210488-53-2

Basic information

• Product Name: (R)-1-(4-CYANOPHENYL)ETHANAMINE
• Synonyms: (R)-1-(4-CYANOPHENYL)ETHANAMINE;Benzonitrile, 4-[(1R)-1-aminoethyl]-;(R)-(+)-1-(4-Cyanophenyl)ethylamine;(R)-4-(1-aminoethyl)benzonitrile
• CAS NO: 210488-53-2
• Molecular Formula: C9H10N2
• Molecular Weight: 146.19
• Product Categories: API intermediates
• Mol File: 210488-53-2.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 273.7°C at 760 mmHg
• Flash Point: 119.3°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 0.00565mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: (R)-1-(4-CYANOPHENYL)ETHANAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(4-CYANOPHENYL)ETHANAMINE(210488-53-2)
• EPA Substance Registry System: (R)-1-(4-CYANOPHENYL)ETHANAMINE(210488-53-2)

Safety Data

• Hazardous Substances Data: 210488-53-2(Hazardous Substances Data)

Usage

General Description

(R)-1-(4-cyanophenyl)ethanamine, also known as R-Phenylalanine, is a chemical compound with the molecular formula C9H11N. It is an organic compound that consists of a phenyl group attached to an ethanamine chain. (R)-1-(4-CYANOPHENYL)ETHANAMINE is an important building block in the synthesis of various pharmaceuticals and natural products. It is an enantiomer of phenylalanine, an essential amino acid that is found in proteins and plays a crucial role in the function of the nervous system. (R)-1-(4-cyanophenyl)ethanamine is often used in research and development to create new pharmaceutical drugs and to study the biological effects and mechanisms of action of various compounds.

InChI:InChI=1/C9H10N2/c1-7(11)9-4-2-8(6-10)3-5-9/h2-5,7H,11H2,1H3/t7-/m0/s1

Upstream product

• 1443-80-7 4-cyanophenyl methyl ketone 
• 105-07-7 4-cyanobenzaldehyde 
• 847729-63-9 tert-butyl N-[(1S)-1-(4-cyanophenyl)ethyl]carbamate 
• 186296-23-1 (S)-N-(1-(4-bromophenyl)ethyl)acetamide 
• 199441-99-1 (S)-N-ethanoyl-1-(4-cyanophenyl)ethylamine 
• 24358-62-1 (R)-1-(4-bromophenyl)ethylamine 
• 27298-97-1 (S)-1-(4-bromophenyl)ethylamine 

Downstream Products

• 1362627-43-7 C₂₃H₂₉N₃O₃ 

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.