Product Name

  • Name

    2-Methyl-3-nitroaniline

  • EINECS 210-059-6
  • CAS No. 603-83-8
  • Article Data29
  • CAS DataBase
  • Density 1.269 g/cm3
  • Solubility <0.1 g/100 mL at 23 °C in water
  • Melting Point 88-90 °C(lit.)
  • Formula C7H8N2O2
  • Boiling Point 304.7 °C at 760 mmHg
  • Molecular Weight 152.153
  • Flash Point 138.1 °C
  • Transport Information UN 2660 6.1/PG 3
  • Appearance Yellow to greenish-yellow crystalline powder
  • Safety 28-36/37-45-61-28A
  • Risk Codes 23/24/25-33-51/53
  • Molecular Structure Molecular Structure of 603-83-8 (2-Methyl-3-nitroaniline)
  • Hazard Symbols ToxicT, DangerousN
  • Synonyms o-Toluidine,3-nitro- (8CI);1-Amino-2-methyl-3-nitrobenzene;2-Amino-6-nitrotoluene;2-Methyl-3-nitrobenzenamine;3-Nitro-o-toluidine;6-Amino-2-nitrotoluene;6-Nitro-2-aminotoluene;NSC 227939;NSC 25011;
  • PSA 71.84000
  • LogP 2.58980

Synthetic route

2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

Conditions
ConditionsYield
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%
o-toluidine
95-53-4

o-toluidine

A

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

B

4-nitro-2-amino-toluene and 5-nitro-2-amino-toluene

4-nitro-2-amino-toluene and 5-nitro-2-amino-toluene

Conditions
ConditionsYield
With sulfuric acid; nitric acid
N-(2-methylphenyl)phthalimide
2464-33-7

N-(2-methylphenyl)phthalimide

ammonia
7664-41-7

ammonia

A

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

B

2-methyl-5-nitroaniline
99-55-8

2-methyl-5-nitroaniline

Conditions
ConditionsYield
at 100℃; Zuerst nitrieren die Ausgangverbindung;
...Expand
phthalyl-o-toluidine

phthalyl-o-toluidine

A

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

B

2-methyl-5-nitroaniline
99-55-8

2-methyl-5-nitroaniline

Conditions
ConditionsYield
Nitrieren und Verseifung der entstandenen Phthalylnitrotoluidine mit alkoh.Ammoniak im Autoklaven bei 100grad;
durch Nitrieren und Verseifen der gebildeten Phthalylnitrotoluidine mit alkoh.Ammoniak bei 100grad;
sulfuric acid
7664-93-9

sulfuric acid

o-toluidine
95-53-4

o-toluidine

A

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

B

2-methyl-4-nitro-benzenamine
99-52-5

2-methyl-4-nitro-benzenamine

C

2-methyl-5-nitroaniline
99-55-8

2-methyl-5-nitroaniline

Conditions
ConditionsYield
beim Nitrieren;
...Expand
ethanol
64-17-5

ethanol

2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

ammonium sulfide

ammonium sulfide

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

...Expand
hydrogenchloride
7647-01-0

hydrogenchloride

2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

CuCl2

CuCl2

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

Conditions
ConditionsYield
bei der elektrolytischen Reduktion;
...Expand
ethanol
64-17-5

ethanol

2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

platinum black

platinum black

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

Conditions
ConditionsYield
Hydrogenation;
...Expand
ethanol
64-17-5

ethanol

2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

ethyl acetate
141-78-6

ethyl acetate

sodium hydrosulfide

sodium hydrosulfide

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

...Expand
ethanol
64-17-5

ethanol

2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

palladium charcoal

palladium charcoal

A

2-hydroxylamino-6-nitrotoluene
5805-95-8

2-hydroxylamino-6-nitrotoluene

B

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

Conditions
ConditionsYield
Hydrogenation;
...Expand
2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

hydrogen sulfide
7783-06-4

hydrogen sulfide

ammonia
7664-41-7

ammonia

A

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

B

2-nitro-3-oxy-6-amino-toluene

2-nitro-3-oxy-6-amino-toluene

Conditions
ConditionsYield
Behandlung des Reaktionsproduktes mit Salzsaeure;
...Expand
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

(2-methyl-3-nitro-phenyl)-carbamic acid ethyl ester
381670-28-6

(2-methyl-3-nitro-phenyl)-carbamic acid ethyl ester

Conditions
ConditionsYield
In 1,4-dioxane at 65℃; for 24h;100%
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

nitro-4 indazole
2942-40-7

nitro-4 indazole

Conditions
ConditionsYield
With sodium nitrite In water; acetic acid99%
With acetic acid; sodium nitrite at 20℃;95%
With sodium nitrite In water; acetic acid at 45 - 55℃; for 1h; Large scale;95%
formic acid
64-18-6

formic acid

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

N-(2-methyl-3-nitrophenyl)formamide
133053-87-9

N-(2-methyl-3-nitrophenyl)formamide

Conditions
ConditionsYield
at 100℃; for 3h;99%
4-chloro-3-formylcoumarin
50329-91-4

