| Identification | Back Directory | [Name]
2-CARBOXY-3-ETHYL NITROBENZOATE | [CAS]
16533-45-2 | [Synonyms]
1-Ethyl-3-nitrophthalate
2-CARBOXY-3-ETHYL NITROBENZOATE
2-carboxy-3-nitrobenzoate ethyl ester
2-(Ethoxycarbonyl)-6-nitrobenzoic acid
2-Carboxy-3-nitrobenzoic acid ethyl ester
2-(Ethoxycarbonyl)-6-nitrobenzoic Acid 2-
1,2-Benzenedicarboxylic acid, 3-nitro-, 1-ethyl ester | [Molecular Formula]
C10H9NO6 | [MDL Number]
MFCD01365751 | [MOL File]
16533-45-2.mol | [Molecular Weight]
239.18 |
| Chemical Properties | Back Directory | [Melting point ]
157℃ | [Boiling point ]
415.5±35.0 °C(Predicted) | [density ]
1.421±0.06 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
1.90±0.30(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C10H9NO6/c1-2-17-10(14)6-4-3-5-7(11(15)16)8(6)9(12)13/h3-5H,2H2,1H3,(H,12,13) | [InChIKey]
SZAOZGFHEAVFMM-UHFFFAOYSA-N | [SMILES]
C1(C(OCC)=O)=CC=CC([N+]([O-])=O)=C1C(O)=O |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white crystalline powder | [Synthesis]
The general procedure for the synthesis of ethyl 2-carboxy-3-nitrobenzoate from 3-nitrophthalic acid is as follows: 3-nitrophthalic acid (35 g) was dissolved in ethanol (300 ml) containing concentrated hydrochloric acid. Sulfuric acid (20 ml) was slowly added to this solution and the reaction was then heated under reflux conditions for 24 hours. After completion of the reaction, the solvent was removed by distillation. The residue was poured into ice water (700 ml) and extracted with ethyl acetate. The organic layer was washed with water and back-extracted with aqueous potassium carbonate. The aqueous layer was acidified to acidity with hydrochloric acid and extracted with dichloromethane. The organic layer was washed with water and dried. Finally, the solvent was removed by distillation to afford the solid product ethyl 2-carboxy-3-nitrobenzoate (29 g, 74% yield), which could be used in subsequent reactions without further purification. The structure of the product was confirmed by 1H-NMR (90 MHz, CDCl3) and IR (Nujol): 1H-NMR δ: 1.43 (3H, t), 4.47 (2H, q), 7.70 (1H, t), 8.40 (2H, d), 9.87 (1H, br s); IR (Nujol) cm-1: 1725,1535, 1350,1300,1270. | [References]
[1] Patent: US5128356, 1992, A
[2] Patent: US5196444, 1993, A |
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