2,3-Dihydroxybenzaldehyde Chemical Properties

Melting point:

104-108 °C (lit.)

Boiling point:

120 °C / 16mmHg

Density 

1,542g/cm

refractive index 

1.4600 (estimate)

storage temp. 

Inert atmosphere,2-8°C

solubility 

95% ethanol: soluble50mg/mL, clear, colorless to greenish-yellow

form 

Crystalline Powder

pka

8.01±0.10(Predicted)

color 

Light yellow to beige-greenish

Sensitive 

Air Sensitive

BRN 

2041781

InChIKey

IXWOUPGDGMCKGT-UHFFFAOYSA-N

LogP

1.325 (est)

CAS DataBase Reference

24677-78-9(CAS DataBase Reference)

NIST Chemistry Reference

2,3-Dihydroxybenzaldehyde(24677-78-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

10-23

HS Code 

29124900

MSDS

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2,3-Dihydroxybenzaldehyde Usage And Synthesis

Chemical Properties

light yellow to beige-greenish cryst. powder

Uses

2,3-disubstituted benzaldehyde.

Uses

2,3-Dihydroxybenzaldehyde was used in the synthesis of copper(II) complexes of Schiff bases. It was also used in the synthesis of 2-ethoxy-3-hydroxy-4-nitrobenzoic acid.

Definition

ChEBI: 2,3-dihydroxybenzaldehyde is a dihydroxybenzaldehyde.

General Description

Electrochemical oxidation of 2,3-dihydroxybenzaldehyde in methanol at various pH has been studied using cyclic voltammetry and controlled-potential coulometry.

Synthesis

The general procedure for the synthesis of 2,3-dihydroxybenzaldehyde from o-vanillin was as follows: acetonitrile (40 ml) was added to a 100 ml aubergine flask, followed by sequential addition of aluminum trichloride (0.752 g, 5.64 mmol, 1.1 equiv), sodium iodide (2.305 g, 15.38 mmol, 3.0 equiv) and o-vanillin (0.780 g, 5.13 mmol). The reaction mixture was heated to 80 °C and the reaction was stirred for 18 hours. After completion of the reaction, the heating was stopped and cooled to room temperature. The reaction solution was acidified with 2 mol/L dilute hydrochloric acid (10 ml) and subsequently extracted with ethyl acetate (50 ml x 3). The organic phases were combined and washed sequentially with saturated aqueous sodium thiosulfate (10 ml) and saturated brine (10 ml). The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography afforded 2,3-dihydroxybenzaldehyde (0.620 g, yellow solid, 87% yield).

Purification Methods

Crystallise the aldehyde from water. [Beilstein 8 III 1979.]

References

[1] Patent: CN108821955, 2018, A. Location in patent: Paragraph 0021; 0022; 0025; 0026
[2] Patent: CN108178753, 2018, A. Location in patent: Paragraph 0023-0025
[3] Journal of the American Chemical Society, 2007, vol. 129, # 45, p. 13808 - 13809
[4] Patent: CN106699722, 2017, A. Location in patent: Paragraph 0050-0052
[5] Patent: CN107840845, 2018, A. Location in patent: Paragraph 0179; 0180; 0181; 0182

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