2,5-DIMETHOXY-4-METHYLBENZALDEHYDE Chemical Properties

Melting point:

82-86℃

Boiling point:

102 °C(Press: 0.1 Torr)

Density 

1.089±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Dichloromethane, DMSO, Methanol

form 

Solid

color 

Off-white

Water Solubility 

Soluble in dichloromethane, dimethyl sulfoxide and methanol. Slightly soluble in water.

InChI

InChI=1S/C10H12O3/c1-7-4-10(13-3)8(6-11)5-9(7)12-2/h4-6H,1-3H3

InChIKey

LRSRTWLEJBIAIT-UHFFFAOYSA-N

SMILES

C(=O)C1=CC(OC)=C(C)C=C1OC

Safety Information

HS Code 

2912490090

2,5-DIMETHOXY-4-METHYLBENZALDEHYDE Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

2,5-Dimethoxy-4-methylbenzaldehyde is used in the preparation of phenylamine derivative as potential psychotomimetics.

Synthesis

At room temperature, 8.5 mL of N-methylformanilide (0.068 mol) was mixed with 6.3 mL of trichlorophosphorus (0.068 mol) and stirred for 40 minutes. Subsequently, 17.8 g of 2,5-dimethoxytoluene (0.117 mol) was added. The reaction mixture was heated to 50 °C and maintained for 6 hours. Upon completion of the reaction, it was cooled to 20 °C and hydrolyzed with 100 mL of 10% aqueous sodium acetate, followed by extraction with ether twice, combining the organic phases and concentrating. The residue was dissolved in aqueous sodium hydroxide and again extracted twice with ether. The aqueous phase was adjusted to pH=12 with base, and a white crystalline product 2,5-dimethoxy-4-toluylaldehyde was precipitated with a melting point of 83 °C and a yield of 67%.

References

[1] Journal of Organic Chemistry, 2012, vol. 77, # 18, p. 8231 - 8243
[2] Patent: US2004/43995, 2004, A1. Location in patent: Page 12
[3] Journal of Medicinal Chemistry, 1976, vol. 19, # 12, p. 1400 - 1404
[4] Patent: US2009/29976, 2009, A1. Location in patent: Page/Page column 22
[5] Patent: US2004/19091, 2004, A1. Location in patent: Page/Page column 6

2,5-DIMETHOXY-4-METHYLBENZALDEHYDE(4925-88-6)Related Product Information

• 2,5-dimethoxy-4-pentylbenzaldehyde
• 1,4-dimethoxy-2-pentylbenzene
• 2,5-DiMethoxy-1-propylbenzene
• 2-hexyl-1,4-dimethoxybenzene
• 2,5-diMethoxy-4-n-propylbenzaldehyde
• 2-Ethyl-1,4-dimethoxybenzene
• 2,5-Dimethoxytoluene
• 2-butyl-1,4-dimethoxybenzene
• 4-butyl-2,5-dimethoxybenzaldehyde
• 2-(sec-butyl)-1,4-dimethoxybenzene
• 2,5-DIMETHOXY-4-ETHYLBENZALDEHYDE
• 2-isobutyl-1,4-diMethoxybenzene