4-chloro-3-formylcoumarin

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

4-(2-hydroxyphenyl)-8-methyl-7-nitroquinoline-3-carboxylic acid
1394232-20-2

4-(2-hydroxyphenyl)-8-methyl-7-nitroquinoline-3-carboxylic acid

Conditions
ConditionsYield
With sulfuric acid In methanol at 20℃; for 0.0833333h;99%
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

4,6-dideuterio-2-methyl-3-nitroaniline
1061566-50-4

4,6-dideuterio-2-methyl-3-nitroaniline

Conditions
ConditionsYield
Stage #1: 3-nitro-o-tolylamine With hydrogenchloride; water-d2 at 180℃; for 0.5h; Microwave irradiation;
Stage #2: With sodium hydroxide In diethyl ether; water regioselective reaction;		97%
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

2-(2-chlorobenzylideneamino)-6-nitrotoluene
128422-36-6

2-(2-chlorobenzylideneamino)-6-nitrotoluene

Conditions
ConditionsYield
In ethanol for 5h; Heating;96%
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

4,6-dibromo-2-methyl-3-nitro-aniline
117824-52-9

4,6-dibromo-2-methyl-3-nitro-aniline

Conditions
ConditionsYield
With benzyltrimethylammonium tribromide; calcium carbonate In methanol; dichloromethane for 0.5h; Ambient temperature;95%
With bromine In acetic acid for 1h; heated on a steam bath;84%
With bromine; acetic acid
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

N-(2-methyl-3-nitrophenyl)ethoxymethylenimine
115118-93-9

N-(2-methyl-3-nitrophenyl)ethoxymethylenimine

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 120℃; for 1h;94%
With sodium hydrogen tartrate at 102℃; for 2h; Time;90.84%
With toluene-4-sulfonic acid at 120℃; for 1h; Claisen Condensation;88%
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

2-iodo-6-nitrotoluene
41252-98-6

2-iodo-6-nitrotoluene

Conditions
ConditionsYield
diazotization;93%
Stage #1: 3-nitro-o-tolylamine With sulfuric acid; sodium nitrite at 0 - 20℃; for 2h;
Stage #2: With potassium iodide at 20℃; for 12h; Further stages.;		91%
Stage #1: 3-nitro-o-tolylamine With sulfuric acid; sodium nitrite In water; acetonitrile at -7 - -5℃; Inert atmosphere;
Stage #2: With potassium iodide In water; acetonitrile at 0 - 20℃; for 0.333333h; Inert atmosphere;		88%
phthalic anhydride
85-44-9

phthalic anhydride

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

N-(2-methyl-3-nitrophenyl)phthalimide

N-(2-methyl-3-nitrophenyl)phthalimide

Conditions
ConditionsYield
With acetic acid for 5h; Condensation; Heating;92.5%
In pyridine
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

N-(2-methyl-3-nitro-phenyl)-acetimidic acid ethyl ester
133053-71-1

N-(2-methyl-3-nitro-phenyl)-acetimidic acid ethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 120℃;92%
With toluene-4-sulfonic acid at 120℃; for 1h;73%
With toluene-4-sulfonic acid at 120℃; for 1h;
maleic anhydride
108-31-6

maleic anhydride

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

N-(2-methyl-3-nitrophenyl)maleamic acid
221279-43-2

N-(2-methyl-3-nitrophenyl)maleamic acid

Conditions
ConditionsYield
In diethyl ether at 20℃;92%
In diethyl ether for 60h;91%
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

2-bromo-6-nitrotoluene
55289-35-5

2-bromo-6-nitrotoluene

Conditions
ConditionsYield
Stage #1: 3-nitro-o-tolylamine With hydrogen bromide for 0.333333h; Heating;
Stage #2: With sodium nitrite at 0 - 5℃; for 0.25h;
Stage #3: With hydrogen bromide; copper(I) bromide at 100℃; for 0.333333h;		90%
Stage #1: 3-nitro-o-tolylamine With hydrogen bromide In water for 0.166667h; Reflux;
Stage #2: With sodium nitrite In water at 0 - 5℃; for 0.5h;
Stage #3: With copper(I) bromide In water at 20 - 70℃; for 1.5h;		89%
Stage #1: 3-nitro-o-tolylamine With hydrogen bromide; sodium nitrite In water at 0 - 5℃; for 0.333333 - 0.5h; Sandmeyer Reaction; Reflux;
Stage #2: With hydrogen bromide; copper(I) bromide In water at 30 - 35℃; for 0.5h; Sandmeyer Reaction; Reflux;		84%
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

