Methyl 3-hydroxy-4-nitrobenzoate Chemical Properties

Melting point:

90-91°C

Boiling point:

346.4±27.0 °C(Predicted)

Density 

1.432±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

6.05±0.13(Predicted)

color 

Light yellow to Amber to Dark green

BRN 

2583832

CAS DataBase Reference

713-52-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2918290090

MSDS

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Methyl 3-hydroxy-4-nitrobenzoate Usage And Synthesis

Application

Methyl 3-hydroxy-4-nitrobenzoate is an organic intermediate that can be obtained by esterification of 3-hydroxy-4-nitrobenzoic acid. It can be used as an organic synthesis intermediate and a pharmaceutical intermediate, and is mainly used in laboratory research and development processes and chemical production processes.

Synthesis

Concentrated sulfuric acid (0.5 mL) was slowly added dropwise to a solution of 3-hydroxy-4-nitrobenzoic acid (1.88 g, 10.3 mmol) dissolved in undried HPLC-grade methanol (60 mL), and the reaction mixture was subsequently heated to reflux for 18 hours. Upon completion of the reaction, sodium bicarbonate was added to the reaction solution to neutralize the acidity, followed by evaporation of the solvent under reduced pressure. To the residue, water and ethyl acetate were added for extraction and the aqueous layer was separated. The aqueous layer was further extracted five times with ethyl acetate. All organic layers were combined, washed twice with saturated brine, dried over anhydrous magnesium sulfate, and finally concentrated under reduced pressure to remove the solvent to give methyl 3-hydroxy-4-nitrobenzoate as yellow crystals with a yield of 2.00 g (99% yield) and a melting point of 89.5-90.5°C (literature values: 86-88°C, 91-92°C). UV spectrum (methanol): λmax = 238, 270, 351 nm. infrared spectrum (ATR): ν = 3310, 3124, 3050, 2962, 2842, 1720, 1622, 1587, 1521, 1476, 1434, 1323, 1283, 1222, 1147, 1098, 1067, 967, 891, 843, 798, 780, 743, 666 cm-1.1H NMR (500 MHz, CDCl3): δ=3.96 (s, 3H), 7.61 (dd, J=8.8, 1.7 Hz, 1H), 7.83 (d, J=1.7 Hz, 1H), 8.17 (d, J=8.8 Hz, 1H), 10.50 (s , 1H).13C NMR and DEPT (125 MHz, CDCl3): δ = 53.08 (CH3), 120.73 (CH), 121.80 (CH), 125.41 (CH), 135.90 (C), 138.10 (C), 154.79 (C), 164.97 (C=O). Mass spectrum (ESI, -10V): m/z=196 ([M-H]-). Calculated elemental analysis (C8H7NO5): C 48.74%, H 3.58%, N 7.10%; measured values: C 48.58%, H 3.44%, N 7.25%.

References

[1] Synlett, 2008, # 11, p. 1698 - 1702
[2] Organic and Biomolecular Chemistry, 2012, vol. 10, # 15, p. 2928 - 2933
[3] Synlett, 2015, vol. 26, # 9, p. 1175 - 1178
[4] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8219 - 8248
[5] Tetrahedron, 2012, vol. 68, # 33, p. 6727 - 6736

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