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

Melting point:

125-127 °C (lit.)

Boiling point:

277.2±35.0 °C(Predicted)

Density 

1.6494 (rough estimate)

refractive index 

1.4730 (estimate)

storage temp. 

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

form 

solid

pka

7.62±0.23(Predicted)

Appearance

White to off-white Solid

Sensitive 

Air Sensitive

BRN 

2328601

CAS DataBase Reference

5034-74-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

29130000

MSDS

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

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

Chemical Properties

brown powder

Uses

5-Bromo-2-hydroxy-3-methoxybenzaldehyde may be employed for the following syntheses:

• ailanthoidol, via Stille coupling
• 6-bromo-8-methoxy-3-(methoxycarbonyl)-2H-chromen-2-one
• benzimidazole-based ligand, 2-(1H-benzoimidazol-2-yl)-4-bromo-6-methoxy-phenol (HL)
• chromogenic reagent, 5-bromo-2-hydroxy-3-methoxybenzaldehyde-p-hydroxy benzoic hydrazone
• (E)-N′-(5-bromo-2-hydroxy-3-methoxybenzylidene)-2-hydroxybenzohydrazide monohydrate

Synthesis

To a solution of o-vanillin (11; 4.0 g, 0.026 mol) in acetic acid (80 mL) was added sodium acetate (2.37 g, 0.029 mol) at 0 °C, followed by slow dropwise addition of bromine (1.49 mL, 0.029 mol). The reaction mixture was stirred at room temperature for 30 min. After completion of the reaction, water (100 mL) was added and the aqueous phase was extracted with dichloromethane (3 x 80 mL). The organic phases were combined, washed sequentially with water (100 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product was purified by fast column chromatography (petroleum ether:ethyl acetate = 19:1) to afford 5-bromo-2-hydroxy-3-methoxybenzaldehyde (26; 6.0 g, 98%) as a yellow solid with a melting point of 119-123 °C (literature value 19: 122-124 °C).1H NMR (400 MHz, CDCl3/TMS): δ = 3.92 (3H, s, OCH3), 7.18 (1H, d, J = 2.4 Hz, 4-H), 7.31 (1H, d, J = 2.4 Hz, 6-H), 9.86 (1H, s, CHO), 11.00 (1H, s, OH).13C NMR (100 MHz, CDCl3): δ = 56.3 (OCH3), 111.1 (C-5), 120.8 (C-6), 121.3 (C-1), 126.1 (C-4), 149.3 (C-2), 150.9 (C-3), 195.4 (CHO).The 1H NMR and 13C NMR data are in agreement with the literature values19.

References

[1] Synthesis (Germany), 2017, vol. 49, # 6, p. 1190 - 1205
[2] Journal of the Iranian Chemical Society, 2011, vol. 8, # 2, p. 531 - 536
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, p. 503 - 508
[4] Chemische Berichte, 1986, vol. 119, # 4, p. 1374 - 1399
[5] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 6, p. 1119 - 1123

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