2-HYDROXY-3-METHOXY-5-NITROBENZALDEHYDE Chemical Properties

Melting point:

141-143 °C (lit.)

Boiling point:

344.0±42.0 °C(Predicted)

Density 

1.456

storage temp. 

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

form 

powder to crystal

pka

5.08±0.44(Predicted)

color 

Light orange to Yellow to Green

Water Solubility 

Slightly soluble in water.

Sensitive 

Air Sensitive

BRN 

613271

CAS DataBase Reference

17028-61-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2913.00.4000

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-HYDROXY-3-METHOXY-5-NITROBENZALDEHYDE Usage And Synthesis

Uses

2-Hydroxy-3-methoxy-5-nitrobenzaldehyde is used for the syntheses of zinc-selective spiropyran-based fluorescent and photoregenerable receptor, (E)-2,4-dihydroxy-N?-(2-hydroxy-3-methoxy-5-nitrobenzylidene)benzohydrazide dihydrate, ethyl 4-(8-methoxy-3?,3?-dimethyl-6-nitrospiro[chromene-2,2?-indoline]-1?-yl)butanoate and 1-(3-carbomethoxypropyl)-3-3-dimethyl-8-methoxy-6-nitrospiro[2H-1]-benzopyran-2,2-indoline.

Synthesis

General procedure for the synthesis of 2-hydroxy-3-methoxy-5-nitrobenzaldehyde from o-vanillin: o-vanillin (94 mg, 1 mmol) was dissolved in 3 mL of glacial acetic acid in a 50 mL test tube. Subsequently, solid Y(NO3)3-6H2O (383 mg, 1 mmol) was added to the solution and the reaction mixture was shaken continuously for 10 min at room temperature. The reaction process was monitored by thin layer chromatography (TLC) and the unfolding agent was petroleum ether with 10% ethyl acetate. Upon completion of the reaction, 30 mL of ice-cold water was added to the reaction mixture and allowed to stand for 15 min. The precipitated solid product was collected by filtration and washed with cold water. The solid product obtained was used directly for analysis without further purification. Detailed experimental methods for the synthesis of compounds 2a-2e are described in Supporting Information.

References

[1] Journal of Chemical Sciences, 2017, vol. 129, # 1, p. 39 - 43
[2] Journal of Materials Chemistry C, 2018, vol. 6, # 43, p. 11536 - 11551
[3] Dyes and Pigments, 2017, vol. 136, p. 292 - 301
[4] Proceedings of the National Institute of Sciences of India, 1940, vol. 6, p. 641,656
[5] Justus Liebigs Annalen der Chemie, 1932, vol. 496, p. 125,140

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