PHENOL, 5-BROMO-2-NITRO- Chemical Properties

Melting point:

40-420C

Boiling point:

264.6±20.0 °C(Predicted)

Density 

1.881±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in ethyl acetate and methanol.

pka

6.08±0.13(Predicted)

form 

Crystalline Solid

color 

Pale yellow

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37-60

RIDADR 

2811

HS Code 

29089990

PHENOL, 5-BROMO-2-NITRO- Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

It is used as pharmaceutical intermediate.

Synthesis

Potassium nitrate (51.5 g, 509 mmol) was slowly added to a mixed solution of concentrated sulfuric acid (32.6 mL) and water (105 mL) at 10 °C. The reaction mixture was stirred for 5 min and then 3-bromophenol (49.35 g, 285 mmol) was added dropwise while the reaction temperature was controlled to be maintained at about 10 °C. After addition, the reaction mixture was continued to be stirred at room temperature for 2 hours. Upon completion of the reaction, the reaction solution was diluted with water (350 mL) and subsequently extracted with ether. The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by fast column chromatography (silica gel, 19:1 hexane/ethyl acetate) to afford 5-bromo-2-nitrophenol (11.3 g, 18% yield) as a yellow-green solid. Its 1H NMR (DMSO-d6, 300 MHz) data were as follows: δ 11.44 (s, 1H), 7.84 (d, J = 8.7 Hz, 1H), 7.33 (d, J = 2.1 Hz, 1H), 7.18 (dd, J = 8.7, 2.1 Hz, 1H).

References

[1] Chemistry - A European Journal, 2011, vol. 17, # 33, p. 9076 - 9082
[2] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 108 - 119
[3] Journal of Organic Chemistry, 1990, vol. 55, # 9, p. 2736 - 2742
[4] Patent: WO2011/44134, 2011, A1. Location in patent: Page/Page column 107
[5] Patent: EP1956013, 2008, A1. Location in patent: Page/Page column 37

PHENOL, 5-BROMO-2-NITRO-(27684-84-0)Related Product Information

• 2-NITRO 5-BROMO-BENZALDEHYDE
• 5-METHYL-2-NITROANILINE
• 2-nitro-6-chloroaniline
• 4,5-DICHLORO-2-NITROTOLUENE
• Benzene, 1-chloro-2-fluoro-4-methyl-5-nitro-
• 3-BROMO-5-HYDROXY-2,6-DINITRO-BENZOIC ACID
• 1-bromo-2,5-dimethoxy-4-nitrobenzene
• 4-bromo-2-methoxy-1-nitrobenzene
• 3-BROMO-5-METHOXY-2,6-DINITRO-BENZOIC ACID METHYL ESTER
• PHENOL, 5-BROMO-2-NITRO-
• 3-BROMO-5-BENZYLOXY-2,6-DINITROBENZOIC ACID BENZYL ESTER