2-Methyl-6-nitroaniline CAS 570-24-1
2-Methyl-6-nitroaniline Basic information
| Product Name: | 2-Methyl-6-nitroaniline |
| Synonyms: | 3-NITRO-2-AMINOTOLUENE;6-NITRO-O-TOLUIDINE;2-METHYL-6-NITROBENZENAMINE;2-METHYL-6-NITROANILINE;2-NITRO-6-METHYLANILINE;2-AMINO-1-METHYL-3-NITROBENZENE;2-AMINO-3-NITROTOLUENE;Benzenamine, 2-methyl-6-nitro- |
| CAS: | 570-24-1 |
| MF: | C7H8N2O2 |
| MW: | 152.15 |
| EINECS: | 209-329-6 |
| Product Categories: | Phenyls & Phenyl-Het;Building Blocks;C7;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Intermediates of Dyes and Pigments;Anilines, Aromatic Amines and Nitro Compounds;Aromatics Compounds;Aromatics;Phenyls & Phenyl-Het;Miscellaneous Reagents;Pharmaceutical intermediates;amine| nitro-compound;Amines;Benzene derivates;API intermediates |
| Mol File: | 570-24-1.mol |
2-Methyl-6-nitroaniline Chemical Properties
| 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 | 2-Methyl-6-nitroaniline (570-24-1) |
Safety Information
| Hazard Codes | T,N,Xi |
| Risk 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 |
| 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 |
| Uses | 2-Methyl-6-nitroaniline is a compound useful in organic synthesis. Dyes and metabolites, Environmental Testing. |
| Chemical Properties | Redish-Brown Solid |
| Uses | 2-Methyl-6-nitroaniline (cas# 570-24-1) is a compound useful in organic synthesis. Dyes and metabolites, Environmental Testing |
| 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. |
| Synthesis | 120-66-1 570-24-1 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 |
2-Methyl-6-nitroaniline Preparation Products And Raw materials
| 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 |
