4-Bromo-2,6-dimethylphenol Chemical Properties

Melting point:

74-78 °C (lit.)

Boiling point:

195.33°C (rough estimate)

Density 

1.3646 (rough estimate)

refractive index 

1.5650 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

10.10±0.23(Predicted)

color 

White to Light yellow to Light orange

Water Solubility 

Slightly soluble in water.

BRN 

1862399

InChI

InChI=1S/C8H9BrO/c1-5-3-7(9)4-6(2)8(5)10/h3-4,10H,1-2H3

InChIKey

ZLVFYUORUHNMBO-UHFFFAOYSA-N

SMILES

C1(O)=C(C)C=C(Br)C=C1C

CAS DataBase Reference

2374-05-2(CAS DataBase Reference)

NIST Chemistry Reference

Phenol, 4-bromo-2,6-dimethyl-(2374-05-2)

EPA Substance Registry System

Phenol, 4-bromo-2,6-dimethyl- (2374-05-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

ZE6780000

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29081990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Bromo-2,6-dimethylphenol Usage And Synthesis

Chemical Properties

LIGHT PINK-BEIGE TO BROWN CRYSTALS OR POWDER

Uses

It is used as a preservatives for coatings, slurries and to control microbial fouling in paper mills , oil field and leather process and water treatment process against microbial attack.

Preparation

4-Bromo-2,6-dimethylphenol is prepared by bromination of 2,6-dimethylphenol in glacial acetic acid at 15 ℃ and used as a microbicide in disinfectants.

General Description

Iodine initiated polymerization of 4-bromo-2,6-xylenol in tetrahydrofuran solution has been investigated. 4-Bromo-2,6-xylenol on bromination in chloroform or carbobn tetrachloride yields 3,4-dibromo-2,6-xylenol and 3,4,5-tribromo-2,6-xylenol.

Synthesis

In a 10 mL two-neck flask equipped with a reflux condenser, 2,6-dimethylphenol (0.25 mmol) and tetrabutylammonium bromide (161.2 mg, 0.50 mmol) were added. The flask was evacuated and backfilled three times with argon. To the reaction mixture was added ultrapure water (0.5 mL), trifluoroacetic acid (57.5 μL, 0.75 mmol) and 30% hydrogen peroxide (77 μL, 0.75 mmol). The reaction mixture was stirred at 25 °C under argon protection. Upon completion of the reaction, the reaction was quenched with 1:1 saturated aqueous sodium thiosulfate and saturated aqueous sodium bicarbonate and extracted with ether. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. 1,3,5-Trimethoxybenzene or hexamethylbenzene was added as an internal standard and the NMR yield of the product was determined by 1H NMR analysis. The spectral data obtained for 4-bromo-2,6-dimethylphenol were consistent with those of commercially available standards.

Toxicity evaluation

LD50 (i.p., mouse) 650 mg/kg.

References

[1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 10, p. 3373 - 3375
[2] Synthetic Communications, 2010, vol. 40, # 21, p. 3226 - 3232
[3] Organic Letters, 2006, vol. 8, # 19, p. 4291 - 4293
[4] Chinese Chemical Letters, 2012, vol. 23, # 4, p. 387 - 390
[5] Organic Letters, 2015, vol. 17, # 12, p. 2886 - 2889

4-Bromo-2,6-dimethylphenol(2374-05-2)Related Product Information

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