5-BROMOSALICYLAMIDE Chemical Properties

Melting point:

241-245 °C(lit.)

Boiling point:

316.6±32.0 °C(Predicted)

Density 

1.759±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

7.79±0.18(Predicted)

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-43

Safety Statements 

28-36/37

WGK Germany 

3

RTECS 

VN7000000

MSDS

• Language:English Provider:SigmaAldrich

5-BROMOSALICYLAMIDE Usage And Synthesis

Application

5-Bromosalicylate is an amide organic compound that can be used as a pharmaceutical synthesis intermediate.

Synthesis

A. Procedure for the synthesis of 5-bromo-2-hydroxybenzamide: 1. In a 100 mL round-bottom flask, 5-bromosalicylic acid (30 g, 135.5 mmol) was dissolved in n-butanol (60 mL) and concentrated sulfuric acid (95.6%, 289 μL, 5.42 mmol) was added. The unit was equipped with a Dean-Stark manifold and reflux condenser and 12 mL of n-butanol was added. 2. Reflow the reaction mixture under heat for 2 days. Upon completion of the reaction, it was cooled to room temperature and concentrated to give a light yellow oil. 3. Methanol (50 mL) was added to the above oil, followed by the slow addition of a methanol solution of ammonia (7 N, 116 mL). 4. The reaction mixture was stirred at room temperature for 2 days and the progress of the reaction was monitored by HPLC. 5. 5. After completion of the reaction, the reaction mixture was concentrated to give a white solid. 6. The crude product was washed with a small amount of ethyl acetate and hexane to give 24 g of white crystalline solid in 82% yield.

References

[1] Patent: WO2005/95326, 2005, A2. Location in patent: Page/Page column 253
[2] Patent: US2018/64726, 2018, A1. Location in patent: Paragraph 0360; 0361
[3] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 4, p. 734 - 745
[4] Patent: US2006/14737, 2006, A1. Location in patent: Page/Page column 25

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