N-(2-methyl-3-nitrophenyl)methanesulfonamide
80259-07-0

N-(2-methyl-3-nitrophenyl)methanesulfonamide

Conditions
ConditionsYield
With pyridine at 20℃; for 16h;90%
With pyridine at 20℃; for 2h;
In pyridine
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

benzoyl chloride
98-88-4

benzoyl chloride

N-(2-methyl-3-nitrophenyl)-benzamide
133053-84-6

N-(2-methyl-3-nitrophenyl)-benzamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;89%
With pyridine for 0.5h; Ambient temperature;78%
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

ethyl N-(2-methyl-3-nitrophenyl)formimidate
115118-93-9

ethyl N-(2-methyl-3-nitrophenyl)formimidate

Conditions
ConditionsYield
With toluene-4-sulfonic acid89%
With toluene-4-sulfonic acid Yield given;
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

Triethyl orthopropionate
115-80-0

Triethyl orthopropionate

ethyl N-(2-methyl-3-nitrophenyl)proponimidate
87885-86-7

ethyl N-(2-methyl-3-nitrophenyl)proponimidate

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 120℃; for 1h;89%
acetic anhydride
108-24-7

acetic anhydride

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

1-(4-nitro-1H-indazol-1-yl)ethan-1-one
86009-37-2

1-(4-nitro-1H-indazol-1-yl)ethan-1-one

Conditions
ConditionsYield
Stage #1: 3-nitro-o-tolylamine With potassium acetate In chloroform at 20℃;
Stage #2: acetic anhydride In chloroform at 0 - 40℃;
Stage #3: With isopentyl nitrite In chloroform Reflux;		89%
Stage #1: acetic anhydride; 3-nitro-o-tolylamine With potassium acetate In toluene at 25℃; for 0.25h; Inert atmosphere;
Stage #2: With isopentyl nitrite In toluene at 25℃; Inert atmosphere; Reflux;		60%
Stage #1: acetic anhydride; 3-nitro-o-tolylamine With potassium acetate In toluene at 20℃;
Stage #2: With isopentyl nitrite Reflux;
2-acetylpropanoic acid ethyl ester
609-14-3

2-acetylpropanoic acid ethyl ester

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

ethyl 2-[(2-methyl-3-nitrophenyl)hydrazono]propanoate

ethyl 2-[(2-methyl-3-nitrophenyl)hydrazono]propanoate

Conditions
ConditionsYield
Stage #1: 3-nitro-o-tolylamine With hydrogenchloride; sodium nitrite In water; acetonitrile at -10 - -5℃; for 0.5h;
Stage #2: 2-acetylpropanoic acid ethyl ester With potassium hydroxide In ethanol; water; acetonitrile at -6 - 2℃; for 0.166667h;
Stage #3: With hydrogenchloride In ethanol; water; acetonitrile at 0℃; for 1h;		88%
With hydrogenchloride; sodium nitrite Multistep reaction;
4-(3-(allyloxy)-4-fluorophenoxy)benzaldehyde
862374-44-5

4-(3-(allyloxy)-4-fluorophenoxy)benzaldehyde

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

N-(4-(3-(allyloxy)-4-fluorophenoxy)benzyl)-N-(2-methyl-3-nitrophenyl)amine
448957-16-2

N-(4-(3-(allyloxy)-4-fluorophenoxy)benzyl)-N-(2-methyl-3-nitrophenyl)amine

Conditions
ConditionsYield
Stage #1: 4-(3-(allyloxy)-4-fluorophenoxy)benzaldehyde; 3-nitro-o-tolylamine With acetic acid In dichloromethane at 20℃; for 4h;
Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 12h;		88%
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

1,2-bis(2-methyl-3-nitrophenyl)disulfane
56682-03-2

1,2-bis(2-methyl-3-nitrophenyl)disulfane

Conditions
ConditionsYield
Stage #1: 3-nitro-o-tolylamine With tetrafluoroboric acid; sodium nitrite In water; acetone at -20 - 0℃; for 0.333333h;
Stage #2: With carbon disulfide; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate In dimethyl sulfoxide at 20℃; for 6h; Irradiation;		88%
Multi-step reaction with 2 steps
1: (i) (diazotization), (ii) /BRN= 3561118/, KSCN
2: NH3 / ethanol
View Scheme
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

dimethyl 2-(2-methyl-3-nitrophenylamino)-2-butenedioate
52979-48-3

dimethyl 2-(2-methyl-3-nitrophenylamino)-2-butenedioate

Conditions
ConditionsYield
In methanol at 20℃; for 2h;88%
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

4-bromo-2-methyl-3-nitroaniline
414868-82-9

4-bromo-2-methyl-3-nitroaniline

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile at 0℃; for 0.5h;88%
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

