2-CHLORO-3-HYDROXYBENZALDEHYDE 97 Chemical Properties

Melting point:

139-143 °C (lit.)

Boiling point:

245.0±20.0 °C(Predicted)

Density 

1.404±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

7.77±0.10(Predicted)

color 

Off-white to faint orange

InChIKey

SEEAPLJEIJXFFU-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-37/38-41-50

Safety Statements 

26-36-60-61

RIDADR 

UN 3077 9/PG 3

WGK Germany 

2

HazardClass 

9

PackingGroup 

Ⅲ

HS Code 

2913000090

2-CHLORO-3-HYDROXYBENZALDEHYDE 97 Usage And Synthesis

Uses

2-chloro-3-hydroxy-Benzaldehyde is a versatile building block used in the preparation of positional isomers of NOSH-aspirin a dual nitric oxide and hydrogen sulfide releasing hybrid pharmaceutical.

Synthesis

Under stirring conditions, tBuOCl (20 mL, 176 mmol) was slowly added dropwise to a suspension of 3-hydroxybenzaldehyde (20.12 g, 160 mmol) in HOAc (40 mL). The reaction solution gradually changed to a clarified solution with significant exothermic phenomenon. The reaction mixture was cooled and stirred continuously for 16 h, during which a white precipitate was generated. The solid product was collected by filtration, washed with deionized water and dried to afford 2-chloro-3-hydroxybenzaldehyde (13.77 g, 55% yield), which was analyzed by GCMS (EI) showing m/z 156,158 (M+). Subsequently, 2-chloro-3-hydroxybenzaldehyde (4.55 g, 29 mmol) was dissolved in DMF (30 mL), and K2CO3 (4.8 g, 34.9 mmol) and MeI (2.7 mL, 43.6 mmol) were added sequentially, and the reaction was stirred for 16 h at room temperature. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the residue was dissolved with ethyl acetate, washed with water and saturated saline in turn, dried over anhydrous Na2SO4 and concentrated. Purification was carried out by silica gel column chromatography with ethyl acetate/hexane (1:5) as eluent to obtain 2-chloro-3-methoxybenzaldehyde 3a (4.68 g, 94% yield) as a colorless oil, which was solidified after standing.GCMS (EI) analysis showed m/z 170,172 (M+).

References

[1] ACS Catalysis, 2018, vol. 8, # 5, p. 4033 - 4043
[2] Australian Journal of Chemistry, 2005, vol. 58, # 8, p. 565 - 571
[3] Patent: WO2005/7164, 2005, A1. Location in patent: Page 30-31
[4] Patent: WO2005/7165, 2005, A1. Location in patent: Page 46
[5] Patent: WO2005/7633, 2005, A1. Location in patent: Page 33

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