601-87-6

Basic information

• Product Name: 3-Methyl-2-nitroaniline
• Synonyms: 2-NITRO-M-TOLUIDINE;3-AMINO-2-NITROTOLUENE;3-Methyl-2-nitrobenzenamine;3-METHYL-2-NITROANILINE;2-NITRO-3-METHYL ANILINE;3-Amino-2-nitrotoluene, 2-Amino-6-methyl-1-nitrobenzene;3-Methyl-2-nitroaniline 97%;3-Amino-2-nitrotoluene, 2-Amino-6-methylnitrobenzene
• CAS NO: 601-87-6
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.15
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives
• Mol File: 601-87-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 107-108 °C
• Boiling Point: 288.553 °C at 760 mmHg
• Flash Point: 128.313 °C
• Appearance: /
• Density: 1.27 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.616
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -0.11±0.10(Predicted)
• CAS DataBase Reference: 3-Methyl-2-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-2-nitroaniline(601-87-6)
• EPA Substance Registry System: 3-Methyl-2-nitroaniline(601-87-6)

Safety Data

• Hazardous Substances Data: 601-87-6(Hazardous Substances Data)

Usage

Uses

3-Methyl-2-nitroaniline is used in the purification of 2-Methoxy-5-trifluoromethoxybenzaldehyde. It also an important component in preparing benzimidazoles. It is used in palladium-catalyzed synthesis of quinoxline deriitives.

InChI:InChI=1/C7H8N2O2/c1-5-3-2-4-6(8)7(5)9(10)11/h2-4H,8H2,1H3

Synthetic route

3-Methyl-2-nitrobenzenecarboxamide (60310-07-8) → 3-methyl-2-nitroaniline (601-87-6)

Conditions	Yield
With bromine; sodium hydroxide In water at 0 - 80℃; for 2h;	90%
With bromine; sodium hydroxide In water at 0 - 80℃; for 2h;	90%
With bromine; sodium hydroxide In water at 0 - 80℃; for 2h;	90%

4-methyl-benzofuroxan (27808-46-4) → 3-methyl-2-nitroaniline (601-87-6)

Conditions	Yield
With iron(II) sulfate In water; dimethyl sulfoxide for 48h; Ambient temperature;	90%
With HbO2(2+) In phosphate buffer; dimethyl sulfoxide for 1h; pH=7.4;	100 % Chromat.

1-methyl-2,3-dinitrobenzene (602-01-7) → 3-methyl-2-nitroaniline (601-87-6)

Conditions	Yield
With hydrogenchloride; ethanol; tin(ll) chloride at 7℃;
With tin(ll) chloride

3-chloro-2-nitrotoluene (5367-26-0) → 3-methyl-2-nitroaniline (601-87-6)

Conditions	Yield
With ammonia at 200℃; im Rohr;

3-methyl-2-nitrobenzoic acid (5437-38-7) → 3-methyl-2-nitroaniline (601-87-6)

Conditions	Yield
With sodium azide; sulfuric acid
Multi-step reaction with 3 steps 3: Br2, KOH View Scheme
Multi-step reaction with 3 steps 1: PCl5 2: HCO2NH4 3: Br2, aq. KOH View Scheme

sulfuric acid (7664-93-9) + 1-amino-3-methylbenzene (108-44-1) + HNO3+H2SO4 → 4-nitro-3-methylaniline (611-05-2) + 3-methyl-2-nitroaniline (601-87-6) + 5-methyl-2-nitroaniline (578-46-1)

Conditions	Yield
Nitrieren;

1-methyl-2,3-dinitrobenzene (602-01-7) + ammonium sulfide → 3-methyl-2-nitroaniline (601-87-6)

hydrogenchloride (7647-01-0) + 1-methyl-2,3-dinitrobenzene (602-01-7) + tin (II)-chloride → 3-methyl-2-nitroaniline (601-87-6)

3-chloro-2-nitrotoluene (5367-26-0) + ammonia (7664-41-7) → 3-methyl-2-nitroaniline (601-87-6)

