2-BROMOMETHYL-4-NITRO-BENZOIC ACID METHYL ESTER Chemical Properties

Boiling point:

398.4±37.0 °C(Predicted)

Density 

1.624±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

color 

Off-white

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-43

Safety Statements 

36/37

HS Code 

2916310090

2-BROMOMETHYL-4-NITRO-BENZOIC ACID METHYL ESTER Usage And Synthesis

Uses

Methyl 2-(Bromomethyl)-4-nitrobenzoate is used in the synthetic preparation of cyclic hydroxamic acid derivatives as histone deacetylase inhibitors with antitumor activity.

Synthesis

General procedure for the synthesis of methyl 2-(bromomethyl)-4-nitrobenzoate from methyl 2-methyl-4-nitrobenzoate: methyl 2-methyl-4-nitrobenzoate (20 g, 88.01 mmol) was dissolved in carbon tetrachloride (100 mL) in a 500 mL three-necked round-bottomed flask. Subsequently, N-bromosuccinimide (39.16 g, 220.03 mmol) and azobisisobutyronitrile (AIBN, 2.16 g, 13.20 mmol) were added, and the reaction mixture was heated to reflux for 20 hours. Upon completion of the reaction, the reaction was quenched with distilled water (500 mL) and extracted with dichloromethane (200 mL x 3). The organic layers were combined, washed with saturated brine solution and dried over anhydrous sodium sulfate. The organic layers were concentrated under reduced pressure and the crude product obtained was purified by silica gel column chromatography to afford pure methyl 2-(bromomethyl)-4-nitrobenzoate (19 g, 78.7% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 8.52 (s, 1H), 8.27-8.30 (dd, 1H), 8.07-8.10 (d, 1H), 5.10 (s, 2H), 3.94 (s, 3H).

References

[1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 22, p. 7625 - 7651
[2] Patent: WO2010/139953, 2010, A1. Location in patent: Page/Page column 32
[3] Patent: US2012/115862, 2012, A1. Location in patent: Page/Page column 34-35
[4] Patent: WO2016/81464, 2016, A1. Location in patent: Paragraph 00118
[5] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 3, p. 250 - 255

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