42882-31-5

Basic information

• Product Name: (+/-)1-(1-Naphthyl)ethylamine
• Synonyms: (±)-1-(1-Naphthyl)ethylamine,98%;1-Naphthaleneethylamine;1-Naphthalenemethanamine, .alpha.-methyl-;(n)-1-(1-naphthyl)ethylamine;(+/-)1-(1-Naphthyl)ethylamine;(±)-α-Methyl-1-naphthalenemethylamine, (±)-1-(1-Naphthyl)ethylamine;1-Naphthalen-1-ylethanamine;(±)-1-(1-Aminoethyl)naphthalene
• CAS NO: 42882-31-5
• Molecular Formula: C12H13N
• Molecular Weight: 171.24
• EINECS: 1308068-626-2
• Product Categories: Naphthalene series
• Mol File: 42882-31-5.mol

Chemical Properties

• Boiling Point: 156 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: colorless or yellow liquid
• Density: 1.063 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.621(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 9.26±0.40(Predicted)
• Sensitive: Air Sensitive
• BRN: 3197375
• CAS DataBase Reference: (+/-)1-(1-Naphthyl)ethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)1-(1-Naphthyl)ethylamine(42882-31-5)
• EPA Substance Registry System: (+/-)1-(1-Naphthyl)ethylamine(42882-31-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-34-25
• Safety Statements: 26-36-45-36/37/39
• RIDADR: 2735
• WGK Germany: 3
• F: 10-34
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 42882-31-5(Hazardous Substances Data)

Usage

Uses

Used in Enzymic Resolution of Amines:
(+/-)1-(1-Naphthyl)ethylamine is used as a chirality modifier in the enzymic resolution of amines. As a chirality modifier, it enhances the selectivity of enzymes towards specific enantiomers during the resolution process, leading to the production of enantiomerically pure compounds. This is particularly important in the pharmaceutical industry, where the desired biological activity is often associated with a single enantiomer.
Used in Surface Science Research:
In surface science, (+/-)1-(1-Naphthyl)ethylamine is utilized for studying the adsorption properties of organic molecules on metal surfaces, such as platinum. (+/-)1-(1-Naphthyl)ethylamine's interaction with these surfaces has been investigated using advanced techniques like reflection-absorption infrared spectroscopy and temperature-programmed desorption. These studies contribute to the understanding of molecular adsorption mechanisms and can be applied in various fields, including catalysis and materials science.
Used in Analytical Chemistry:
(+/-)1-(1-Naphthyl)ethylamine can also be employed as a reference compound in analytical chemistry for the development and validation of methods related to the detection and quantification of amines. Its unique properties make it a suitable candidate for calibrating instruments and establishing standard procedures in various analytical techniques.

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

Upstream product

• 75-31-0 isopropylamine 
• 3886-70-2 (R)-1-(1-Naphthyl)ethylamine 
• 10420-89-0 (S)-1-(1-Naphthyl)ethylamine 
• 344248-49-3 N-(1-naphthalen-1-yl-ethyl)-P,P-diphenylphosphinamide 
• 941-98-0 1'-naphthacetophenone 
• 1956-40-7 1-(1-naphthalenyl)ethanone oxime 
• 49681-33-6 N-formyl-1-naphthylethylamine 

Downstream Products

• 765219-14-5 (+/-)-N-(p-Aminophenylacetyl)-1-(1-naphthyl)ethylamin 
• 10420-89-0 (-)-α-(1-naphthyl)-ethylamine 
• 3309-13-5 (+)-α-1-(naphthyl)-ethylamine 
• 1517-69-7 (R)-1-phenylethanol 
• 72407-64-8 (1R)-N-acetyl-(1-naphthyl)ethylamine 
• 57605-95-5 1-(1-naphthyl)ethanol 
• 1243166-48-4 (1S)-1-(naphthalen-1-yl)ethanamine (R)-mandelate 
• 1073144-62-3 (1R)-1-(naphthalen-1-yl)ethanamine (R)-mandelate 
• 75-31-0 isopropylamine 
• 1416820-70-6 rosuvastatin 1-naphthalen-1-yl-ethylamine salt 
• 111782-25-3 1-(1-naphthalen-1-yl)-3-(4-nitrophenyl)thiourea 
• 178306-52-0 (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid 
• 1095393-70-6 N-((R)-1-naphthalen-1-yl-ethyl)-acrylamide 
• 10420-89-0 (S)-1-(1-Naphthyl)ethylamine 

