2,5-DIBROMOPHENOL Chemical Properties

Melting point:

73-74 °C

Boiling point:

244.6±20.0 °C(Predicted)

Density 

2.095±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

powder

pka

7.47±0.10(Predicted)

color 

White

InChI

InChI=1S/C6H4Br2O/c7-4-1-2-5(8)6(9)3-4/h1-3,9H

InChIKey

GUXWVUVLXIJHQF-UHFFFAOYSA-N

SMILES

C1(O)=CC(Br)=CC=C1Br

Safety Information

HS Code 

2908190090

2,5-DIBROMOPHENOL Usage And Synthesis

Chemical Properties

2,5-Dibromophenol is a white to pale yellow powder, slightly soluble in water, very slightly soluble in chloroform and methanol. It should be stored under an inert atmosphere and at room temperature to maintain its stability.

Uses

2,5-Dibromophenol is an important intermediate in organic synthesis and is often used to synthesize other complex organic molecules.

Synthesis

General procedure for the synthesis of 2,5-dibromophenol from 2,5-dibromoaniline: Sodium nitrite (65.2 mmol) was added in batches to a solution of trifluoroacetic acid (80 mL) containing 2,5-dibromoaniline (55.8 mmol) at 0 °C. Subsequently, the resulting solution was slowly added to a boiling solution of 50% sulfuric acid (120 mL) containing sodium sulfate (10 g) and the reaction mixture was kept at reflux for 1 hour. Upon completion of the reaction, the product was steam distilled and the distillate was extracted using dichloromethane (2 x 200 mL). The organic layers were combined, dried over sodium sulfate and concentrated to give 2,5-dibromophenol as a yellow solid in 41% yield.

References

[1] Environmental Science and Technology, 2001, vol. 35, # 18, p. 3749 - 3756
[2] Patent: WO2009/23844, 2009, A2. Location in patent: Page/Page column 129-130
[3] Patent: US2010/16297, 2010, A1. Location in patent: Page/Page column 33-34
[4] Patent: WO2010/21797, 2010, A1. Location in patent: Page/Page column 94-95
[5] Patent: US2010/29629, 2010, A1. Location in patent: Page/Page column 62

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