4-Morpholinobenzaldehyde Chemical Properties

Melting point:

65-69 °C

Boiling point:

365.5±37.0 °C(Predicted)

Density 

1.163±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

1.87±0.40(Predicted)

color 

Light yellow to Yellow to Orange

CAS DataBase Reference

1204-86-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29349990

4-Morpholinobenzaldehyde Usage And Synthesis

Uses

4-Morpholinobenzaldehyde is mainly used as a raw material for organic synthesis. It can be used to prepare dihydrotetrazolopyrimidine derivatives (ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate), coumarin-based chalcone derivatives ((E)-3-[3-(4-(4-morpholinophenyl)acryloyl]-2H-chromen-2-one) and Ru(II) polypyridine complexes, among others.

Synthesis

General procedure for the synthesis of 4-(4-morpholine)benzaldehyde from morpholine and p-fluorobenzaldehyde: In a dry reaction flask, p-fluorobenzaldehyde (25.0 g, 0.200 mol), morpholine (0.300 mol), and anhydrous potassium carbonate (40.0 g) were dissolved in N,N-dimethylformamide (DMF, 300 mL), and a catalytic amount of Aliquat 336 reagent. The reaction mixture was stirred at reflux for 24 hours at 100°C. Upon completion of the reaction, the mixture was concentrated to dryness under reduced pressure and cooled to room temperature. Subsequently, the concentrate was slowly poured into ice water and allowed to stand overnight. The precipitated solid was collected by filtration, washed with water and recrystallized with methanol to afford the target compound 4-morpholino benzaldehyde (Id) in 89% yield as yellow crystals with a melting point of 69 °C (in agreement with literature reports) [49,50].

References

[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2747 - 2759
[2] Bioorganic Chemistry, 2014, vol. 57, p. 65 - 82
[3] European Journal of Medicinal Chemistry, 2018, vol. 144, p. 68 - 81
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 12, p. 3721 - 3725
[5] Russian Journal of General Chemistry, 2013, vol. 83, # 10, p. 1864 - 1868

4-Morpholinobenzaldehyde(1204-86-0)Related Product Information

• Moroxydine hydrochloride
• Benzaldehyde
• Moroxydine
• Dimethomorph
• Tridemorph
• morpholine
• 2-Benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone
• 4-Morpholinobenzoic acid
• 4-MORPHOLINOACETOPHENONE
• 4-(4-MORPHOLINO)-3-NITROBENZALDEHYDE
• 3-MORPHOLINOBENZALDEHYDE
• 2-MORPHOLINOBENZALDEHYDE
• 1-(4-MORPHOLINO-3-NITROPHENYL)-1-ETHANONE
• 4-MORPHOLINOBENZOPHENONE
• 4-MORPHOLIN-4-YL-3-NITRO-BENZOIC ACID
• 2-HYDROXY-4-MORPHOLIN-4-YL-BENZALDEHYDE
• AKOS 91792
• 3-AMINO-4-MORPHOLIN-4-YL-BENZOIC ACID ETHYL ESTER