4-Morpholinobenzaldehyde

4-Morpholinobenzaldehyde Property

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H302Harmful if swallowed

H315Causes skin irritation

H317May cause an allergic skin reaction

H318Causes serious eye damage

H331Toxic if inhaled

H341Suspected of causing genetic defects

H351Suspected of causing cancer

H361Suspected of damaging fertility or the unborn child

H370Causes damage to organs

H372Causes damage to organs through prolonged or repeated exposure

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P260Do not breathe 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.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

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

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

P501Dispose of contents/container to..…

4-Morpholinobenzaldehyde Chemical Properties,Usage,Production

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