Methyl 3-methyl-2-nitrobenzoate Chemical Properties

Melting point:

72-73°C

Boiling point:

286.3±20.0 °C(Predicted)

Density 

1?+-.0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

Solid

color 

White to Almost white

InChI

InChI=1S/C9H9NO4/c1-6-4-3-5-7(9(11)14-2)8(6)10(12)13/h3-5H,1-2H3

InChIKey

NJHDBIXFFZVJGZ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

5471-82-9(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 3-methyl-2-nitro-, methyl ester (5471-82-9)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29163990

Methyl 3-methyl-2-nitrobenzoate Usage And Synthesis

Chemical Properties

Light brown crystalline powder

Uses

Methyl 3-methyl-2-nitrobenzoate is used as a raw material for the synthesis of pesticide intermediate 2-amino-5-chloro-N,3-dimethylbenzamide, and is hydrogenated to produce 2-amino-3-methylbenzoic acid methyl ester.

Synthesis

Acetyl chloride (20 mL) was slowly added dropwise to a suspension of commercially available 3-methyl-2-nitrobenzoic acid (13.45 g, 74.25 mmol) in methanol (200 mL) at 0 °C. The reaction mixture was then heated to reflux temperature with continuous stirring for 20 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate (800 mL) and washed sequentially with saturated aqueous NaHCO3 (200 mL) and brine (150 mL). The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford methyl 3-methyl-2-nitrobenzoate as a white solid (12.35 g, 85% yield). The product was characterized by 1H NMR (CDCl3): δ 2.36 (s, 3H), 3.89 (s, 3H), 7.40-7.51 (m, 2H), 7.84 (m, 1H).

References

[1] Tetrahedron, 2013, vol. 69, # 32, p. 6679 - 6686
[2] Tetrahedron, 2004, vol. 60, # 10, p. 2235 - 2246
[3] Patent: WO2005/66136, 2005, A1. Location in patent: Page/Page column 87-88
[4] Patent: CN106467513, 2017, A. Location in patent: Paragraph 0009; 0036; 0037; 0038; 0039
[5] Chemische Berichte, 1907, vol. 40, p. 4413

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