Conditions	Yield
at 200℃;

3-methyl-2-nitrobenzoyl chloride (50424-93-6) → 3-methyl-2-nitroaniline (601-87-6)

Conditions	Yield
Multi-step reaction with 2 steps 2: Br2, KOH View Scheme
Multi-step reaction with 2 steps 1: benzene 2: aqueous potassium hypobromite View Scheme
Multi-step reaction with 2 steps 1: HCO2NH4 2: Br2, aq. KOH View Scheme

4-acetylamino-2-nitrotoluene (2719-14-4) → 3-methyl-2-nitroaniline (601-87-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) HNO3, (ii) H2SO4, EtOH 2: (deamination) 3: SnCl2 View Scheme

2,3-dinitro-4-methylaniline (70343-09-8) → 3-methyl-2-nitroaniline (601-87-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: (deamination) 2: SnCl2 View Scheme

m-Toluic acid (99-04-7) → 3-methyl-2-nitroaniline (601-87-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: HNO3 2: PCl5 3: HCO2NH4 4: Br2, aq. KOH View Scheme

1-fluoro-3-methyl-2-nitro-benzene (3013-27-2) → 3-methyl-2-nitroaniline (601-87-6)

Conditions	Yield
With ammonium hydroxide In ethanol; water at 0 - 80℃; for 24h; Sealed tube;

3-methyl-2-nitroaniline (601-87-6) → 3-amino-8-methyl-1,2,4-benzotriazine 1-oxide (157284-01-0)

Conditions	Yield
	100%
Multi-step reaction with 2 steps 1: HCl / 100 °C 2: 100 percent / aq. NaOH / 1 h / 100 °C View Scheme

3-methyl-2-nitroaniline (601-87-6) → 3-methyl-1,2-benzenediamine (2687-25-4)

Conditions	Yield
With palladium 10% on activated carbon; ammonium formate In methanol at 70℃; for 3h;	98%
With tin(II) chloride dihdyrate In ethyl acetate at 20℃;	62%
durch Reduktion;
With hydrogen In methanol at 20℃; under 1551.49 Torr; for 2h;
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 2h; High pressure;

3-methyl-2-nitroaniline (601-87-6) + 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;	97%
With hydrogen In ethyl acetate at 60℃; under 7500.75 Torr; for 20h; Autoclave;	97%

3-methyl-2-nitroaniline (601-87-6) → 4-methylbenzofurazan oxide (3523-86-2)

Conditions	Yield
With sodium hydroxide; sodium hypochlorite In ethanol at 25℃; for 0.0833333h;	96%

3-methyl-2-nitroaniline (601-87-6) + naphthalene-1-carbonic acid chloride (879-18-5) → N-(1-naphthoyl)-2-methyl-2-nitroanilide (199594-51-9)

Conditions	Yield
for 7h;	91%

3-methyl-2-nitroaniline (601-87-6) + 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;	90%

3-methyl-2-nitroaniline (601-87-6) → 1-iodo-3-methyl-2-nitrobenzene (52414-99-0)

Conditions	Yield
Stage #1: 3-methyl-2-nitroaniline With sulfuric acid; sodium nitrite In water cooling; Stage #2: With copper; potassium iodide In water at 80℃; for 0.5h;	88%
Diazotieren und Behandeln mit Kaliumjodid Loesung;

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 3-methyl-2-nitroaniline (601-87-6) → C11H10N2O2 (1224955-41-2)

Conditions	Yield
With acetic acid at 120℃; for 1h; Inert atmosphere;	87%
With acetic acid for 1h; Reflux;	87%

3-methyl-2-nitroaniline (601-87-6) + acetic anhydride (108-24-7) → N-(3-methyl-2-nitrophenyl)acetamide (90868-29-4)

Conditions	Yield
With sulfuric acid In acetic acid at 90℃; for 0.666667h;	85%
With sulfuric acid

