2,4-Dihydroxy-3-methylbenzaldehyde

2,4-Dihydroxy-3-methylbenzaldehyde Property

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

Safety Statements 

24/25

HS Code 

29124990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

2,4-Dihydroxy-3-methylbenzaldehyde Chemical Properties,Usage,Production

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