N-benzyl-2-methyl-3-nitroaniline
375856-45-4

N-benzyl-2-methyl-3-nitroaniline

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; benzaldehyde In 1,1-dichloroethane; acetic acid87%
Multi-step reaction with 2 steps
1: AcOH / 1,2-dichloro-ethane / 20 °C
2: Na(OAc)3BH / 1,2-dichloro-ethane
View Scheme
Multi-step reaction with 2 steps
1: AcOH / 1,2-dichloro-ethane / 4 h / 20 °C
2: Na(OAc)3BH / 1,2-dichloro-ethane / 12 h
View Scheme
formaldehyd
50-00-0

formaldehyd

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

(rac)-4,10-dimethyl-3,9-dinitro-5,11-methano-6H,12H-dibenzo[b,f][1,5]diazocine
1142382-04-4

(rac)-4,10-dimethyl-3,9-dinitro-5,11-methano-6H,12H-dibenzo[b,f][1,5]diazocine

Conditions
ConditionsYield
In trifluoroacetic acid at 20℃; for 48h;87%
With trifluoroacetic acid for 48h;87%
With trifluoroacetic acid at 20℃; for 48h;85%
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

4-Chlorobutanoyl chloride
4635-59-0

4-Chlorobutanoyl chloride

4-chloro-N-(2-methyl-3-nitrophenyl)-butyramide
133053-93-7

4-chloro-N-(2-methyl-3-nitrophenyl)-butyramide

Conditions
ConditionsYield
With pyridine In diethyl ether for 3h;86%
benzyl bromide
100-39-0

benzyl bromide

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

N,N-dibenzyl-N-(2-methyl-3-nitrophenyl)amine
448956-36-3

N,N-dibenzyl-N-(2-methyl-3-nitrophenyl)amine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide86%
formaldehyd
50-00-0

formaldehyd

aminocoumarine
1635-31-0

aminocoumarine

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

dimethyl 1-(2-methyl-3-nitrophenyl)-3-(2-oxo-2H-chromen-3-yl)-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate

dimethyl 1-(2-methyl-3-nitrophenyl)-3-(2-oxo-2H-chromen-3-yl)-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 3h; Reflux;86%
...Expand
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

dimedone
126-81-8

dimedone

C15H18N2O3

C15H18N2O3

Conditions
ConditionsYield
With melamine-formaldehyde resin supported H+ In neat (no solvent) at 80℃; for 0.133333h;84%

2-Methyl-3-nitroaniline Chemical Properties

IUPAC Name: 2-Methyl-3-nitroaniline
Product Name: 2-Methyl-3-nitroaniline
The MF of 2-Methyl-3-nitroaniline (CAS NO.603-83-8) is C7H8N2O2.

                              
The MW of 2-Methyl-3-nitroaniline (CAS NO.603-83-8) is 152.15.
Synonyms of 2-Methyl-3-nitroaniline (CAS NO.603-83-8): 2-Methyl-3-aminonitrobenzene ; 2-Methyl-3-nitroaniline ; 3-Nitro-o-toluidine ; Benzenamine, 2-methyl-3-nitro- (9CI) ; o-Toluidine, 3-nitro- ; 2-Amino-6-nitrotoluene 
Product Categories: Intermediates of Dyes and Pigments;Benzene derivatives;Anilines, Aromatic Amines and Nitro Compounds;API intermediates;Drug Intermediates
Form: Yellow rhombic needles (from water) or bright yellow powder
Water Solubility: <0.1 g/100 mL at 23 ºC
Index of Refraction: 1.615 
EINECS: 210-059-6
Density: 1.269 g/ml 
Flash Point: 138.1 °C
Boiling Point: 304.7 °C
Melting Point: 88-91 °C
BRN: 388393

2-Methyl-3-nitroaniline Uses

  2-Methyl-3-nitroaniline (CAS NO.603-83-8) is mainly used for cotton dyeing and printing of color reagent.

2-Methyl-3-nitroaniline Safety Profile

Safety information of 2-Methyl-3-nitroaniline (CAS NO.603-83-8):
Hazard Codes  ToxicT,DangerousN
Risk Statements 
23/24/25 Toxic by inhalation, in contact with skin and if swallowed
33 Danger of cumulative effects
51/53 Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements 
28 After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
36/37 Wear suitable protective clothing and gloves
45 In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
61 Avoid release to the environment. Refer to special instructions safety data sheet
RIDADR  UN 2660 6.1/PG 3
WGK Germany  3
RTECS  XU8200000
Hazard Note  Toxic
HazardClass  6.1
PackingGroup  III
HS Code  29214300

2-Methyl-3-nitroaniline Specification

2-Methyl-3-nitroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizers.

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