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| CAS No.: | 570-24-1 |
|---|---|
| Name: | 2-Methyl-6-nitroaniline |
| Article Data: | 41 |
| Cas Database | |
| Molecular Structure: | |
|
|
|
| Formula: | C7H8N2O2 |
| Molecular Weight: | 152.153 |
| Synonyms: | 1-Amino-2-methyl-6-nitrobenzene;6-Nitro-o-toluidine;2-Amino-3-nitrotoluene;Benzenamine, 2-methyl-6-nitro- (9CI);2-Methyl-6-nitro-benzenamine;Benzenamine, 2-methyl-6-nitro-;2-methyl-6-nitro-aniline;2-Methyl-6-Nitro-toluidine;2-Methyl-6-nitrobenzenamine; |
| EINECS: | 209-329-6 |
| Density: | 1.269 g/cm3 |
| Melting Point: | 93-96 °C(lit.) |
| Boiling Point: | 301.4 °C at 760 mmHg |
| Flash Point: | 136.1 °C |
| Solubility: | <0.1 g/100 mL at 23 °C in water |
| Appearance: | redish-brown solid |
| Hazard Symbols: |
 T,  N,  Xi
|
| Risk Codes: | 23/24/25-33-51/53 |
| Safety: | 28-36/37-45-61-28A |
| Transport Information: | UN 2660 6.1/PG 3 |
| PSA: | 71.84000 |
| LogP: | 2.58980 |
| 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% |
| 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; |
| 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
A
2-Methyl-6-nitroaniline
B
2-methyl-4-nitro-benzenamine
| 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
A
2-Methyl-6-nitroaniline
B
2-methyl-4-nitroacetanilide
| Conditions | Yield |
|---|---|
| With hydrogenchloride | A 46% B n/a |
| Conditions | Yield |
|---|---|
| With acetic acid und Erwaermen des Reaktionsprodukts mit wss.Salzsaeure; |
N-(2-methylphenyl)acetamide
A
2-Methyl-6-nitroaniline
B
2-methyl-4-nitroacetanilide
| Conditions | Yield |
|---|---|
| With nitric acid; acetic anhydride; acetic acid at 15 - 20℃; ueber mehrere Stufen; |
| Conditions | Yield |
|---|---|
| With ammonia at 150 - 160℃; unter Druck; |
N-(2-methyl-6-nitrophenyl)acetamide
sodium methylate
2-Methyl-6-nitroaniline
| Conditions | Yield |
|---|---|
| Rate constant; |
N-(2-methyl-6-nitrophenyl)acetamide
2-Methyl-6-nitroaniline
| Conditions | Yield |
|---|---|
| With sodium methylate | |
| With hydrogenchloride | |
| (hydrolysis); |
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The molecular structure of 2-Methyl-6-nitroaniline (CAS NO.570-24-1):
IUPAC Name: 2-Methyl-6-nitroaniline
Molecular Weight: 152.15062 g/mol
Molecular Formula: C7H8N2O2
Density: 1.269 g/cm3
Melting Point: 93-96 °C(lit.)
Boiling Point: 301.4 °C at 760 mmHg
Flash Point: 136.1 °C
Index of Refraction: 1.615
Molar Refractivity: 41.85 cm3
Molar Volume: 119.8 cm3
Surface Tension: 54.9 dyne/cm
Enthalpy of Vaporization: 54.16 kJ/mol
Vapour Pressure: 0.00105 mmHg at 25 °C
Water Solubility: <0.1 g/100 mL at 23 °C
XLogP3-AA: 2
H-Bond Donor: 1
H-Bond Acceptor: 3
Exact Mass: 152.058578
MonoIsotopic Mass: 152.058578
Topological Polar Surface Area: 69.2
Heavy Atom Count: 11
Canonical SMILES: CC1=C(C(=CC=C1)[N+](=O)[O-])N
InChI: InChI=1S/C7H8N2O2/c1-5-3-2-4-6(7(5)8)9(10)11/h2-4H,8H2,1H3
InChIKey: FCMRHMPITHLLLA-UHFFFAOYSA-N
EINECS: 209-329-6
Product Categories: Intermediates of Dyes and Pigments; Anilines, Aromatic Amines and Nitro Compounds; Amines; Phenyls & Phenyl-Het; Benzene derivates; API intermediates; Aromatics Compounds; Aromatics; Phenyls & Phenyl-Het
2-Methyl-6-nitroaniline (CAS NO.570-24-1) is used in organic synthesis.
Hazard Codes: 
T, 
N, 
Xi
Risk Statements: 23/24/25-33-51/53
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
R33:Danger of cumulative effects.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 28-36/37-45-61-28A
S28:After contact with skin, wash immediately with plenty of soap-suds.
S36/37:Wear suitable protective clothing and gloves.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 2660 6.1/PG 3
WGK Germany: 3
F: 10
Hazard Note: Toxic
HazardClass: IRRITANT
HS Code: 29214300
2-Methyl-6-nitroaniline (CAS NO.570-24-1) is also named as 1-Amino-2-methyl-6-nitrobenzene ; 2-Methyl-6-nitro-benzenamine ; 6-Nitro-o-toluidine ; Benzenamine, 2-methyl-6-nitro- ; NSC 286 . 2-Methyl-6-nitroaniline (CAS NO.570-24-1) is redish-brown solid. It is insoluble in water. 2-Methyl-6-nitroaniline is sensitive to prolonged exposure to air. It is incompatible with acids, acid chlorides, acid anhydrides, chloroformates, and strong oxidizers.Flash point data for 2-Methyl-6-nitroaniline are not available, but it is probably combustible.
