| Identification | Back Directory | [Name]
3-Methyl-2-nitroaniline | [CAS]
601-87-6 | [Synonyms]
2-NITRO-M-TOLUIDINE
3-AMINO-2-NITROTOLUENE
3-METHYL-2-NITROANILINE
2-NITRO-3-METHYL ANILINE
3-Methyl-2-nitrobenzenamine
3-Methyl-2-nitroaniline 97%
3-Methyl-2-nitro-phenylamine
Benzenamine,3-methyl-2-nitro-
3-Amino-2-nitrotoluene, 2-Amino-6-methylnitrobenzene
3-Amino-2-nitrotoluene, 2-Amino-6-methyl-1-nitrobenzene
3-Amino-2-nitrotoluene, 2-Amino-6-methylnitrobenzene, 2-Nitro-m-toluidine | [Molecular Formula]
C7H8N2O2 | [MDL Number]
MFCD00074851 | [MOL File]
601-87-6.mol | [Molecular Weight]
152.15 |
| Chemical Properties | Back Directory | [Melting point ]
107-108 °C | [Boiling point ]
288.6±20.0 °C(Predicted) | [density ]
1.269±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
crystalline powder | [pka]
-0.11±0.10(Predicted) | [color ]
Orange | [InChI]
InChI=1S/C7H8N2O2/c1-5-3-2-4-6(8)7(5)9(10)11/h2-4H,8H2,1H3 | [InChIKey]
VDCZKCIEXGXCDJ-UHFFFAOYSA-N | [SMILES]
C1(N)=CC=CC(C)=C1[N+]([O-])=O |
| Hazard Information | Back Directory | [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. | [Synthesis]
General procedure for the synthesis of 3-methyl-2-nitroaniline from 3-methyl-2-nitrobenzamide: NaOH (2.220 g, 55.5 mmol) was dissolved in water (12 mL) at 0°C, followed by the addition of Br2 (0.322 mL, 6.26 mmol). Next, 3-methyl-2-nitrobenzamide (1 g, 5.55 mmol) was added all at once and the mixture was slowly heated in a water bath to 50-55°C (internal temperature), at which point oil droplets were observed to separate. The temperature was continued to be gradually increased to 70°C and maintained at this temperature for 1 hour. Subsequently, a solution of NaOH (0.7 g) dissolved in water (4 mL) was added and the temperature was slowly raised to 80°C and held for another 1 hour. After completion of the reaction, it was cooled to room temperature and extracted with EtOAc (3x50mL). The organic layers were combined, dried and concentrated to give 0.7 g (90% yield) of the target compound 3-methyl-2-nitroaniline.LC-MS analysis showed m/z of 153.1 (M + H)+ and retention time of 1.65 min. | [References]
[1] Patent: WO2015/92713, 2015, A1. Location in patent: Page/Page column 73; 74
[2] Patent: WO2016/203400, 2016, A1. Location in patent: Page/Page column 49
[3] Patent: WO2016/203401, 2016, A1. Location in patent: Page/Page column 60; 61
[4] Patent: WO2016/202253, 2016, A1. Location in patent: Page/Page column 126; 127
[5] Patent: WO2018/104766, 2018, A1. Location in patent: Page/Page column 60-61 |
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