Chemical Properties
Low melting solid
Uses
4-Bromo-3-nitrotoluene may be used as a starting material in the synthesis of 2-bromo-5-methylaniline and as a reagent in the synthesis of 2-nitro-4:4′-dimethyl-diphenyl by reacting with
p-iodotoluene.
General Description
4-Bromo-3-nitrotoluene (2-bromo-5-methylnitrobenzene, 1-bromo-4-methyl-2-nitrobenzene) is a halonitrobenzene. It has been synthesized from 4-methyl-2-nitroaniline and confirmed by
1H NMR. The crystal structure of 1-bromo-4-methyl-2-nitrobenzene is found to be orthorhombic in the
Pna2
1 space group. Its enthalpy of vaporization at boiling point has been determined.
Synthesis
To a Silak reaction tube equipped with a magnetic stirrer were sequentially added 6.2 mg of silver sulfate, 36.3 mg of copper acetate, 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline, 36.2 mg of 4-methyl-2-nitrobenzoic acid, and 30.9 mg of sodium bromide, followed by the addition of 4 mL of dimethyl sulfoxide as a solvent. The reaction mixture was heated and stirred at 160 °C for 24 hours under an oxygen atmosphere. Upon completion of the reaction, the reaction was quenched by addition of appropriate amount of distilled water and extracted three times with ethyl acetate (10 mL each time). The organic phases were combined and concentrated to give 29.8 mg of 4-bromo-3-nitrotoluene in 69% yield.
References
[1] Patent: CN107325002, 2017, A. Location in patent: Paragraph 0091
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
[3] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2794 - 2803
