| Identification | More | [Name]
2-Methyl-6-nitroaniline | [CAS]
570-24-1 | [Synonyms]
2-AMINO-1-METHYL-3-NITROBENZENE
2-AMINO-3-NITROTOLUENE
2-METHYL-6-NITROANILINE
2-METHYL-6-NITROBENZENAMINE
2-NITRO-6-METHYLANILINE
3-NITRO-2-AMINOTOLUENE
6-NITRO-O-TOLUIDINE
LABOTEST-BB LTBB000621
2-Amino-3-methylnitrobenzene
6-Nitro-o-toluidine(2-Methyl-6-nitroaniline)
Benzenamine, 2-methyl-6-nitro-
2-Amino-3-nitrotoluene~6-Nitro-o-toluidine
2-Methyl-6-nitroaniline,(2-Amino-3-nitrotoluene
6-Nitro-2-Methylaniline
6-Nitro-o-tol
Methylnitroaniline, 99%
2-Methyl-6-nitro-phenylamine
2-METHYL-6-NITROANILINE OEKANAL, 250 MG
1-AMINO-2-METHYL-6-NITROBENZENE
6-NITRO-ORTHO-TOLUIDINE | [EINECS(EC#)]
209-329-6 | [Molecular Formula]
C7H8N2O2 | [MDL Number]
MFCD00007744 | [Molecular Weight]
152.15 | [MOL File]
570-24-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Redish-Brown Solid | [Melting point ]
93-96 °C (lit.) | [Boiling point ]
124 °C / 1mmHg | [density ]
1.19 g/cm3 | [refractive index ]
1.6276 (estimate) | [Fp ]
110 °C
| [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
<1mg/l | [form ]
Crystalline Powder | [pka]
-0.44±0.25(Predicted) | [color ]
Brownish | [Water Solubility ]
<0.1 g/100 mL at 23 ºC | [BRN ]
1868029 | [Cosmetics Ingredients Functions]
HAIR DYEING | [InChI]
1S/C7H8N2O2/c1-5-3-2-4-6(7(5)8)9(10)11/h2-4H,8H2,1H3 | [InChIKey]
FCMRHMPITHLLLA-UHFFFAOYSA-N | [SMILES]
Cc1cccc(c1N)[N+]([O-])=O | [CAS DataBase Reference]
570-24-1(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Methyl-6-nitroaniline(570-24-1) | [EPA Substance Registry System]
570-24-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,N,Xi | [Risk Statements ]
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 ]
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 2660 6.1/PG 3
| [WGK Germany ]
3
| [F ]
10 | [Hazard Note ]
Toxic | [HazardClass ]
6.1 | [HazardClass ]
IRRITANT | [PackingGroup ]
Ⅲ | [HS Code ]
29214300 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Dermal
Acute Tox. 3 Inhalation
Acute Tox. 3 Oral
Aquatic Acute 1
Aquatic Chronic 2
STOT RE 2 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
2-METHYLACETANILIDE-->2-Azido-3-nitrotoluene-->o-Oxalotoluidide-->2-Aminotoluene-5-sulfonic acid-->Sulfuric acid-->2-METHYL-4-NITROACETANILIDE-->Acetic anhydride-->N-(2-METHYL-6-NITRO-PHENYL)-ACETAMIDE-->Nitric acid-->4-Methyl-2-nitroaniline | [Preparation Products]
4-(BROMOMETHYL)-2,1,3-BENZOTHIADIAZOLE-->2,1,3-BENZOTHIADIAZOLE-4-CARBOXYLIC ACID-->2,1,3-BENZOTHIADIAZOL-4-YLMETHANOL,97%-->2,1,3-BENZOTHIADIAZOLE-4-CARBALDEHYDE-->1H-INDAZOL-7-AMINE-->7-Nitroindazole-->2-Bromo-3-nitrotoluene-->2,3-DINITROBENZOIC ACID-->4-methyl-1H-benzotriazole-->3-AMINO-2-BROMO-BENZOIC ACID METHYL ESTER-->4-broMo-3-Methylbenzene-1,2-diaMine-->5-BROMO-7-NITRO-1H-INDAZOLE-->METHYL 2-BROMO-3-NITROBENZOATE |
| Hazard Information | Back Directory | [General Description]
Orange-yellow prisms or brown granular powder. | [Reactivity Profile]
2-METHYL-6-NITROANILINE(570-24-1) is incompatible with acids, acid chlorides, acid anhydrides, chloroformates, and strong oxidizers. | [Air & Water Reactions]
This chemical is sensitive to prolonged exposure to air. Insoluble in water. | [Fire Hazard]
Flash point data for this compound are not available, but 2-METHYL-6-NITROANILINE is probably combustible. | [Chemical Properties]
Redish-Brown Solid | [Synthesis]
The general procedure for the synthesis of 2-methyl-6-nitroaniline from 2-methylacetanilide was carried out as follows: the modified Howard method [27] was used. Toluidine (1a or 1b; 53.5 mL, 0.5 mol) was slowly added to acetic anhydride (325 mL) in batches while maintaining constant stirring. The reaction solution was cooled to 12-13 °C in an ice-salt bath. Subsequently, 70% nitric acid (63 mL) was slowly added dropwise to the reaction mixture at a rate that maintained the temperature at 10-12 °C with constant stirring. The dropwise addition process took 2.5 h to complete, after which the solution was poured into 1.5 L of ice water. The resulting acetamide (3a, or a mixture of 3b and 3c) precipitate (as a cream-colored solid) was collected on a Brinell's funnel, washed with four 250 mL portions of ice water, and partially dried by suction. The wetted acetamide (3a, or a mixture of 3b and 3c) was mixed with 70% sulfuric acid (100 mL) and stirred at reflux for 3 hours. The acetamide 3b was separated from the reaction mixture by steam distillation to give the hydrolysis product of 2-methyl-6-nitroaniline (4b). After the distiller was cooled, the isolated bright orange needle-like crystals 4b were collected on a Brinell funnel and dried in a vacuum desiccator. If acetamide 3a was hydrolyzed, the warm reaction mixture was diluted with 350 mL of water and alkalized with 10% aqueous sodium hydroxide. After cooling to room temperature, 4-methyl-2-nitroaniline (4a) precipitated as a brown powder, which was separated by vacuum filtration, washed with three parts of 200 mL of water, and dried in a vacuum desiccator. The yields of compounds 4a and 4b were 53.6% (40.73 g) and 52.3% (39.78 g), respectively. | [References]
[1] Bulletin des Societes Chimiques Belges, 1969, vol. 78, p. 571 - 582
[2] Chemistry Letters, 1989, p. 1849 - 1852
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 13, p. 6047 - 6060
[4] Polyhedron, 2016, vol. 105, p. 137 - 149 |
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