2,4,6-Tribromophenol

• Bromol
• TBP

Whitish- pink scales

Fixed

2.55 g · cm -3 ( 20 ° C)

87-90 ° C

282-290 ° C

7 mPa

6.08

Very poor in water ( 71 mg · l-1 at 15 ° C)

Attention

2000 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

2,4,6-tribromophenol (TBP ) is a chemical compound that includes both of the phenols and the haloaromatic compound. The structure consists of a benzene ring with an added hydroxy (-OH) and three bromine atoms ( Br ) as a substituent. It is, inter alia, used as a flame retardant.

Representation

2,4,6 -tribromophenol caused by direct bromination of phenol with elemental bromine in the presence of potassium bromide. Continued, while bromine is used in excess, it reacts to form 2,4,6-tribromophenol 2,4,4,6 -tetrabromo -2 ,5 -cyclohexadienone ( Tribromphenolbrom, melting point 124 ° C, age- trivial name ). This secondary reaction can be reversed with hydrogen iodide.

Properties

2,4,6 -tribromophenol forms whitish- pink scales, which melt at 87-90 ° C. The boiling point is 282-290 ° C. Due to the effect of I - bromo, it has a higher acidity in comparison with the phenol. The pK a value of 6.08 is therefore significantly lower ( phenol: 9.99).

Reactions

In the nitration of 2,4,6-tribromophenol the bromine atom at the para - position is replaced by the nitro group, it is 2,6- dibromo- 4-nitrophenol. Assuming however the ethyl ether of 2,4,6- tribromophenol, the nitro group is attached at the 3 position, so it forms 1-ethoxy -2 ,4,6- tribromo -3 -nitrobenzene. Organisms metabolize 2,4,6 -tribromophenol to 2,4,6- tribromoanisole.

By boiling with zinc dust and glacial acetic acid from the bromine atom ortho position is eliminated, there is produced 2,4- dibromophenol.