3,5-Dibromophenol Chemical Properties

Melting point:

79-83 °C (lit.)

Boiling point:

122°C/3mmHg(lit.)

Density 

1.8854 (rough estimate)

refractive index 

1.5380 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

pK1:8.056 (25°C)

color 

White to Light yellow to Light orange

Water Solubility 

Sightly soluble in water. Soluble in methanol.

InChIKey

PZFMWYNHJFZBPO-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29081990

MSDS

• Language:English Provider:3,5-Dibromophenol

3,5-Dibromophenol Usage And Synthesis

Chemical Properties

White to brown solid

Uses

3,5-Dibromophenol is used as a pharmaceutical intermediate. It is also used to prepare aromatic polyesters and drugs for arthritis.

Synthesis

General procedure for the synthesis of 3,5-dibromophenol from 3,5-dibromoanisole: 3,5-dibromoanisole (15.57 g, 58.5 mmol) and tetrabutylammonium bromide (1.0 g, 3.1 mmol) were suspended in 48% hydrobromic acid solution (100 mL), and heated to reflux for 3 days. After the reaction was completed, it was cooled to room temperature and the reaction mixture was extracted with dichloromethane (3 x 60 mL). The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/heptane, 10:1, v/v). After removal of the solvent, 14.23 g (97% yield) of 3,5-dibromophenol was obtained as light brown needle-like crystals.

References

[1] Journal of Organic Chemistry, 2004, vol. 69, # 25, p. 8982 - 8983
[2] Patent: US2006/270686, 2006, A1. Location in patent: Page/Page column 35
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 179 - 200
[4] Patent: US2008/280891, 2008, A1. Location in patent: Page/Page column 35
[5] Patent: WO2008/8059, 2008, A1. Location in patent: Page/Page column 96

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