4-(1-PYRROLIDINYL)BENZONITRILE Chemical Properties

Melting point:

200 °C

Boiling point:

117 °C

Density 

1.12±0.1 g/cm3(Predicted)

storage temp. 

Store at room temperature

solubility 

soluble in Methanol

pka

5.68±0.20(Predicted)

form 

Solid

color 

Off-white

λmax

296nm(CH3CN)(lit.)

InChI

InChI=1S/C11H12N2/c12-9-10-3-5-11(6-4-10)13-7-1-2-8-13/h3-6H,1-2,7-8H2

InChIKey

ZNMSYUCZLWETII-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(N2CCCC2)C=C1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

RIDADR 

UN 3439 6.1/PG III

HazardClass 

6.1

PackingGroup 

III

HS Code 

2933998090

4-(1-PYRROLIDINYL)BENZONITRILE Usage And Synthesis

Uses

4-(Pyrrolidin-1-yl)benzonitrile is a useful research chemical.

Synthesis

In a 10 mL conical flask, p-chlorobenzonitrile (1 mmol), tetrahydropyrrole (3 mmol), K2CO3 (2 mmol), and Pd-PFMN catalyst (0.06 g, 1.2 mol%) were added, and the mixture was stirred for 24 hours at room temperature. Upon completion of the reaction, the mixture was cooled to room temperature and the catalyst was removed by magnetic separation. The catalyst was subsequently washed with ether (2 × 10 mL) and deionized oxygen-free water (2 × 10 mL) and dried for next use. The aqueous phase was extracted with ether (2 × 10 mL), and the organic phases were combined and dried with Na2SO4. Finally, 4-(1-pyrrolidine)benzonitrile was purified by column chromatography (eluent: hexane/ethyl acetate).

References

[1] Journal of the Iranian Chemical Society, 2015, vol. 12, # 11, p. 2057 - 2064
[2] Journal of Organometallic Chemistry, 2017, vol. 831, p. 1 - 10
[3] Journal of the American Chemical Society, 2015, vol. 137, # 37, p. 11942 - 11945
[4] Tetrahedron Letters, 2003, vol. 44, # 10, p. 2217 - 2220
[5] Tetrahedron, 2008, vol. 64, # 23, p. 5604 - 5619

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