Synthesis of 2,4,6-tribromo-3,5-dimethylphenol

Preparation of 2,4,6-tribromo-3,5-dimethylphenol

A few g. of s-xylenol are placed in a large test tube or small beaker, and covered with about 20 times their weight of water. Bromine is gradually added drop by drop until an excess is indicated by a reddish-brown color which does not disappear. Sulfur dioxide, either as aqueous solution or gas, is added until the excess of bromine is removed.  The precipitate is filtered off, washed with water, and recrystallized from alcohol yielding 90% of 2,4,6-tribromo-3,5-dimethylphenol  as fine needles; m.p. 166 ° C.

Systematic organic chemistry, by W. M. Cumming, 353, 1937.

IUPAC Name

2,4,6-tribromo-3,5-dimethylphenol

InChI

InChI=1S/C8H7Br3O/c1-3-5(9)4(2)7(11)8(12)6(3)10/h12H,1-2H3

InChI Key

OXUOISZCFYHEAT-UHFFFAOYSA-N

Canonical SMILES

CC1=C(C(=C(C(=C1Br)O)Br)C)Br

Depositor-Supplied Synonyms

2,4,6-Tribromo-3,5-dimethylphenol, 56759-60-5, TRIBROMODIMETHYLPHENOL, Phenol, tribromodimethyl-, AC1L28BA, SCHEMBL6377646, OXUOISZCFYHEAT-UHFFFAOYSA-N, ZINC2001558, EINECS 260-366-4, 3,5-Dimethyl-2,4,6-tribromophenol, 2,4,6-tribromo-3,5-dimethyl-phenol, OR069976, OR286332, PHENOL,2,4,6-TRIBROMO-3,5-DIMETHYL-, 58170-32-4

Removed Synonyms

CID42665

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