2-Methyl-4-nitrobenzoic acid Chemical Properties

Melting point:

150-154 °C (lit.)

Boiling point:

153 °C

Density 

1.392±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

pK1:1.86 (25°C)

color 

Pale Yellow to Yellow

InChI

InChI=1S/C8H7NO4/c1-5-4-6(9(12)13)2-3-7(5)8(10)11/h2-4H,1H3,(H,10,11)

InChIKey

XXXOBNJIIZQSPT-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C([N+]([O-])=O)C=C1C

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-43

Safety Statements 

37/39

WGK Germany 

3

HS Code 

29163100

2-Methyl-4-nitrobenzoic acid Usage And Synthesis

Uses

2-Methyl-4-nitrobenzoic acid is used as a reagent to synthesize amino-1H-pyrazole amide derivatives, compounds that act as Raf kinase inhibitors in melanoma cells. 2-Methyl-4-nitrobenzoic acid is also used as a reagent to synthesize fluorogenic substrates, compounds that can be used for activity imaging within living cells.

Synthesis

The general procedure for the synthesis of 2-methyl-4-nitrobenzoic acid from 4-nitrophthalic acid is as follows: in a 50 mL three-necked round-bottomed flask equipped with a magnetic stirrer and reflux condenser, 4-nitrophthalic acid (0.15 g, 1 mmol), N-hydroxyphthalimide (NHPI, 0.05 g, 0.3 mmol), 40% nitric acid (1.26 g, 8 mmol), cobalt chloride hexahydrate (CoCl2-6H2O, 7.1 mg, 0.03 mmol), manganese acetate tetrahydrate (Mn(OA)), and cobalt chloride hexahydrate (CoCl2-6H2O). , 8 mmol), cobalt chloride hexahydrate (CoCl2-6H2O, 7.1 mg, 0.03 mmol), manganese acetate tetrahydrate (Mn(OAc)2-4H2O, 7.1 mg, 0.03 mmol), and phase transfer catalyst (0.04 mmol). The reaction mixture was heated to reflux at atmospheric pressure for 12 hours. After completion of the reaction, it was cooled to room temperature and washed with 10 mL of water. The aqueous phase was extracted with ethyl acetate (3 x 5 mL), the organic phases were combined and dried over anhydrous sodium sulfate. Ethyl acetate was removed from the organic phase by rotary evaporation and the crude product was quantified by HPLC analysis based on an internal standard (2,4-dinitrotoluene). The crude product was recrystallized by ethanol/water (3:1) to afford white acicular crystals of 2-methyl-4-nitrobenzoic acid (0.13 g, 72% yield) with melting point 151-152°C. IR (KBr) ν/cm-1 : 1702 (C=O).1H NMR (CDCl3, 500 MHz) δ: 2.79 (s, 3H, CH3), 8.13- 8.17 (m, 2H, Ar-H), 8.21 (d, 1H, J=6.8Hz, Ar-H). The by-product 4-nitrophthalic acid was separated by column chromatography (ethyl acetate/hexane, 1:5) to give light-colored acicular crystals with a melting point of 163°C. IR (KBr) ν/cm-1 : 1730, 1677 (C=O).1H NMR (CDCl3, 500MHz) δ: 7.86 (d, J=8.6Hz, 1H, Ar-H), 8.36 ( dd, J1=8.6Hz, J2=2.0Hz, 1H, Ar-H), 8.42 (d, J=2.0Hz, 1H, Ar-H).

References

[1] Chemical Papers, 2015, vol. 69, # 4, p. 580 - 585
[2] Patent: CN106995374, 2017, A. Location in patent: Paragraph 0043; 0044; 0045; 0046; 0047; 0048; 0049-0057
[3] Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 8092 - 8103
[4] Patent: CN105777565, 2016, A. Location in patent: Paragraph 0006

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