86225-78-7

Basic information

• Product Name: Benzonitrile, 4-(1-aminoethyl)-
• Synonyms: Benzonitrile, 4-(1-aminoethyl)-;4-(1-AMinoethyl)-benzonitrile HCl;4-(1-Aminomethyl)benzonitrile
• CAS NO: 86225-78-7
• Molecular Formula: C₉H₁₀N₂
• Molecular Weight: 146.1891
• Mol File: 86225-78-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 273.7±23.0 °C(Predicted)
• Appearance: /
• Density: 1.06±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 8.42±0.10(Predicted)
• CAS DataBase Reference: Benzonitrile, 4-(1-aminoethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-(1-aminoethyl)-(86225-78-7)
• EPA Substance Registry System: Benzonitrile, 4-(1-aminoethyl)-(86225-78-7)

Safety Data

• Hazardous Substances Data: 86225-78-7(Hazardous Substances Data)

Usage

General Description

Benzonitrile, 4-(1-aminoethyl)-, also known as N-(4-cyanophenyl)ethan-1-amine, is an organic compound with the molecular formula C9H9N. It is a clear, colorless to pale yellow liquid with a faint odor, and it is commonly used in the synthesis of pharmaceuticals, dyes, and other chemical products. It is classified as a primary aromatic amine, and it contains a nitrile functional group, which makes it a valuable intermediate in the production of various chemical compounds. This chemical is often used in research and industrial applications, and it is important to handle it with caution due to its potential health hazards.

InChI:InChI=1S/C9H10N2/c1-7(11)9-4-2-8(6-10)3-5-9/h2-5,7H,11H2,1H3

Upstream product

• 1443-80-7 4-cyanophenyl methyl ketone 

Downstream Products

• 182159-22-4 Boc-D-phenylalanyl-proline (D,L)-α-methyl-4-cyanobenzylamide 
• 173898-21-0 4-(1-aminoethyl)benzamide 
• 1571135-28-8 1-[1-(4-cyanophenyl)ethyl]-6-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acid 
• 1355158-76-7 tert-butyl [1-(4-cyanophenyl)ethyl]carbamate 
• 199442-00-7 N-((R)-1-(4-cyanophenyl)ethyl)acetamide 

Relevant articles and documents

Air Stable Iridium Catalysts for Direct Reductive Amination of Ketones

Half-sandwich iridium complexes bearing bidentate urea-phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. One of the complexes was found to be active in both the Leuckart–Wallach (NH4CO2H) type reaction as well as in the hydrogenative (H2/NH4AcO) reductive amination. The protocol with ammonium formate does not require an inert atmosphere, dry solvents, as well as additives and in contrast to previous reports takes place in hexafluoroisopropanol (HFIP) instead of methanol. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α-position.

Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions

The conversion of aldehydes and ketones to 1° amines could be promoted by half-sandwich iridium complexes using ammonium formate as both the nitrogen and hydride source. To optimize this method for green chemical synthesis, we tested various carbonyl substrates in common polar solvents at physiological temperature (37 °C) and ambient pressure. We found that in methanol, excellent selectivity for the amine over alcohol/amide products could be achieved for a broad assortment of carbonyl-containing compounds. In aqueous media, selective reduction of carbonyls to 1° amines was achieved in the absence of acids. Unfortunately, at Ir catalyst concentrations of 1 mM in water, reductive amination efficiency dropped significantly, which suggest that this catalytic methodology might be not suitable for aqueous applications where very low catalyst concentration is required (e.g., inside living cells).

Rh(III)-Catalyzed Coupling of N-Chloroimines with α-Diazo-α-phosphonoacetates for the Synthesis of 2 H-Isoindoles

We report herein the first use of N-chloroimines as effective synthons for directed C-H functionalization. Rh(III)-catalyzed coupling of N-chloroimines with α-diazo-α-phosphonoacetates allows for efficient dechlorinative/dephosphonative access to 2H-isoindoles. Further deesterification under Ni(II) catalysis enables the complete elimination of reactivity-assisting groups and full exposure of reactivity of C3 and N2 ring atoms for attaching structurally distinct appendages.