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4-(Aminomethyl)benzonitrile hydrochloride

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CAS:15996-76-6

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4-(Aminomethyl)benzonitrile hydrochloride Basic information
Product Name:4-(Aminomethyl)benzonitrile hydrochloride
Synonyms:4-CyanobenzylaMine HCl Salt;4-(Aminomethyl)benzonitrile hydrochloride 97%;4-(Aminomethyl)benzonitrile hydrochloride, >=99%;α-Amino-p-tolunitrile Hydrochloride;4-CNBAM X HCL;4-CYANOBENZYLAMINE HYDROCHLORIDE;4-(AMINOMETHYL)BENZONITRILE HCL;4-(AMINOMETHYL)BENZONITRILE HYDROCHLORIDE
CAS:15996-76-6
MF:C8H9ClN2
MW:168.62
EINECS:
Product Categories:Anilines, Aromatic Amines and Nitro Compounds;Nitrile
Mol File:15996-76-6.mol
4-(Aminomethyl)benzonitrile hydrochloride Structure
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 Reference15996-76-6(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 Information
ProviderLanguage
SigmaAldrich English
4-(Aminomethyl)benzonitrile hydrochloride Usage And Synthesis
Chemical PropertiesSolid
Uses4-(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
4-Cyanobenzylamine

10406-25-4

4-(Aminomethyl)benzonitrile hydrochloride

15996-76-6

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
4-(Aminomethyl)benzonitrile hydrochloride Preparation Products And Raw materials
Raw materials4-Cyanobenzylamine-->Ethyl acetate-->Hydrochloric acid
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