2-Bromo-3-nitroanisole Chemical Properties

Boiling point:

273.3±20.0 °C(Predicted)

Density 

1.640±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder

color 

Yellow

InChI

InChI=1S/C7H6BrNO3/c1-12-6-4-2-3-5(7(6)8)9(10)11/h2-4H,1H3

InChIKey

KCFDURKFXBLIAY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

67853-37-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-22

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2909309090

2-Bromo-3-nitroanisole Usage And Synthesis

Uses

2-Bromo-3-nitroanisole belongs to the class of bromoanisoles and can be used to synthesize rhodopsin coupling promoters and new drugs.

Synthesis

General procedure for the synthesis of 2-bromo-3-nitroanisole from 2-bromo-3-nitrophenol (3.1 g, 14.2 mmol) and iodomethane (2.6 mL, 42.5 mmol): 2-bromo-3-nitrophenol was dissolved in N,N-dimethylformamide (DMF, 20 mL), to which was added ground cesium carbonate (5.58 g, 17.1 mmol), followed by the addition of iodomethane. The reaction mixture was stirred at room temperature overnight. After completion of the reaction, DMF was removed by rotary evaporator and the residue was dissolved in ether (200 mL) and washed sequentially with water (200 mL) and saturated sodium chloride solution (4 x 100 mL). The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated to give the crude product 2-bromo-3-nitroanisole (94% yield, 3.1 g) as an orange solid. Mass spectrometry (MS) analysis showed m/z 234 ([M+2H]+). High performance liquid chromatography (HPLC, TFA system, 220 nm detection) showed a product purity of 98%.

References

[1] Patent: WO2004/103996, 2004, A1. Location in patent: Page 40-41
[2] Patent: WO2006/7700, 2006, A1. Location in patent: Page/Page column 62
[3] Patent: US2006/19905, 2006, A1. Location in patent: Page/Page column 24
[4] Patent: WO2006/85, 2006, A1. Location in patent: Page/Page column 75-76
[5] Patent: WO2007/9227, 2007, A1. Location in patent: Page/Page column 35

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