2,4-Dihydroxy-3-methylbenzaldehyde Chemical Properties

Melting point:

150 °C

Boiling point:

345.7±12.0 °C(Predicted)

Density 

1.331±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

7.93±0.23(Predicted)

color 

Light Orange to Light Red

InChI

InChI=1S/C8H8O3/c1-5-7(10)3-2-6(4-9)8(5)11/h2-4,10-11H,1H3

InChIKey

AOPMHYFEQDBXPZ-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(O)C(C)=C1O

LogP

1.727 (est)

EPA Substance Registry System

Benzaldehyde, 2,4-dihydroxy-3-methyl- (6248-20-0)

Safety Information

Safety Statements 

24/25

HS Code 

29124990

2,4-Dihydroxy-3-methylbenzaldehyde Usage And Synthesis

Uses

4-Formyl-2-methylresorcinol is a reactant in the synthesis of 3-benzo[b]thiophenecoumarin, with potent anti-proliferative activity against breast cancer cell lines

Synthesis

The general procedure for the synthesis of 3-methyl-2,4-dihydroxybenzaldehyde from 2,6-dihydroxytoluene and N,N-dimethylformamide was as follows: first, N,N-dimethylformamide (6.2 mL, 80.65 mmol) was mixed with phosphorochloride (8.1 mL, 88.61 mmol), followed by the addition of 2-methylresorcinol (5.0 g, 40.3 mmol ) and ethyl acetate (100 mL). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the reaction solution was combined with ethyl acetate, the organic phase was dried with anhydrous sodium sulfate, filtered to remove the desiccant, and the filtrate was subsequently concentrated under reduced pressure. Finally, the target product 3-methyl-2,4-dihydroxybenzaldehyde (4.9 g, 79.9% yield) was purified by silica gel column chromatography.

References

[1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 12, p. 2305 - 2309
[2] Chemistry - An Asian Journal, 2010, vol. 5, # 1, p. 130 - 140
[3] Patent: CN106957279, 2017, A. Location in patent: Paragraph 0042; 0049; 0050; 0051
[4] Tetrahedron Letters, 2000, vol. 41, # 11, p. 1741 - 1745
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 12888 - 12891

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