3-methyl-2-nitroaniline (601-87-6) → 6-bromo-3-methyl-2-nitroaniline

Conditions	Yield
With N-Bromosuccinimide; acetic acid at 120℃; for 4h;	80%

3-methyl-2-nitroaniline (601-87-6) → 4-bromo-3-methyl-2-nitro-aniline (854624-54-7)

Conditions	Yield
With N-Bromosuccinimide; acetic acid at 110℃; for 1h;	78%
With N-Bromosuccinimide; acetic acid at 110℃; for 1h;	78%
With N-Bromosuccinimide; acetic acid at 110℃; for 1h;	78%

3-methyl-2-nitroaniline (601-87-6) + 2-naphthaloyl chloride (2243-83-6) → N-(2-naphthoyl)-2-methyl-2-nitroanilide (199594-52-0)

Conditions	Yield
for 7h;	75%

carbon monoxide (201230-82-2) + 3-methyl-2-nitroaniline (601-87-6) → 4-methyl-1,3-dihydro-2H-benzoimidazol-2-one (19190-68-2)

Conditions	Yield
With selenium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In toluene at 150℃; under 22800 Torr; for 4h;	71%

3-methyl-2-nitroaniline (601-87-6) + acetaldehyde (75-07-0) → 3-(N-Ethylamino)-2-nitrotoluene (160984-53-2)

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol for 15h; Ambient temperature;	65%

3-methyl-2-nitroaniline (601-87-6) + benzene 1,3,5-triyl triformate → 4-methyl-1,3-dihydro-2H-benzoimidazol-2-one (19190-68-2)

Conditions	Yield
With selenium; triethylamine In N,N-dimethyl-formamide at 120℃; Inert atmosphere; Sealed tube;	62%

3-methyl-2-nitroaniline (601-87-6) + benzene (71-43-2) → 3-methyl-2-nitro-[1,1 '-biphenyl] (82617-45-6)

Conditions	Yield
With hydrogenchloride; potassium acetate; sodium nitrite 1.) 0 deg C, 2.) 5-10 deg C, 4 h, 3.) RT, 24 h;	61%

1,2-Cyclohexanediol (931-17-9) + 3-methyl-2-nitroaniline (601-87-6) → 6-methyl-1,2,3,4-tetrahydrophenazine

Conditions	Yield
With potassium phosphate monohydrate; trimethylamine-N-oxide; C18H27FeO4Si2 In toluene at 150℃; for 48h; Inert atmosphere; Schlenk technique; Sealed tube;	61%

3-methyl-2-nitroaniline (601-87-6) → 1-bromo-3-methyl-2-nitro-benzene (52414-97-8)

Conditions	Yield
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 65℃; for 0.25h; Heating / reflux;	57%
With hydrogen bromide Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuBr;

tert.-butylnitrite (540-80-7) + 3-methyl-2-nitroaniline (601-87-6) → 1-bromo-3-methyl-2-nitro-benzene (52414-97-8)

Conditions	Yield
With copper(I) bromide In acetonitrile at 65℃; for 0.25h; Heating / reflux;	57%

3-methyl-2-nitroaniline (601-87-6) + pyridine-3-carbonyl chloride hydrochloride (20260-53-1) → N-nicotinoyl-2-methyl-6-nitroanilide (212503-75-8)

Conditions	Yield
	55%

3-methyl-2-nitroaniline (601-87-6) + 2,6-difluorobenzoylchloride (18063-02-0) → N-(2,6-difluorobenzoyl)-2-methyl-6-nitroaniline (212503-70-3)

Conditions	Yield
	55%

3-methyl-2-nitroaniline (601-87-6) + isonicotinoyl chloride hydrochloride (39178-35-3) → N-isonicotinoyl-2-methyl-6-nitroanilide (212503-71-4)

Conditions	Yield
for 4h;	53%

3-methyl-2-nitroaniline (601-87-6) + 5-(1-(3,5-dichloropyridin-4-yl)ethoxy)-1H-indazole-3-carbaldehyde → 5-(1-(3,5-dichloropyridin-4-yl)ethoxy)-3-(4-methyl-1H-benzo[d]-imidazol-2-yl)-1H-indazole

