6-Bromovanillin Chemical Properties

Melting point:

178 °C

Boiling point:

326.2±37.0 °C(Predicted)

Density 

1.653±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform, DCM, Ethyl Acetate

form 

Solid

pka

6.83±0.23(Predicted)

color 

Brown

CAS DataBase Reference

60632-40-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

6-Bromovanillin Usage And Synthesis

Chemical Properties

White solid

Uses

6-Bromovanillin is used in the synthesis of Carbidopa (C175915), an inhibitor of aromatic amino acid decarboxylase.

Synthesis

The general procedure for the synthesis of 2-bromo-4-hydroxy-5-methoxybenzaldehyde from acetylvanillin is as follows: 1. 4-Formyl-2-methoxyphenyl acetate (5.00 g) and bromine (1.42 mL) were added to an aqueous solution (120 mL) of potassium bromide (10.3 g) and the mixture was stirred at room temperature for 8 hours. 2. The precipitate was collected by filtration and washed with water. 3. 6N hydrochloric acid (120 mL) was added to the resulting solid and the mixture was stirred at 90 °C for 16 hours. 4. The precipitate was collected by filtration and washed with saturated aqueous sodium bicarbonate and water. 5. The solid obtained was dissolved in ethyl acetate and the mixture was filtered through silica gel to give the title compound as a light yellow solid (yield: 4.88 g). 6. The resulting solid was recrystallized from ethyl acetate/n-heptane to give the title compound as a light yellow solid (yield: 3.98 g, 68%). 1H-NMR (DMSO-d6, 300 MHz): δ 3.83 (3H, s), 7.11 (1H, s), 7.34 (1H, s), 10.01 (1H, s), 10.86 (1H, br s).

References

[1] Journal of Organic Chemistry, 2002, vol. 67, # 18, p. 6493 - 6502
[2] Patent: EP2450352, 2012, A1. Location in patent: Page/Page column 80
[3] Journal of the American Chemical Society, 1927, vol. 49, p. 1079
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 17, p. 1967 - 1972
[5] Helvetica Chimica Acta, 1989, vol. 72, # 7, p. 1554 - 1582

6-Bromovanillin(60632-40-8)Related Product Information

• 3,7-Dimethyl-7-hydroxyoctanal
• o-Anisaldehyde
• 4-Hydroxybenzaldehyde
• Vanillin
• 2,6-Dimethoxybenzaldehyde
• Ethyl vanillin
• Salicylaldehyde
• Benzaldehyde
• CHLOROPHOSPHONAZO III
• p-Anisaldehyde
• 2-Bromo-5-methoxybenzaldehyde
• Veratraldehyde
• 3-Methoxysalicylaldehyde
• (Trifluoromethoxy)benzene
• 3-Methoxybenzaldehyde
• Bromine
• 6-Bromoveratraldehyde
• 2-BROMO-4,5-DIMETHOXYBENZOIC ACID