3-FORMYL-4-HYDROXYBENZOIC ACID Chemical Properties

Melting point:

246-250 °C (lit.)

Boiling point:

254.32°C (rough estimate)

Density 

1.3579 (rough estimate)

refractive index 

1.5090 (estimate)

storage temp. 

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

form 

solid

pka

4.22±0.10(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C8H6O4/c9-4-6-3-5(8(11)12)1-2-7(6)10/h1-4,10H,(H,11,12)

InChIKey

NXZBZWZORYEIJL-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/38

Safety Statements 

26-36/37

WGK Germany 

2

HS Code 

2918999090

MSDS

• Language:English Provider:SigmaAldrich

3-FORMYL-4-HYDROXYBENZOIC ACID Usage And Synthesis

Synthesis

GENERAL METHOD: To a solution of trifluoroacetic acid (5 mL) of the substrate (1a-1q, 0.15 mmol) was sequentially added hexamethylenetetramine (urotropine, 0.3 mmol) and cuprous oxide (0.15 mmol). The reaction mixture was heated to reflux for 5 h and subsequently cooled to room temperature. A 3 N hydrochloric acid solution (5 mL) was slowly added to the reaction system and stirring was continued for 1 hour. Upon completion of the reaction, the mixture was concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography (200-300 mesh) to afford the target product 3-formyl-4-hydroxybenzoic acid.

References

[1] Bioconjugate Chemistry, 2018, vol. 29, # 9, p. 2909 - 2919
[2] Dalton Transactions, 2010, vol. 39, # 8, p. 2070 - 2077
[3] European Journal of Inorganic Chemistry, 2012, # 32, p. 5225 - 5238
[4] Research on Chemical Intermediates, 2015, vol. 41, # 11, p. 8147 - 8158
[5] Chemical Communications, 2018, vol. 54, # 42, p. 5385 - 5388

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