3-CHLORO-5-HYDROXYBENZALDEHYDE Chemical Properties

Melting point:

104 °C

Boiling point:

268.3±20.0 °C(Predicted)

Density 

1.404±0.06 g/cm3(Predicted)

storage temp. 

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

pka

8.28±0.10(Predicted)

Appearance

Light brown to brown Solid

Safety Information

HS Code 

2912490090

3-CHLORO-5-HYDROXYBENZALDEHYDE Usage And Synthesis

Synthesis

Using 3-chloro-5-methoxybenzaldehyde (22.8 g, 134 mmol) as starting material, it was dissolved in dichloromethane (250 mL) and the solution was cooled to 0°C. Boron tribromide (15.8 mL, 167 mmol) was slowly added dropwise over a period of 15 min. After the dropwise addition was completed, the reaction mixture continued to be stirred at 0°C for 2 hr. Subsequently, water (50 mL) was added slowly to quench the reaction. The reaction mixture was extracted with ether (2 x 100 mL), the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. Purification by silica gel column chromatography using hexane: ethyl acetate (4:1) as eluent gave the target product 3-chloro-5-hydroxybenzaldehyde (5.2 g, 25% yield). The product was confirmed by 1H NMR (300 MHz, CDCl3): δ 9.85 (s, 1H), 7.35 (s, 1H), 7.20 (s, 1H), 7.10 (s, 1H), 3.68 (s, 1H).

References

[1] Patent: WO2003/101957, 2003, A1. Location in patent: Page 29-30
[2] Patent: US2004/19033, 2004, A1. Location in patent: Page/Page column 16
[3] Patent: WO2003/101423, 2003, A1. Location in patent: Page 19-20
[4] Patent: WO2003/101424, 2003, A1. Location in patent: Page 21-22
[5] Patent: WO2003/101956, 2003, A1. Location in patent: Page 40

3-CHLORO-5-HYDROXYBENZALDEHYDE(1829-33-0)Related Product Information

• 5-CHLOROVANILLIC ACID
• 2,5-Dichloro-3-hydroxy-6-methoxybenzoic acid
• 3-CHLORO-5-ETHOXY-4-HYDROXYBENZALDEHYDE
• 1-AMINO-2-CHLORO-4-HYDROXY-9,10-ANTHRACENEDIONE
• 3-CHLORO-5-METHOXY-BENZOIC ACID
• 5-CHLOROVANILLIN
• 3-CHLORO-4,5-DIETHOXYBENZALDEHYDE
• 3-CHLORO-4-ETHOXY-5-METHOXYBENZALDEHYDE
• AKOS B004773
• 4-(BENZYLOXY)-3-CHLORO-5-METHOXYBENZALDEHYDE
• 7-CHLORO-1,3-BENZODIOXOLE-5-CARBALDEHYDE
• 5-CHLORO-2-HYDROXY-3-METHOXYBENZALDEHYDE
• 5,6-DICHLORO-4-HYDROXY-3-METHOXYBENZOIC ACID
• ETHYL 2-(4-CHLORO-2-FORMYL-6-METHOXYPHENOXY)ACETATE
• RARECHEM AL BI 0696
• 2-CHLOROQUINIZARIN
• RARECHEM AL BE 0860