| Identification | More | [Name]
Methyl 5-nitro-2-methylbenzoate | [CAS]
77324-87-9 | [Synonyms]
Methyl 5-nitro-2-methylbenzoate
5-Nitro-o-toluic acid methyl ester
Methyl 2-methyl-5-nitrobenzoate
5-Nitro-o-toluicacidmethylester(COOCH3=1) | [Molecular Formula]
C9H9NO4 | [MDL Number]
MFCD00230865 | [Molecular Weight]
195.17 | [MOL File]
77324-87-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
67.0 to 71.0 °C | [Boiling point ]
305.4±22.0 °C(Predicted) | [density ]
1?+-.0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [color ]
Light orange to Yellow to Green | [CAS DataBase Reference]
77324-87-9(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White crystalline powder | [Synthesis]
4.2.1 Synthesis of methyl 2-methyl-5-nitrobenzoate (2): 2-methyl-5-nitrobenzoic acid (15 g, 82.8 mmol) and potassium carbonate (K2CO3, 17.2 g, 124.2 mmol) were suspended in N,N-dimethylformamide (DMF, 75 mL) in a dry round-bottom flask. To this suspension, iodomethane (6.7 mL) was slowly added dropwise at room temperature. The reaction mixture was stirred at room temperature overnight (~12 hours). After completion of the reaction, the mixture was poured into water (500 mL) and the aqueous phase was extracted three times with ethyl acetate (EA). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give methyl 2-methyl-5-nitrobenzoate (15.3 g, 94% yield) as a yellow solid. The product was confirmed by 1H NMR (400 MHz, CDCl3): δ 8.52 (s, 1H), 8.05 (s, 1H), 7.30 (s, 1H), 3.83 (s, 3H), 2.56 (s, 3H). ESI-MS analysis showed m/z 196 [M + H]+. | [References]
[1] Journal of the American Chemical Society, 2003, vol. 125, # 40, p. 12074 - 12075
[2] Patent: US6344465, 2002, B1. Location in patent: Page column 32
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5881 - 5890
[4] Patent: US2005/43385, 2005, A1. Location in patent: Page/Page column 14
[5] Patent: US2001/34343, 2001, A1 |
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