1-BROMO-2,6-DIMETHOXYBENZENE Chemical Properties

Melting point:

91-94°C

Boiling point:

250℃

Density 

1.412

Flash point:

106℃

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

color 

White to Orange to Green

Water Solubility 

Insoluble in water.

InChI

InChI=1S/C8H9BrO2/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5H,1-2H3

InChIKey

VHVYSMMZHORFKU-UHFFFAOYSA-N

SMILES

C1(OC)=CC=CC(OC)=C1Br

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2909.30.6000

1-BROMO-2,6-DIMETHOXYBENZENE Usage And Synthesis

Chemical Properties

off-white crystalline solid

Uses

2-Bromo-1,3-dimethoxybenzene is used as a pharmaceutical intermediate.

Synthesis

The general procedure for the synthesis of 2,6-dimethoxybromobenzene from m-anisidine is as follows: Example Preparation Example (A) Synthesis of intermediate (A) (A-1) Synthesis of 1-bromo-2,6-dimethoxybenzene Under argon protection, 19.3 g of 1,3-dimethoxybenzene and 500 mL of anhydrous ether were added to a flask. 105 mL (1.6 M) of hexane solution of n-butyllithium was slowly added and the reaction mixture was heated and stirred for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature, followed by further cooling to -50°C. At this temperature, 25 g of bromine was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was gradually warmed to room temperature and stirring was continued for 2 hours. At the end of the reaction, 300 mL of 10% aqueous sodium thiosulfate solution was added and stirred for 1 hour to quench the reaction. The reaction mixture was extracted with ether, and the organic phase was separated and washed with saturated brine. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. The resulting crystals were washed with hexane to give 17.9 g (yield: 52%) of white crystals of 1-bromo-2,6-dimethoxybenzene.

References

[1] Journal of the Chemical Society, Chemical Communications, 1995, # 6, p. 611 - 612
[2] Journal of Organic Chemistry, 2006, vol. 71, # 2, p. 775 - 788
[3] Patent: EP2436679, 2012, A1. Location in patent: Page/Page column 46
[4] Patent: JP2015/7036, 2015, A. Location in patent: Paragraph 0234; 0236
[5] Helvetica Chimica Acta, 1990, vol. 73, # 1, p. 48 - 62

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