Methyl 2-bromo-5-nitrobenzoate Chemical Properties

Melting point:

79-81 °C (lit.)

Boiling point:

326.7±22.0 °C(Predicted)

Density 

1.673±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, DCM. Ethyl Acetate

form 

Crystalline Powder

color 

Yellow

BRN 

2617575

CAS DataBase Reference

6942-36-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Methyl 2-bromo-5-nitrobenzoate Usage And Synthesis

Chemical Properties

yellow crystalline powder

Uses

Methyl 2-bromo-5-nitrobenzoate may be used in chemical synthesis.

Synthesis

Methyl 2-bromo-5-nitrobenzoate was synthesized by esterification reaction using methanol and 2-bromo-5-nitrobenzoic acid as raw materials. The specific steps are as follows: in a dry reaction flask, 2-bromo-5-nitrobenzoic acid was dissolved in an appropriate amount of methanol, and a catalytic amount of concentrated sulfuric acid was added. The reaction mixture was stirred under reflux conditions for 6 hours. Upon completion of the reaction, the mixture was cooled to room temperature, poured into ice water and neutralized with sodium bicarbonate solution to pH=7. Subsequently, the product was extracted with dichloromethane, the organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=10:1) to afford methyl 2-bromo-5-nitrobenzoate in white crystalline form in 81% yield. The structure of the product was confirmed by 1H NMR and 13C NMR: 1H NMR (400 MHz, CDCl3) δ 4.00 (s, 3H), 7.88 (d, J = 8.76 Hz, 1H), 8.18 (dd, J = 2.76 Hz, 1H), 8.66 (d, J = 2.74 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 53.12, 126.33, 126.61, 129.24, 133.12, 135.71, 146.70, 164.48.

References

[1] Journal of the American Chemical Society,
[2] Journal of the American Chemical Society, 2009, vol. 131, p. 54 - 55
[3] Synthesis, 1999, # 7, p. 1246 - 1250
[4] Patent: US2009/131527, 2009, A1. Location in patent: Page/Page column 8
[5] Tetrahedron Letters, 2012, vol. 53, # 46, p. 6245 - 6249,5

Methyl 2-bromo-5-nitrobenzoate(6942-36-5)Related Product Information

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