5-BROMO-2-METHYL-3-NITROPHENYL METHYLCARBOXYLATE Chemical Properties

Melting point:

51.0 to 55.0 °C

Boiling point:

329.6±37.0 °C(Predicted)

Density 

1.596±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Light yellow

InChI

InChI=1S/C9H8BrNO4/c1-5-7(9(12)15-2)3-6(10)4-8(5)11(13)14/h3-4H,1-2H3

InChIKey

UPBDNPCJIJAMPI-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2916.39.7900

5-BROMO-2-METHYL-3-NITROPHENYL METHYLCARBOXYLATE Usage And Synthesis

Synthesis

The general procedure for the synthesis of methyl 5-bromo-2-methyl-3-nitrobenzoate from methanol and 2-methyl-3-nitro-5-bromobenzoic acid was as follows: 2-methyl-3-nitro-5-bromobenzoic acid (21.2 g, 81.5 mmol) was dissolved in SOCl2 (100 mL), and the mixture was heated to reflux until it clarified (ca. 1.5 h). After the reaction was complete, the mixture was cooled and concentrated in vacuum. The residue was added to 250 mL of methanol in batches and the resulting mixture was stirred overnight under reflux conditions. Upon completion of the reaction, the mixture was cooled and concentrated. The residue was dissolved in 300 mL of ethyl acetate, washed sequentially with saturated aqueous NaHCO3 and brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography (eluent: petroleum ether:ethyl acetate=20:1, v:v) to afford methyl 5-bromo-2-methyl-3-nitrobenzoate (21.2 g, yield: 95%) as a light yellow solid.

References

[1] Patent: WO2014/18866, 2014, A1. Location in patent: Paragraph 00181; 00183
[2] Patent: US2018/265517, 2018, A1. Location in patent: Paragraph 0318-0321
[3] Patent: US2017/8904, 2017, A1. Location in patent: Paragraph 0422; 0424
[4] Patent: US2018/177750, 2018, A1. Location in patent: Paragraph 1235-1239
[5] Patent: CN105481790, 2016, A. Location in patent: Paragraph 0198; 0199; 0200; 0204

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