3,5-DIMETHYL-4-METHOXYBENZALDEHYDE

3,5-DIMETHYL-4-METHOXYBENZALDEHYDE Property

Boiling point:

264.0±35.0 °C(Predicted)

Density 

1.041±0.06 g/cm3(Predicted)

storage temp. 

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

Appearance

Light yellow to yellow Liquid

CAS DataBase Reference

39250-90-3(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn

HazardClass 

IRRITANT

HS Code 

2913000090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

3,5-DIMETHYL-4-METHOXYBENZALDEHYDE Chemical Properties,Usage,Production

Synthesis

The reaction was carried out by dissolving 3,5-dimethyl-4-hydroxybenzaldehyde (1.54 g, 10.3 mmol), iodomethane (0.77 mL, 12.4 mmol), and potassium carbonate (K2CO3, 1.71 g, 12.4 mmol) in N,N-dimethylformamide (DMF, 10.0 mL) and stirring the reaction for 18 hours at room temperature. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (EtOAc, 100 mL) and washed sequentially with water (2 x 25 mL) and saturated saline (25 mL). The organic phase was dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. Purification by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 9:1, v/v) afforded 3,5-dimethyl-4-methoxybenzaldehyde as a white solid (1.60 g, 95% yield). The structure of the product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H-NMR, 500 MHz, CDCl3) and carbon spectroscopy (13C-NMR, 125 MHz, CDCl3): 1H-NMR δ 9.88 (s, 1H), 7.56 (s, 2H), 3.78 (s, 3H), 2.35 (s, 6H); 13C-NMR δ 191.69,. 162.41, 132.25, 131.94, 130.73, 59.71, 16.19. Gas chromatography-mass spectrometry (GC-MS) showed the molecular ion peak m/z 163 [M+H]+, which is consistent with the theoretical value of molecular formula C10H12O2. Reversed-phase high performance liquid chromatography (RP-HPLC) analysis showed that the purity of the product was greater than 99%.

References

[1] Journal of Medicinal Chemistry, 2008, vol. 51, # 20, p. 6348 - 6358
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3441 - 3449
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 19, p. 4630 - 4637
[4] Angewandte Chemie - International Edition, 2014, vol. 53, # 41, p. 11056 - 11059
[5] Angew. Chem., 2015, vol. 126, # 41, p. 11236 - 11239,4