2-BROMO-3-HYDROXY-4-METHOXYBENZALDEHYDE Chemical Properties

Melting point:

202-207 °C (lit.)

Boiling point:

289.5±35.0 °C(Predicted)

Density 

1.653±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Dichloromethane, Ethyl Acetate

form 

Solid

pka

7.71±0.15(Predicted)

color 

Off-White

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

2-BROMO-3-HYDROXY-4-METHOXYBENZALDEHYDE Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

Taspine intermediate.

Uses

2-Bromo-3-hydroxy-4-methoxybenzaldehyde (2-Bromo-isovanillin) may be used in the preparation of:

• 2-hydroxy-3-methoxybenzaldehyde semicarbazone (HMBS)
• 2-cyclopentyl-7-methoxy-1-benzofuran-4-carbaldehyde
• 3-(benzyloxy)-2-bromo-4-methoxybenzaldehyde

It may also be used as a starting material in the total synthesis of the following natural products:

• pareitropone
• denbinobin
• (±)-codeine

General Description

2-Bromo-3-hydroxy-4-methoxybenzaldehyde, also known as 2-bromo-isovanillin, can be synthesized by the bromination of 3-hydroxy-4-methoxybenzaldehyde.

Synthesis

General procedure for the synthesis of 2-bromo-3-hydroxy-4-methoxybenzaldehyde from isovanillin: 3-hydroxy-4-methoxybenzaldehyde (10.0 g, 65.7 mmol) was dissolved in dichloromethane (150 mL), followed by addition of N-bromosuccinimide (NBS, 11.7 g, 65.7 mmol) at room temperature. The reaction mixture was stirred for 30 min at room temperature. Upon completion of the reaction, the target product 2-bromo-3-hydroxy-4-methoxybenzaldehyde (14.1 g, 93% yield) was obtained by conventional post-treatment.

References

[1] Synthesis (Germany), 2018, vol. 50, # 5, p. 1053 - 1089
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 42, p. 7851 - 7860
[3] Organic and Biomolecular Chemistry, 2007, vol. 5, # 9, p. 1466 - 1471
[4] Angewandte Chemie - International Edition, 2011, vol. 50, # 17, p. 3892 - 3894
[5] Synlett, 2000, # 8, p. 1163 - 1165

2-BROMO-3-HYDROXY-4-METHOXYBENZALDEHYDE(2973-58-2)Related Product Information

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