3-Bromoanisole

Chemical properties

3-Bromoanisole, also known as m-Bromoanisole, is a clear colorless to pale yellow oily liquid. The boiling point is 210-211°C (100kPa), 105°C (2.13kPa), the relative density is 1.477, the refractive index is 1.5635, and the flash point is 93°C. It is soluble in alcohol, ether, benzene, and carbon disulfide, but insoluble in water. It is commonly used as a raw material for organic synthesis.

The Uses of 3-Bromoanisole

3-Bromoanisole used in chemical reaction as intermediates to obtain target materials such as dyes, pharmaceuticals, perfumes, photoinitiators and agrochemicals.

Preparation

3-Bromoanisole is synthesized through a reaction between m-bromophenol and dimethyl sulfate. The synthesis method involves the following steps:
Dissolve m-bromophenol in a sodium hydroxide solution.
Slowly add dimethyl sulfate dropwise to the solution while stirring.
Heat the mixture and allow it to react for 1 hour.
Cool the reaction mixture to separate the colorless oil formed.
Extract the water layer with ether.
Dry the ether extract and then distill it to recover the ether.
Distill the residue obtained after recovering the ether, along with the colorless oil, under reduced pressure.
This distillation process results in the production of m-bromoanisole as the final product.
The overall yield of m-bromoanisole achieved through this process is 90%.

References

Application of Anisole, 2-Bromoanisole and 3-Bromoanisole as Overcharge Protection Additives in Lithium-Ion Batteries DOI:10.6023/A12110964
S. Ramalingam; S. Periandy. Spectroscopic investigation, computed IR intensity, Raman activity and vibrational frequency analysis on 3-bromoanisole using HF and DFT (LSDA/MPW1PW91) calculations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2011, 78 (2), 835-843. DOI:10.1016/j.saa.2010.12.043
Bobby Glover; Kimberly A. Harvey; Bing Liu; Matthew J. Sharp; and Maria F. Tymoschenko. Regioselective Palladium-Catalyzed Arylation of 3-Carboalkoxy Furan and Thiophene. Org. Lett. 2003, 5 (3), 301-304. DOI:10.1021/ol027266q