2-CHLORO-6-HYDROXYBENZALDEHYDE Chemical Properties

Melting point:

51-55℃

Boiling point:

223.1±20.0 °C(Predicted)

Density 

1.404±0.06 g/cm3(Predicted)

Flash point:

107℃

storage temp. 

2-8°C

pka

7.21±0.10(Predicted)

form 

powder to crystal

color 

White to Light yellow to Light orange

InChI

InChI=1S/C7H5ClO2/c8-6-2-1-3-7(10)5(6)4-9/h1-4,10H

InChIKey

MVTWVXYIKIVAOJ-UHFFFAOYSA-N

SMILES

C(=O)C1=C(O)C=CC=C1Cl

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26-39

WGK Germany 

3

HS Code 

2912490090

2-CHLORO-6-HYDROXYBENZALDEHYDE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 6-chlorosalicylaldehyde from 2-chloro-6-fluoro-benzaldehyde was as follows: potassium hydroxide (10 g) was slowly added to a stirred solution of 2-chloro-6-fluoro-benzaldehyde (14.0 g, 88.3 mmol) in dimethyl sulfoxide (20 mL) at 0 °C. Subsequently, the reaction mixture was gradually warmed to room temperature and stirred continuously for 18 hours. Upon completion of the reaction, the reaction mixture was diluted with 100 mL of water and the pH was adjusted with concentrated hydrochloric acid to 2. The precipitate was collected by filtration, washed twice successively with 100 mL of water, and then dried with anhydrous sodium sulfate to afford the crude product, which was used in the subsequent reaction without further purification. The final yield was 8.5 g in 62% yield. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3) with δppm 6.65-7.02 (m, 2H), 7.39-7.47 (m, 1H), 10.41 (s, 1H), 11.95 (s, 1H).

References

[1] European Journal of Organic Chemistry, 2018, vol. 2018, # 25, p. 3348 - 3351
[2] Patent: WO2012/87229, 2012, A1. Location in patent: Page/Page column 14
[3] Patent: US2008/171754, 2008, A1. Location in patent: Page/Page column 89
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 12, p. 1345 - 1358
[5] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie, 1972, vol. 27, p. 663 - 674

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