3906-16-9

Basic information

• Product Name: (R)-(+)-1-(2-NAPHTHYL)ETHYLAMINE
• Synonyms: (R)-(+)-A-(2-NAPHTHYL)ETHYLAMINE;(R)-(+)-1-(2-NAPHTHYL)ETHYLAMINE;(R)-1-(2-NAPHTHYL)ETHYLAMINE;(R)-1-(NAPHTHALEN-2-YL)ETHANAMINE;(R)-(+)-α-Methyl-2-naphthalenemethylamine;(R)-(+)-1-(2-NAPHTHYL)ETHYLAMINE, CHIPROS 99+%, EE 99+%;(R)-2-(1-Aminoethyl)naphthalene;(1R)-1-(naphthalen-2-yl)ethan-1-amine
• CAS NO: 3906-16-9
• Molecular Formula: C₁₂H₁₃N
• Molecular Weight: 171.24
• Product Categories: Amines (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry
• Mol File: 3906-16-9.mol
• Article Data: 62

Chemical Properties

• Melting Point: 47-50 °C
• Boiling Point: 90°C 0,15mm
• Flash Point: 90°C/0.15mm
• Appearance: /
• Density: 1.411 g/cm³
• Vapor Pressure: 0.00108mmHg at 25°C
• Refractive Index: 22 ° (C=1, MeOH)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 9.36±0.40(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 3195950
• CAS DataBase Reference: (R)-(+)-1-(2-NAPHTHYL)ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1-(2-NAPHTHYL)ETHYLAMINE(3906-16-9)
• EPA Substance Registry System: (R)-(+)-1-(2-NAPHTHYL)ETHYLAMINE(3906-16-9)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-51/53
• Safety Statements: 26-36-61
• RIDADR: 3259
• WGK Germany: 3
• F: 10-34
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 3906-16-9(Hazardous Substances Data)

Usage

Description

(R)-(+)-1-(2-NAPHTHYL)ETHYLAMINE is an organic compound with a unique molecular structure that features a naphthyl group attached to an ethylamine chain. It is characterized by its chiral center, which gives it distinct stereochemistry and potential applications in various fields.

Uses

Used in Chemical Synthesis:
(R)-(+)-1-(2-NAPHTHYL)ETHYLAMINE is used as a chiral building block for the synthesis of various complex organic molecules. Its unique structure and stereochemistry make it a valuable component in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (R)-(+)-1-(2-NAPHTHYL)ETHYLAMINE is used as a key intermediate in the development of new drugs. Its chiral nature allows for the creation of enantiomerically pure compounds, which can have significant differences in biological activity and safety profiles.
Used in Aldol Reactions:
(R)-(+)-1-(2-NAPHTHYL)ETHYLAMINE is used as a reactant in aldol reactions, which are important carbon-carbon bond-forming processes in organic chemistry. These reactions are widely used in the synthesis of natural products, pharmaceuticals, and other complex molecules.
Used in Reactions with Amidocuprates:
(R)-(+)-1-(2-NAPHTHYL)ETHYLAMINE is also utilized in reactions with amidocuprates, which are organocopper reagents used in organic synthesis. These reactions can lead to the formation of new carbon-carbon bonds and the creation of diverse molecular structures with potential applications in various industries.

InChI:InChI=1/C12H13N/c1-9(13)11-7-6-10-4-2-3-5-12(10)8-11/h2-9H,13H2,1H3/t9-/m1/s1

Upstream product

• 273384-77-3 N-(1-Naphthalen-2-yl-ethyl)-formamide 
• 3082-62-0 (1S)-1-(2-naphthyl)ethylamine 
• 7228-47-9 2-(2-naphthyl)ethanol 
• 939-27-5 2-ethylnaphthalene 
• 1207946-35-7 (S)-2-methyl-N-(naphthalen-2-ylmethylene)propane-2-sulfinamide 
• 1201-74-7 1-(2-Naphthyl)ethylamine 
• 98-88-4 benzoyl chloride 
• 1165945-33-4 (R)-N-(2-methoxy-phenyl)-1-naphthalen-2-yl-ethylamine 
• 67021-79-8 (R)-α-(2-naphthyl)propionic acid 
• 93-08-3 methyl 2-naphthyl ketone 
• 27544-18-9 (S)-1-(2-Naphthyl)ethanol 
• 827-54-3 2-naphthylethylene 
• 176315-15-4 2-((R)-1-Azido-ethyl)-naphthalene 
• 142068-28-8 2-acetonaphthone benzoyl hydrazone 

Downstream Products

• 3082-62-0 (1S)-1-(2-naphthyl)ethylamine 
• 1201-74-7 (R)-[1-(naphthalen-2-yl)ethyl]amine 
• 100381-63-3 (+/-)-(1-[2]naphthyl-ethyl)-urea 
• 103280-28-0 1,4-bis-(1-[2]naphthyl-ethyl)-piperazine 
• 87783-03-7 Dodecanoic acid ((S)-1-naphthalen-2-yl-ethyl)-amide 
• 93-08-3 methyl 2-naphthyl ketone 

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.

Iterative Alanine Scanning Mutagenesis Confers Aromatic Ketone Specificity and Activity of L-Amine Dehydrogenases

Direct reductive amination of prochiral ketones catalyzed by amine dehydrogenases is attractive in the synthesis of active pharmaceutical ingredients. Here, we report the protein engineering of L-Bacillus cereus amine dehydrogenase to allow reactivity on synthetically useful aromatic ketone substrates using an iterative, multiple-site alanine scanning mutagenesis approach. Mutagenesis libraries based on molecular docking, iterative alanine scanning, and double-proximity filter approach significantly expand the scope of active pharmaceutical ingredients relevant building blocks. The eventual quintuple mutant (A115G/T136A/L42A/V296A/V293A) showed reactivity toward aromatic ketones 12 a (5-phenyl-pentan-2-one) and 13 a (6-phenyl-hexan-2-one), which have not been reported to serve as targets of reductive amination by currently available amine dehydrogenases. Docking simulation and tunnel analysis provided valuable insights into the source of the acquired specificity and activity.

Rh(III)-catalyzed synthesis of isoquinolines using the N-Cl bond of N-chloroimines as an internal oxidant

The Rh(III)-catalyzed coupling of N-chloroimines with alkynes for the efficient synthesis of isoquinolines is reported. This represents the first use of the N-Cl bond of N-chloroimines as an internal oxidant for construction of the isoquinoline skeleton. The synthesis features atom and step economy, a green solvent (EtOH), mild reaction conditions, and a broad substrate scope.