4-Bromo-2,5-dimethoxybenzaldehyde Chemical Properties

Melting point:

132-135°C

Boiling point:

337.1±42.0 °C(Predicted)

Density 

1.482±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

solid

color 

Faint yellow to yellow

Water Solubility 

Insoluble in water.

Stability:

Hygroscopic

InChI

InChI=1S/C9H9BrO3/c1-12-8-4-7(10)9(13-2)3-6(8)5-11/h3-5H,1-2H3

InChIKey

BIFWGDWGCZLCHF-UHFFFAOYSA-N

SMILES

C(=O)C1=CC(OC)=C(Br)C=C1OC

Safety Information

HS Code 

2913000090

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

Uses

4-Bromo-2,5-dimethoxybenzene is used as a pharmaceutical intermediate.

Synthesis

At 0 °C, 2,5-dimethoxybenzaldehyde (1.0 g, 6.02 mmol) was dissolved in glacial acetic acid (7 mL) and a solution of bromine (0.34 mL, 6.62 mmol) in glacial acetic acid (3 mL) was slowly added. The reaction mixture was gradually warmed to room temperature and stirred continuously for 1 hour. Upon completion of the reaction, water (30 mL) was added to quench the reaction and the resulting white precipitate was collected by filtration. The precipitate was redissolved in water (30 mL) and dichloromethane (30 mL) for liquid-liquid separation. The aqueous phase was extracted with dichloromethane (3 x 25 mL), and all organic phases were combined, washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluent: 20% ethyl acetate/hexane) to afford 4-bromo-2,5-dimethoxybenzaldehyde as a light yellow solid (0.83 g, 3.37 mmol, 56% yield).

References

[1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 35, p. 5782 - 5786
[2] Tetrahedron, 2011, vol. 67, # 21, p. 3904 - 3914
[3] Journal of the American Chemical Society, 2011, vol. 133, # 40, p. 15870 - 15873
[4] Synthetic Communications, 1998, vol. 28, # 24, p. 4629 - 4637
[5] Tetrahedron Letters, 2003, vol. 44, # 16, p. 3281 - 3284

4-Bromo-2,5-dimethoxybenzaldehyde (31558-41-5)Related Product Information

• 4-Bromo-2,5-dimethylbenzoic acid
• 4-Bromo-2,5-dimethylphenylboronic acid
• 4-BROMO-2,5-DIMETHOXY-PHENOL
• (4-BROMO-2,5-DIMETHOXYPHENYL)METHANOL
• 4-BROMO-2,5-DIMETHOXYBENZOIC ACID
• 4-Bromo-2-hydroxybenzaldehyde
• 2-Bromo-4-methoxybenzenol
• 5-Bromo-2-methylphenol
• 4-Bromo-2,5-dimethoxybenzaldehyde
• BROMOHYDROQUINONE
• 4-BROMO-2-METHOXYBENZALDEHYDE
• 1-Bromo-2,5-dimethoxybenzene
• 4-BROMO-2,5-DIMETHOXYTOLUENE
• 2,5-Dimethoxybenzaldehyde
• 4-BROMO-3-HYDROXYBENZALDEHYDE
• 2-BROMO-4-METHOXYPHENOL
• 4-BROMO-3-METHOXYPHENYL-P-TOLUENESULFONATE
• 4-BROMO-2-METHOXYTOLUENE