4-BROMO-2-METHYL-1-NITROBENZENE Chemical Properties

Melting point:

53-55℃

Boiling point:

265℃

Density 

1.615

refractive index 

1.6120 (estimate)

Flash point:

114℃

storage temp. 

Sealed in dry,Room Temperature

Appearance

White to light yellow Solid

Safety Information

HS Code 

2929900090

4-BROMO-2-METHYL-1-NITROBENZENE Usage And Synthesis

Uses

5-Bromo-2-nitrotoluene is used the synthesis of biphenylamide derivatives as Hsp90 C-terminal inhibitor for the treatment of cancer and neurodegenerative diseases.

Synthesis

General procedure for the synthesis of 4-bromo-2-methyl-1-nitrobenzene from 2-methyl-4-bromoaniline: Step 1: Synthesis of 4-bromo-2-methyl-1-nitrobenzene (193) H2O2 (3.95 mL, 64±5 mmol) was dissolved in DCM (320 mL) at 0°C, cooled and TFAA (10.93 mL, 77 mmol) was added and the mixture was stirred for 5 min at this temperature. The ice bath was then removed, a reflux condenser was installed, and a solution of 4-bromo-2-methylaniline (3 g, 16.12 mmol) in DCM (6.4 mL) was added slowly and dropwise over about 30 minutes. The reaction mixture was heated to reflux for 1 h. After cooling, the reaction mixture was washed sequentially with 30 mL of water and 30 mL of saturated NaHCO3 solution, and the organic layer was dried with MgSO4 and concentrated in vacuum. The crude product was purified by flash column chromatography to give 193 (2.57 g, 11.9 mmol, 74% yield). 1H NMR (CDCl3) δ (ppm): 7.88 (d, J = 8.6 Hz, 1H), 7.53 (d, J = 2.2 Hz, 1H), 7.49 (dd, J = 8.6, 2.2 Hz, 1H), 2.60 (s, 3H).

References

[1] Patent: WO2008/104077, 2008, A1. Location in patent: Page/Page column 122
[2] Journal of Organic Chemistry, 1955, vol. 20, p. 1458
[3] Patent: US4287201, 1981, A

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