4-(Aminomethyl)benzonitrile hydrochloride Chemical Properties

Melting point:

274-279 °C(lit.)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly)

form 

Solid

color 

Off-White to Yellow

Water Solubility 

almost transparency

CAS DataBase Reference

15996-76-6(CAS DataBase Reference)

Safety Information

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

22-24/25-36/37-26

WGK Germany 

3

HS Code 

29269090

MSDS

• Language:English Provider:SigmaAldrich

4-(Aminomethyl)benzonitrile hydrochloride Usage And Synthesis

Chemical Properties

Solid

Uses

4-(Aminomethyl)benzonitrile hydrochloride can be used in the synthesis of fluorescent-labeled bisbenzamidine, which can be a biochemical tool in biomedical studies. It can also be used in the synthesis of 3-(p-benzylamino)-1,2,4,5 tetrazine, used in the modification of alginate hydrogels, employed in cell engineering applications.

Synthesis

In a 200 mL four-neck flask equipped with a stirrer, a thermometer, a gas introduction tube, and a reflux condenser, 4-cyanobenzylamine (10.0 g) obtained in Preparation Example 3 was dissolved in ethyl acetate (90.0 g). The reactor was cooled in a water bath under stirring while hydrogen chloride gas was slowly introduced into the gas phase of the reactor. Immediately after the introduction of hydrogen chloride gas, an exothermic phenomenon was observed and a white solid precipitated. After the reaction mixture was cooled to room temperature, the white solid was separated by filtration and dried in a vacuum desiccator to give 12.6 g of 4-(aminomethyl)benzonitrile hydrochloride (99% yield as 4-cyanobenzylamine). The resulting 4-(aminomethyl)benzonitrile hydrochloride was analyzed by high performance liquid chromatography and found to contain 77 wt% of 4-cyanobenzylamine. In addition, anion chromatographic analysis showed 23 wt% of hydrogen chloride in 4-(aminomethyl)benzonitrile hydrochloride. The measured bulk density of 4-(aminomethyl)benzonitrile hydrochloride was 0.3 g/mL.

References

[1] Patent: US6392083, 2002, B1. Location in patent: Page column 6
[2] Patent: US6392083, 2002, B1. Location in patent: Page column 7

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