METHYL 2-BROMO-4-NITROBENZOATE Chemical Properties

Melting point:

82.0 to 86.0 °C

Boiling point:

339.2±27.0 °C(Predicted)

Density 

1.673±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

Light orange to Yellow to Green

InChI

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

InChIKey

XYMZAFDNPJLOTP-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C([N+]([O-])=O)C=C1Br

CAS DataBase Reference

100959-22-6(CAS DataBase Reference)

Safety Information

HS Code 

2916399090

METHYL 2-BROMO-4-NITROBENZOATE Usage And Synthesis

Synthesis

Example 54B Synthesis of methyl 2-bromo-4-nitrobenzoate: 2-bromo-4-nitrobenzoic acid (1.0 g, 4.06 mmol) and potassium carbonate (560 mg) were dissolved in N,N-dimethylformamide (5 mL), followed by the addition of iodomethane (500 μL, 8.03 mmol). The reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the mixture was poured into water (30 mL) and extracted with ether (3 x 10 mL). The combined ether layers were washed sequentially with water (1 × 10 mL) and brine (1 × 10 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to afford the target product methyl 2-bromo-4-nitrobenzoate (970 mg, 92% yield). The product was confirmed by 1H NMR (300 MHz, CDCl3): δ 8.52 (d, 1H, J=2.4 Hz), 8.21 (dd, 1H, J=2.0,8.5 Hz), 7.92 (d, 1H, J=8.8 Hz), 3.99 (s, 3H); the mass spectrum (ESI) showed m/z=259 (M-H).

References

[1] Patent: WO2013/148365, 2013, A1. Location in patent: Paragraph 00101
[2] Patent: US2002/35137, 2002, A1
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1702 - 1720

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