METHYL 2-AMINO-5-BROMO-3-METHYLBENZENECARBOXYLATE Chemical Properties

Melting point:

56-58

Boiling point:

307.3±37.0 °C(Predicted)

Density 

1.506

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

1.61±0.10(Predicted)

Appearance

Light yellow to brown Solid

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933399990

METHYL 2-AMINO-5-BROMO-3-METHYLBENZENECARBOXYLATE Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 2-amino-5-bromo-3-methylbenzoate from methyl 2-amino-3-methylbenzoate: Methyl 2-amino-3-methylbenzoate (142.1 g, 0.843 mol, purity: 98%, quantitative NMR) was dissolved in 240 mL of water, and hydrogen bromide (48% aqueous solution, 149.2 g, 0.885 mol). Subsequently, the resulting suspension was mixed with hydrogen peroxide (30% aqueous solution, 105.1 g, 0.927 mol), and the acceleration of the drop was controlled so that the reaction was completed within 2 h and the reaction temperature was kept lower than 70°C. The reaction mixture was continued to be stirred for 1 h. After the reaction mixture had continued to be stirred for 1 h, sodium bisulphite (39% aqueous solution, 33.7 g, 0.126 mol) was added in batches until the test for peroxide was negative . The pH of the reaction mixture was adjusted to 7-8 with sodium carbonate (0.1 equiv, 9.0 g, 0.084 mol) in batches. after filtration and vacuum drying, methyl 2-amino-5-bromo-3-methylbenzoate was obtained as a light brown solid. Yield: 204.2 g, yield: 97.7%, purity: 98.5% (quantitative NMR).1H NMR (600 MHz, d6-DMSO): δ= 7.70 (d, 1H), 7.36 (pt, 1H), 6.63 (br s, 2H), 3.80 (s, 3H), 2.12 (s, 3H).

References

[1] Patent: US2014/148611, 2014, A1. Location in patent: Paragraph 0066; 0067; 0068
[2] Helvetica Chimica Acta, 2004, vol. 87, # 6, p. 1333 - 1356
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 3, p. 1156 - 1162
[4] Patent: US2015/111870, 2015, A1. Location in patent: Paragraph 0687; 0688
[5] Patent: WO2018/49328, 2018, A1. Location in patent: Page/Page column 26; 27; 28

METHYL 2-AMINO-5-BROMO-3-METHYLBENZENECARBOXYLATE(206548-14-3)Related Product Information

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