Relevant articles and documents

Versatile Dynamic Covalent Assemblies for Probing π-Stacking and Chirality Induction from Homotopic Faces

Herein we report for the first time the use of dynamic covalent reactions (DCRs) for building a π-stacking model system and further quantifying its substituent effects (SEs), which remain a topic of debate despite the rich history of stacking. A general DCR between 10-methylacridinium ion and primary amines was discovered, in which π-stacking played a stabilizing role. Facile quantification of SEs with in situ competing π-stacking systems was next achieved in the form of amine exchange exhibiting structural diversity by simply varying components. The linear correlation with σm in Hammett plots indicates the dominance of purely electrostatic SEs, and the additivity of SEs is in line with the direct interaction model. With α-chiral amines π-stacking within the adduct enabled chirality transfer from homotopic faces. The strategy of dynamic covalent assembly should be appealing to future research of probing weak interactions and manipulating chirality.

Bioinspired organocatalytic aerobic C-H oxidation of amines with an ortho -quinone catalyst

A simple bioinspired ortho-quinone catalyst for the aerobic oxidative dehydrogenation of amines to imines is reported. Without any metal cocatalysts, the identified optimal ortho-quinone catalyst enables the oxidations of α-branched primary amines and cyclic secondary amines. Mechanistic studies have disclosed the origins of different performances of ortho-quinone vs para-quinone in biomimetic amine oxidations.

A Single Lipase-Catalysed One-Pot Protocol Combining Aminolysis Resolution and Aza-Michael Addition: An Easy and Efficient Way to Synthesise β-Amino Acid Esters

A novel one-pot protocol combining aza-Michael addition and aminolysis resolution was developed to obtain chiral β-amino acid esters with lipase B from Candida antarctica (CAL-B) as the only catalyst. This method is conducted under mild reaction conditions and is very easy to handle. After a series of detailed optimization studies, ten racemic aromatic or aliphatic amines were subjected to this one-pot procedure, and twelve chiral β-amino acid esters and ten chiral amides were successfully synthesised with excellent ee values in theoretical yields. Scaled-up procedures also worked without apparent reduction in reaction rate or enantioselectivity, which makes this method suitable for large-scale production of chiral β-amino acid esters. A one-pot protocol for simultaneous synthesis of chiral β-amino acid esters and amides was developed by combining single lipase B from Candida antarctica (CAL-B) catalysed aza-Michael addition and aminolysis resolution. This method requires mild reaction conditions and is very easy to handle. Chiral β-amino acid esters and chiral amides were obtained with excellent ee values and in theoretical yields.

Liquid chromatographic resolution of fendiline and its analogues on a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid

Fendiline, an effective anti-anginal drug for the treatment of coronary heart diseases, and its sixteen analogues were resolved on a CSP based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid. Fendiline was resolved quite well with the separation factor (α) of 1.25 and resolution (RS ) of 1.55 when a mobile phase consisting of methanol-acetonitrile-trifluoroacetic acid-triethylamine at a ratio of 80/20/0.1/0.5 (v/v/v/v) was used. The comparison of the chromatographic behaviors for the resolution of fendiline and its analogues indicated that the 3,3-diphenylpropyl group bonded to the secondary amino group of fendiline is important in the chiral recognition and the difference in the steric bulkiness between the phenyl group and the methyl group at the chiral center of fendiline is also important in the chiral recognition.

