3082-62-0

Basic information

• Product Name: (S)-(-)-1-(2-Naphthyl)ethylamine
• Synonyms: (S)-(-)-1-(2-NAPHTHYL)ETHYLAMINE;(S)-1-(2-NAPHTHYL)ETHYLAMINE;(S)-1-(NAPHTHALEN-2-YL)ETHANAMINE;(S)-(-)-A-(2-NAPHTHYL)ETHYLAMINE;(s)-(-)-α-methyl-2-naphthalenemethylamine;(S)-(-)-1-(2-NAPHTHYL)ETHYLAMINE: CHIPROS 99%, EE 99%;(S)-(-)-1-(2-NAPHTHYL)ETHYLAMINE, CHIPROS 99+%, EE 99+%;(S)-2-(1-Aminoethyl)naphthalene
• CAS NO: 3082-62-0
• Molecular Formula: C₁₂H₁₃N
• Molecular Weight: 171.24
• EINECS: -0
• Product Categories: Amines (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry
• Mol File: 3082-62-0.mol
• Article Data: 70

Chemical Properties

• Melting Point: 47-50 °C
• Boiling Point: 90°C 0,15mm
• Flash Point: 90°C/0.15mm
• Appearance: /
• Density: 1.064 g/cm³
• Vapor Pressure: 0.00108mmHg at 25°C
• Refractive Index: -20 ° (C=1, MeOH)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 9.36±0.40(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 3195949
• CAS DataBase Reference: (S)-(-)-1-(2-Naphthyl)ethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1-(2-Naphthyl)ethylamine(3082-62-0)
• EPA Substance Registry System: (S)-(-)-1-(2-Naphthyl)ethylamine(3082-62-0)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-51/53
• Safety Statements: 26-36-61
• RIDADR: 2923
• WGK Germany: 3
• F: 10-34
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 3082-62-0(Hazardous Substances Data)

Usage

Description

(S)-(-)-1-(2-Naphthyl)ethylamine is an organic compound with the molecular formula C12H11N. It is a chiral molecule, featuring a naphthyl group attached to an ethylamine backbone. (S)-(-)-1-(2-Naphthyl)ethylamine is known for its applications in various chemical reactions and processes due to its unique structural properties.

Uses

Used in Asymmetric Synthesis:
(S)-(-)-1-(2-Naphthyl)ethylamine is used as a chiral auxiliary in asymmetric synthesis for the production of enantiomerically pure compounds. Its presence in the reaction can help control the stereochemistry of the product, leading to a higher yield of the desired enantiomer.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-(-)-1-(2-Naphthyl)ethylamine is used as a chiral building block for the synthesis of various drugs. Its unique structure allows for the creation of novel compounds with specific biological activities, contributing to the development of new medications.
Used in Chemical Catalysts:
(S)-(-)-1-(2-Naphthyl)ethylamine is used as a bifunctional catalyst in the Strecker and nitro-Michael reactions. Its chiral nature enables it to selectively catalyze these reactions, leading to the formation of specific products with high enantiomeric purity.
Used in Chiral Resolution:
(S)-(-)-1-(2-Naphthyl)ethylamine is also employed as a chiral resolution reagent. It can be used to separate enantiomers of a racemic mixture, allowing for the isolation of individual enantiomers with high purity. This is particularly important in the synthesis of chiral drugs, where the desired biological activity is often associated with a specific enantiomer.
Used in Thiourea Compound Preparation:
(S)-(-)-1-(2-Naphthyl)ethylamine is used in the preparation of thiourea compounds using chiral amine. These thiourea compounds find applications in various fields, including agriculture, pharmaceuticals, and materials science, due to their diverse chemical properties and reactivity.

InChI:InChI=1/C12H13N/c1-9(13)11-7-6-10-4-2-3-5-12(10)8-11/h2-9H,13H2,1H3/t9-/m0/s1

Upstream product

• 100485-52-7 1-(naphthyl-⁽²⁾)-ethanone-⁽¹⁾-seqtrans-oxime 
• 540-69-2 ammonium formate 
• 77287-34-4 formamide 
• 93-08-3 methyl 2-naphthyl ketone 
• 16712-16-6 ammonium formate 
• 492-41-1 (1R,2S)-norephedrine 
• 51705-89-6 Z de l'ether methylique de l'oxime de l'acetyl-2 naphthalene 
• 827-54-3 2-naphthylethylene 
• 1201-74-7 1-(2-Naphthyl)ethylamine 
• 98-88-4 benzoyl chloride 
• 87783-01-5 (S)-N-acetyl-1-(2-naphthyl)ethylamine 
• 939-27-5 2-ethylnaphthalene 
• 1207946-35-7 (S)-2-methyl-N-(naphthalen-2-ylmethylene)propane-2-sulfinamide 
• 7228-47-9 2-(2-naphthyl)ethanol 

Downstream Products

• 100381-63-3 (S)-(1-[2]naphthyl-ethyl)-urea 
• 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 
• 87783-01-5 (S)-N-acetyl-1-(2-naphthyl)ethylamine 
• 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.