2217-40-5

Basic information

• Product Name: 1,2,3,4-Tetrahydro-1-naphthylamine
• Synonyms: 1-Naphthalenamine, 1,2,3,4-tetrahydro-;1-tetralinamine;2-Amino-1,2,3,4-tetrahydronaftalen [Czech];Aminotetralin [Czech];tetralin-1-ylamine;AKOS BBS-00003619;1,2,3,4-TETRAHYDRO-1-NAPHTHYLAMINE;1,2,3,4-TETRAHYDRO-NAPHTHALEN-1-YLAMINE
• CAS NO: 2217-40-5
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.22
• EINECS: 218-712-7
• Product Categories: Pyridines;Anilines, Aromatic Amines and Nitro Compounds;Amines;C9 to C10;Nitrogen Compounds;organic intermediates
• Mol File: 2217-40-5.mol
• Article Data: 37

Chemical Properties

• Boiling Point: 246-247 °C714 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.026 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0228mmHg at 25°C
• Refractive Index: n20/D 1.562(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 9.39±0.20(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 1,2,3,4-Tetrahydro-1-naphthylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-Tetrahydro-1-naphthylamine(2217-40-5)
• EPA Substance Registry System: 1,2,3,4-Tetrahydro-1-naphthylamine(2217-40-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 2217-40-5(Hazardous Substances Data)

Usage

Description

1,2,3,4-Tetrahydro-1-naphthylamine is an organic compound with the molecular formula C10H13N. It is a clear, colorless to yellow liquid and is known for its efficient reactivity in iodocyclization of 4-aryl-4-pentenoic acids. 1,2,3,4-Tetrahydro-1-naphthylamine has found applications in various industries, particularly in the synthesis of new chiral phosphine-aminophosphine ligands.

Uses

Used in Pharmaceutical Industry:
1,2,3,4-Tetrahydro-1-naphthylamine is used as a reagent for the iodocyclization of 4-aryl-4-pentenoic acids, which is a crucial step in the synthesis of various pharmaceutical compounds. Its efficiency in this process makes it a valuable component in the development of new drugs.
Used in Chemical Synthesis:
1,2,3,4-Tetrahydro-1-naphthylamine is used as a building block in the preparation of new chiral phosphine-aminophosphine ligands. These ligands are essential in various chemical reactions, particularly in asymmetric catalysis, where they help to achieve high selectivity and enantiomeric excess.
Used in Research and Development:
Due to its unique chemical properties and reactivity, 1,2,3,4-Tetrahydro-1-naphthylamine is also utilized in research and development for the exploration of new synthetic pathways and the creation of novel compounds with potential applications in various fields, including pharmaceuticals, materials science, and agrochemicals.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H13N/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-2,4,6,10H,3,5,7,11H2/p+1/t10-/m0/s1

Upstream product

• 86-57-7 1-Nitronaphthalene 
• 68253-36-1 1-tetralone oxime 
• 3349-64-2 1-tetralone oxime 
• 79817-66-6 1-nitro-1,2,3,4-tetrahydronaphthalene 
• 134-32-7 1-amino-naphthalene 
• 77287-34-4 formamide 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 
• 832684-26-1 (+/-)-1-azido-1,2,3,4-tetrahydronaphthalene 
• 3459-02-7 1,2,3,4-tetrahydro-1-naphthylamine hydrochloride 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 119-64-2 tetralin 
• 23357-52-0 (S)-1,2,3,4-tetrahydronapht-1-yl-amine 

Downstream Products

• 127761-16-4 chloro-acetic acid-(1,2,3,4-tetrahydro-[1]naphthylamide) 
• 58490-01-0 1-(4-Chloro-phenyl)-3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-urea 
• 58524-78-0 C₁₈H₂₀N₂O₃S 
• 63125-45-1 1-(4-Methoxy-phenyl)-3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-urea 
• 58490-15-6 1-Cyclohexyl-3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-urea 
• 58490-07-6 1-Benzyl-3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-urea 
• 59376-68-0 1-(4-Methoxy-benzyl)-3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-urea 
• 114352-02-2 (S)-1,2,3,4-tetrahydro-1-naphthylamine hydrogen D-tartrate 
• 79817-66-6 1-nitro-1,2,3,4-tetrahydronaphthalene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 129295-67-6 2-phenyl-N-(1,2,3,4-tetrahydro-naphthalen-1-yl)acetamide 
• 23357-52-0 (S)-1,2,3,4-tetrahydronapht-1-yl-amine 
• 23357-46-2 (R)-1,2,3,4-Tetrahydro-1-naphthylamine 
• 3349-64-2 1-tetralone oxime 

Relevant articles and documents

A novel chimeric amine dehydrogenase shows altered substrate specificity compared to its parent enzymes

We created a novel chimeric amine dehydrogenase (AmDH) via domain shuffling of two parent AmDHs ('L- and F-AmDH'), which in turn had been generated from leucine and phenylalanine DH, respectively. Unlike the parent proteins, the chimeric AmDH ('cFL-AmDH') catalyzes the amination of acetophenone to (R)-methylbenzylamine and adamantylmethylketone to adamantylethylamine.

Palladium/Lewis Acid Co-catalyzed Divergent Asymmetric Ring-Opening Reactions of Azabenzonorbornadienes with Alcohols

By fine tuning the combinations of chiral palladium catalysts and Lewis acids, both the additional and reductive asymmetric ring-opening reactions of azabenzonorbornadienes with alcohols were accomplished with good chemoselectivity, regioselectivity, and enantioselectivity. It was proven that the reductive ring-opening products were generated through a transfer-hydrogenation process with alcohols as hydrogen source.

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.

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.