Conditions	Yield
Stage #1: 3-methyl-2-nitroaniline With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 2h; Stage #2: 5-(1-(3,5-dichloropyridin-4-yl)ethoxy)-1H-indazole-3-carbaldehyde With sulfur In N,N-dimethyl-formamide at 90℃; for 2h; Inert atmosphere;	51%

bromobenzene (108-86-1) + 3-methyl-2-nitroaniline (601-87-6) → 3-methyl-2-nitrodiphenylamine (220495-97-6)

Conditions	Yield
With copper(l) iodide; potassium carbonate for 16h; Heating;	45%

3-methyl-2-nitroaniline (601-87-6) + isobutyraldehyde (78-84-2) → 3-methyl-2-nitro-N-(2-methyl-1-propen-1-yl)benzenamine

Conditions	Yield
With 4 A molecular sieve In benzene at 20℃; for 72h;	36%

formaldehyd (50-00-0) + 3-methyl-2-nitroaniline (601-87-6) → 3-methyl-2-nitro-N-methylaniline (70254-75-0)

Conditions	Yield
With sulfuric acid for 1h;	29%

4-bromophenethanol (4654-39-1) + 3-methyl-2-nitroaniline (601-87-6) → 2-[4-(3-methyl-2-nitroanilino)phenyl]ethanol

Conditions	Yield
With copper(l) iodide; potassium carbonate at 200℃; for 2h; in a sealed tube;	21%
With CuI; potassium carbonate	700 mg (21%)

phthalic anhydride (85-44-9) + 3-methyl-2-nitroaniline (601-87-6) → 2-(3-Methyl-2-nitro-phenyl)-isoindole-1,3-dione

Conditions	Yield
In pentan-1-ol for 12h; Heating;	15%

Upstream product

• 27808-46-4 4-methyl-benzofuroxan 
• 7664-93-9 sulfuric acid 
• 108-44-1 1-amino-3-methylbenzene 
• 602-01-7 1-methyl-2,3-dinitrobenzene 
• 3013-27-2 1-fluoro-3-methyl-2-nitro-benzene 
• 99-04-7 m-Toluic acid 
• 70343-09-8 2,3-dinitro-4-methylaniline 
• 2719-14-4 4-acetylamino-2-nitrotoluene 
• 50424-93-6 3-methyl-2-nitrobenzoyl chloride 
• 5367-26-0 3-chloro-2-nitrotoluene 
• 7664-41-7 ammonia 
• 7647-01-0 hydrogenchloride 
• 5437-38-7 3-methyl-2-nitrobenzoic acid 
• 60310-07-8 3-Methyl-2-nitrobenzenecarboxamide 

Downstream Products

• 7471-63-8 8-nitro-7-methylquinoline 
• 140112-52-3 (Z)-Octadec-9-enoic acid (3-methyl-2-nitro-phenyl)-amide 
• 278179-09-2 4-methoxy-N-(3-methyl-2-nitro-phenyl)-benzenesulfonamide 
• 14294-33-8 3-methyl-[1,1'-biphenyl]-2-amine 
• 112421-99-5 4-methyl-6-phenylphenanthridine 
• 112421-98-4 N-(2-methyl-6-phenylphenyl)benzamide 
• 112422-17-0 6-(2-Chloro-phenyl)-4-methyl-phenanthridine 
• 112422-21-6 6-(4-Fluoro-phenyl)-4-methyl-phenanthridine 
• 112422-19-2 6-(3-Chloro-phenyl)-4-methyl-phenanthridine 
• 112422-22-7 6-(4-Chloro-phenyl)-4-methyl-phenanthridine 
• 112422-23-8 6-(4-Bromo-phenyl)-4-methyl-phenanthridine 
• 112422-24-9 6-(4-Iodo-phenyl)-4-methyl-phenanthridine 
• 112422-26-1 6-(4-Methoxy-phenyl)-4-methyl-phenanthridine 
• 112422-00-1 6-phenylphenanthridine-4-carboxylic acid 

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