4-Bromo-2,5-dimethylphenol Chemical Properties

Melting point:

87 °C

Boiling point:

259.0±35.0 °C(Predicted)

Density 

1.471±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

solid

pka

9.87±0.23(Predicted)

color 

white

Safety Information

HS Code 

2908190090

4-Bromo-2,5-dimethylphenol Usage And Synthesis

Uses

4-Bromo-2,5-dimethylphenol is a phenol derivative whose benzene ring structure is substituted with methyl and bromine atoms on 2, 5 and 4. This product can be used as an organic synthesis intermediate for the preparation of other polymeric organics.

Synthesis

A solution of tetrabutylammonium tribromide (19.9 g, 41.39 mmol) in chloroform (150 mL) was slowly added dropwise to a stirred suspension of 2,5-dimethylphenol (5.0 g, 40.9 mmol) in water (150 mL) at room temperature. The reaction mixture was stirred continuously for 2 hours at room temperature. Upon completion of the reaction, the organic layer was separated and dried with anhydrous sodium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by silica gel column chromatography with the eluent being a hexane-ethyl acetate solvent mixture of 1:5, v/v, to give 2,5-dimethyl-4-bromophenol as a brown solid (6.2 g, 76% yield). The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6): δ 9.47 (s, 1H), 7.24 (s, 1H), 6.74 (s, 1H), 2.21 (s, 3H), 2.07 (s, 3H). Thin-layer chromatography (TLC) analysis conditions: Uniplate silica gel plates, 250 µm thickness; mobile phase was hexane-ethyl acetate in 9:1 volume ratio; Rf value was 0.52.

References

[1] Tetrahedron, 2007, vol. 63, # 34, p. 8242 - 8249
[2] Letters in Organic Chemistry, 2018, vol. 15, # 8, p. 682 - 687
[3] Journal of the Chilean Chemical Society, 2011, vol. 56, # 4, p. 863 - 865
[4] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 11, p. 4187 - 4189
[5] Synthetic Communications, 2010, vol. 40, # 6, p. 868 - 876

4-Bromo-2,5-dimethylphenol(85223-93-4)Related Product Information

• 3-Bromophenol
• 3-Bromoanisole
• 3,5-Dimethylphenol
• Xylenol
• 2,4-Dichlorophenol
• 2,5-Dimethylphenol
• 4-Bromophenol
• PHENOLDISULFONIC ACID
• Dimethyl sulfoxide
• N,N-Dimethylformamide
• Bromine
• 2,4-DIBROMO-3-ISOPROPYL-6-METHYLBENZENOL
• 1-BROM0-4-METHOXY-2 5-DIMETHYLBENZENE&
• 5-BROMO-2-HYDROXY-4-METHYL-BENZALDEHYDE
• 4-BROMO-1-HYDROXYANTHRAQUINONE-2-CARBOXYLIC ACID
• 4-BROMO-2,3,6-TRIMETHYL-PHENOL
• 4-Bromo-2,5-dimethylphenol
• 4-BROMO-5-ISOPROPYL-2-METHYLPHENYL 4-METHOXYBENZENECARBOXYLATE