4-(MORPHOLINOMETHYL)BENZONITRILE

4-(MORPHOLINOMETHYL)BENZONITRILE Property

Melting point:

84-89°C

Boiling point:

332.4±32.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

5.94±0.10(Predicted)

form 

Crystalline Powder

color 

White to light yellow

CAS DataBase Reference

37812-51-4

Safety

HazardClass 

IRRITANT

HS Code 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H314Causes severe skin burns and eye damage

H318Causes serious eye damage

Precautionary statements

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

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

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

4-(MORPHOLINOMETHYL)BENZONITRILE Chemical Properties,Usage,Production

Chemical Properties

white to light yellow crystalline powder

Synthesis

1. 4-Cyanobenzyl bromide (2.28 g, 11.6 mmol) was dissolved in 25 mL of anhydrous acetonitrile under nitrogen protection. 2. To the above solution, morpholine (1.5 mL, 17.4 mmol) and potassium carbonate (0.69 g, 5 mmol) were added sequentially. 3. Stir the reaction mixture for 30 minutes at room temperature. 4. 4. Upon completion of the reaction, the reaction was quenched with water and extracted with ethyl acetate. 5. The organic layers were combined, dried over anhydrous magnesium sulfate and subsequently concentrated under reduced pressure. 6. 6. The crude product was purified by column chromatography (eluent: hexane-30% ethyl acetate/hexane) to give 4-(4-morpholinylmethyl)benzonitrile. 7. The product was a white solid. 7. The product was a white solid in 96% yield. 8. 8. 1H NMR (400 MHz, CDCl3) δ 7.61 (d, J = 7.9 Hz, 2H), 7.48 (d, J = 8.0 Hz, 2H), 3.71 (s, 4H), 3.55 (s, 2H), 2.44 (s, 4H); 13C NMR (100 MHz, CDCl3): 144.2, 132.5, 129.8, 119.2, 129.8, 119.2 129.8, 119.2, 111.3, 67.2, 63.1, 54.1.

References

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 1844 - 1857
[2] Patent: WO2012/69856, 2012, A1. Location in patent: Page/Page column 67
[3] European Journal of Medicinal Chemistry, 2018, vol. 152, p. 31 - 52
[4] Patent: WO2013/153357, 2013, A1. Location in patent: Page/Page column 20; 41; 42
[5] Patent: US2015/45354, 2015, A1. Location in patent: Paragraph 0251-0254