3-CHLORO-5-HYDROXYBENZALDEHYDE

3-CHLORO-5-HYDROXYBENZALDEHYDE Property

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

HS Code 

2912490090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

3-CHLORO-5-HYDROXYBENZALDEHYDE Chemical Properties,Usage,Production

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