PROCESS FOR THE RACEMIZATION OF OPTICALLY ACTIVE ARYLALKYLAMINES

Many optically active amines are valuable pharmaceuticals and intermediates for the preparation of active compounds. It is frequently the case that only one of the two enantiomers is active or not harmful, so that isolation of this enantiomer from the racemic mixture is necessary. Processes for racemate resolution make it possible to separate racemic mixtures into their enantiomers. Here, it is useful to once again racemize the enantiomer which is not required and recirculate it to racemate resolution and thus improve the yield of the desired enantiomer. The present invention relates to processes for the racemization of optically active amines, in particular arylalkylamines, in the presence of hydrogen and a hydrogenation/dehydrogenation catalyst comprising nickel, cobalt and copper as active components at elevated temperature.

Efficient synthesis and practical resolution of 1-(naphthalen-1-yl) ethanamine, a key intermediate for cinacalcet

An efficient synthesis of 1-(naphthalen-1-yl)ethanamine (RS-2) and its practical resolution to optically pure (1R)-(naphthalen-1-yl)ethanamine (R-(+)-2), a key intermediate in the synthesis of cinacalcet hydrochloride (1), is described. The resolution of RS-2 using R-(-)-mandelic acid as a resolving agent in ethanol was established on an industrial scale to give pure R-(+)-2 with >99.8% ee after liberation of the amine from its mandelate salt. An efficient process for the racemization of undesired isomer S-(-)-2 is also provided to maximize the yield of desired enantiomer.

Reductive amination of ketones: Novel one-step transfer hydrogenations in batch and continuous-flow mode

Various ketones were efficiently transformed into the corresponding amines using ammonium formate in the presence of Zn dust or 10% Pd/C. The low-cost Zn dust method proved to be effective in amine formation from carbonyl groups at the benzylic side-chain position of aromatic systems, whereas 10% Pd/C was an efficient catalyst in the reductive aminations of carbonyl groups non-conjugated with any π-system. The 10% Pd/C-catalyzed reductions were performed more effectively in a continuous-flow X-Cube reactor than in the batch system.

Heterogeneous raney nickel and cobalt catalysts for racemization and dynamic kinetic resolution of amines

Raney metals were studied as heterogeneous catalysts for racemization and dynamic kinetic resolution (DKR) of chiral amines, as an alternative to metals like palladium or ruthenium. Both Raney nickel and cobalt were able to selectively racemize various chiral amines with high selectivity. In the racemization of benzylic primary amines, the minor formation of side products, e.g., secondary amines, can be suppressed by varying the hydrogen pressure. In the racemization of aliphatic amines over Raney catalysts, the selectivity is very high, with the enantiomeric amine as the sole product. DKR of racemic aliphatic amines can be performed with immobilized Candida antarctica lipase B and Raney nickel in one pot; for 2-hexylamine, a yield of 95% of the acetylated amide was achieved, with 97% ee. Attention is devoted to the compatibility of the enzyme and the metal catalyst during the DKR. For benzylic primary amines, a two-pot process is proposed in which the liquid is alternatingly shuttled between two vessels containing the solid racemization catalyst and the biocatalyst. After 4 such cycles, the amide of (R)-1-phenylethylamine was obtained with 94% yield and more than 90% ee.

PROCESSES FOR THE PREPARATION OF CINACALCET

There are described several processes for making a free base of cinacalcet. One of the described processes goes through an intermediate of the formula (II) where R1 and R2 are both hydrogen, or R1 and R2, together, form a double bond.

Arylalkylamine vanadium (V) salts for the treatment and/or prevention of Diabetes mellitus

This invention provides compounds of formula (IIA) and pharmaceutical compositions thereof, where M, a, b, and R1-R5 are as defined herein, for treating human type 1 and type 2 diabetes, particularly insulin-resistant diabetes. Pharmaceutical compositions comprising the compounds of formula (IIA) are also disclosed.