitrophenyl)glycine 
• 343616-55-7 4-methyl-N-(2-methyl-6-nitrophenyl)benzenesulfonamide 
• 36894-31-2 morpholine-4-carboxylic acid 2-methyl-6-nitro-anilide 
• 57729-89-2 (2,4-Dinitro-6-trifluoromethyl-phenyl)-(2-methyl-6-nitro-phenyl)-amine 
• 84186-28-7 2-piperidino-3-nitrotoluene 
• 93415-73-7 N-(2'-Methyl-6'-nitrophenyl)-5-amino-6-nitro-1,3-benzdioxol 
• 87399-27-7 Bicyclo<4.4.1>undeca-3,6,8,10-tetraen-2,5-dion-2-(2-methyl-6-nitrophenylhydrazon) 
• 123259-46-1 (2-Methyl-6-nitro-phenyl)-carbamic acid (1R,3R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester; hydrochloride 
• 93415-75-9 N-(2'-Methyl-6'-nitrophenyl)-5-amino-4,7-dimethyl-6-nitro-1,3-benzdioxol 
• 3523-86-2 4-methylbenzofurazan oxide 
• 109670-19-1 2,2'-dimethyl-6,6'-dinitroazobenzene 
• 62790-50-5 4-chloro-2-methyl-6-nitrophenylamine 
• 59483-66-8 N-chloro-6-methyl-2-nitroaniline 
• 2942-42-9 7-Nitroindazole 

Relevant articles and documents

Microwave-assisted reduction of aromatic nitro compounds with novel oxo-rhenium complexes

The reduction of several aromatic nitro compounds to amines by means of the two novel catalytic systems ([IMes]2ReOBr3)/PhSiH3 and ([Py]3ReNOBr2)/PhSiH3 under microwave irradiation is here reported. These two systems were able to perform the reduction of nitro groups with higher TON and TOF when compared with previously reported systems based on oxo-rhenium core under standard heating, although they showed a lesser broad reaction scope compared with the known systems.

Selectivity of the complexation reactions of four regioisomeric methylcamphorquinoxaline ligands with gold(III): X-ray, NMR and DFT investigations

Reported are the synthesis, spectral and structural characteristics of new quinoxaline-related regioisomeric ligands L1-L4 (1,x,11,11-tetramethyl-1,2,3,4-tetrahydro-1,4-methanophenazine, x = 7, 8, 9 and 6, respectively) and their mononuclear Au(III) complexes (1-4). Fusion of the camphor moiety to the quinoxaline core made two N-atoms of quinoxaline nonequivalent while the introduction of a methyl-substituent at positions 6-9 enabled a tuning of coordination properties of L1-L4. Gold(III) complexes 1-4 and ligands L1-L4 have been studied in detailed by 1D and 2D NMR and the structures of 1-4 have been determined by X-ray crystallography. The results of these analyses revealed a regiospecific coordination of Au(III) to the sterically less hindered N-5 atom (spatially close to the non-substituted bridgehead carbon) of L1-L3, and to N-10 (spatially close to the methyl-substituted bridgehead carbon) of L4. The results of DFT calculations shed light on disparate coordination modes of L1-L4 toward the AuCl3 fragment and explain formation of single coordination products in high yield.

SUBSTITUTED AROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The invention relates to substituted aromatic carboxamide and urea derivatives, to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions (formula (I)).