Uses
4-Ethyl-3-nitrobenzoic Acid can be useful in the study of defined positive charge patterns created on DNA nanostructures to determine cellular uptake efficiency.
Synthesis
A. Synthesis of 4-ethyl-3-nitrobenzoic acid
Nitric acid (12 mL) was added slowly and dropwise to a suspension of concentrated sulfuric acid (24 mL) of 4-ethylbenzoic acid (4.53 g, 30.16 mmol) at 0 °C. The reaction temperature was maintained at 0 °C with continuous stirring for 1.5 hours. Upon completion of the reaction, the mixture was carefully poured into ice water and a solid was precipitated. The solid product was collected by filtration and washed with cold water and dried to give 4-ethyl-3-nitrobenzoic acid (5.79 g, 98% yield).
Product characterization data: 1H NMR (400 MHz, DMSO-d6) δ 1.23 (3H, t, J = 7.2 Hz), 2.88 (2H, q, J = 7.2 Hz), 7.67 (1H, d, J = 8.0 Hz), 8.15 (1H, dd, J = 1.6, 8.0 Hz), 8.36 (1H, d, J = 1.6 Hz).
References
[1] Patent: WO2014/73904, 2014, A1. Location in patent: Paragraph 1151-1154
[2] Patent: WO2014/89364, 2014, A1. Location in patent: Paragraph 00685; 00686
[3] Langmuir, 2014, vol. 30, # 28, p. 8452 - 8460
[4] Patent: WO2004/46107, 2004, A1. Location in patent: Page 187
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 21, p. 5995 - 6006
