Methyl 3-bromo-5-nitrobenzoate Chemical Properties

Melting point:

70 °C(Solv: ethanol (64-17-5))

Boiling point:

326.0±22.0 °C(Predicted)

Density 

1.673±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

color 

Off-white to light brown

InChI

InChI=1S/C8H6BrNO4/c1-14-8(11)5-2-6(9)4-7(3-5)10(12)13/h2-4H,1H3

InChIKey

DDJCZBFPZLYREP-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2916399090

Methyl 3-bromo-5-nitrobenzoate Usage And Synthesis

Uses

Methyl 3-bromo-5-nitrobenzoate is a pharmaceutical intermediate. Methyl 3-bromo-5-nitrobenzoate can be used to prepare 3-amidobenzoic acid derivatives such as 3-(4-trifluoromethylbenzoyl)amino-5-(2',6'-(2H)piperidinylphenyl)benzoic acid, which have P2Y receptor antagonist effects.

Synthesis

The preparation method is achieved through a two-step reaction: first, at 0°C, 3-nitrobenzoic acid is dissolved in concentrated sulfuric acid, N-bromosuccinimide is added, the reaction is carried out at 65°C for 2 hours, and 3-nitro-5-bromobenzoic acid is obtained after stirring with ice water, suction filtration, and drying, with a yield of 95%. Next, the product is dissolved in methanol, SOCl₂ is added dropwise at 0°C, the reaction is carried out at room temperature for 2 hours, and Methyl 3-bromo-5-nitrobenzoate is finally obtained after treatment with a sodium bicarbonate solution, extraction with ethyl acetate, drying, and column chromatography purification, with a yield of 86.46%.

References

[1] Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4764 - 4774
[2] Journal of the American Chemical Society, 2013, vol. 135, # 46, p. 17408 - 17416
[3] Patent: WO2014/19685, 2014, A1. Location in patent: Page/Page column 13; 39
[4] Journal of Molecular Structure, 2013, vol. 1036, p. 505 - 509
[5] Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 3496 - 3505

Methyl 3-bromo-5-nitrobenzoate(6307-87-5)Related Product Information

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