5176-30-7

Basic information

• Product Name: 1,2,3,4-tetrahydro-naphthalen-1,4-imine
• Synonyms: 1,2,3,4-tetrahydro-naphthalen-1,4-imine;7-Aza-benzonobornene;Naphthalen-1,4-imine, 1,2,3,4-tetrahydro-;1,2,3,4-Tetrahydro-1,4-epiminonaphthalene;11-Azatricyclo[6.2.1.02,7]undeca-2,4,6-triene;7-Azabenzonorbornene;1,2,3,4-tetrahydro-naphthalen-1,4-imine-5;11-azatricyclo[6.2.1.0,]undeca-2,4,6-triene
• CAS NO: 5176-30-7
• Molecular Formula: C₁₀H₁₁N
• Molecular Weight: 145.2
• Mol File: 5176-30-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 157-161℃
• Boiling Point: 241℃
• Flash Point: 104℃
• Appearance: /
• Density: 1.107
• Vapor Pressure: 0.0368mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: 1,2,3,4-tetrahydro-naphthalen-1,4-imine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-tetrahydro-naphthalen-1,4-imine(5176-30-7)
• EPA Substance Registry System: 1,2,3,4-tetrahydro-naphthalen-1,4-imine(5176-30-7)

Safety Data

• Hazardous Substances Data: 5176-30-7(Hazardous Substances Data)

Usage

Description

1,2,3,4-tetrahydro-naphthalen-1,4-imine, also known as 4-tetralone imine, is a cyclic imine chemical compound that features a naphthalene ring with a nitrogen atom attached to one of the carbon atoms, creating a five-membered ring. This organic compound serves as a versatile building block in the synthesis of pharmaceuticals, dyes, polymers, and other industrial chemicals.

Uses

Used in Pharmaceutical Synthesis:
1,2,3,4-tetrahydro-naphthalen-1,4-imine is used as a key intermediate in the production of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Dye Production:
As a building block, 1,2,3,4-tetrahydro-naphthalen-1,4-imine is utilized in the synthesis of dyes, contributing to the color and properties of these compounds for use in various industries.
Used in Polymer Production:
1,2,3,4-tetrahydro-naphthalen-1,4-imine also plays a role in the creation of polymers, where its structural attributes can enhance the polymer's characteristics and performance in different applications.
Used in Industrial Chemicals:
1,2,3,4-tetrahydro-naphthalen-1,4-imine is employed as a component in the formulation of various industrial chemicals, broadening its range of applications across different sectors.
Safety Note:
Due to its toxic nature, 1,2,3,4-tetrahydro-naphthalen-1,4-imine requires careful handling to prevent skin, eye, and respiratory system irritation. Proper safety measures should be taken during its use and production.

InChI:InChI=1/C10H11N/c1-2-4-8-7(3-1)9-5-6-10(8)11-9/h1-4,9-11H,5-6H2

Upstream product

• 118-92-3 anthranilic acid 
• 5176-28-3 N-(tert-butoxycarbonyl)-1,4-dihydro-1,4-iminonaphthalene 
• 1072-85-1 o-fluorobromobenzene 
• 5176-32-9 tert-butyl 1,2,3,4-tetrahydro-1,4-epiminonaphthalene-9-carboxylate 
• 72590-96-6 9-chloro-1,2,3,4-tetrahydronaphthalen-1,4-imine 

Downstream Products

• 942491-77-2 2,2,2-trifluoro-1-(1,2,3,4-tetrahydro-1,4-epiminonaphth-9-yl)ethanone 
• 34353-23-6 N-benzoyl-7-azabenzobicyclo[2.2.1]heptadiene 
• 34353-25-8 N-benzoyl-7-azabenzobicyclo[2.2.1]heptene 

Relevant articles and documents

RESORCINOL DERIVATIVE AS HSP90 INHIBITOR

The present invention relates to a compound represented by formula (I) of a resorcinol derivative as an HSP90 inhibitor or pharmaceutically accepted salts thereof. The compound in the present invention has the activity of inhibiting heat shock protein HSP90. Therefore, the compound in the present invention is used to treat proliferative diseases such as cancer and neurodegenerative diseases. The present invention further provides the compounds and preparation methods for pharmaceutical compositions comprising the compounds, a method for treating diseases, and pharmaceutical compositions comprising the compounds.

Transnitrosation of thiols from aliphatic N-nitrosamines: S-nitrosation and indirect generation of nitric oxide

S-Nitrosothiols and heme nitrosyl species are nitric oxide (NO)-derived metabolites that provide an endogenous reservoir of NO and also play roles in protein S-nitrosation, that is, transnitrosation of thiols (or thiolates) in proteins, thereby regulating protein functions and signal transduction pathways. Intriguingly, endogenous N-nitrosamines are present in similar abundance to S-nitrosothiols, and though they are thought to play similar physiological roles to S-nitrosothiols, their transnitrosation reactivities and their contribution to biological events are little understood. Herein we report aliphatic N-nitroso derivatives of 7-azabicyclo[2.2.1]heptanes, which do not act as NO donors themselves, but can transnitrosate thiols. On the basis of the calculated activation energies of transnitrosation and the aorta smooth-muscle relaxation activities of these N-nitrosamines, we present a possible scenario of S-transnitrosation from aliphatic N-nitrosamines, leading to indirect generation of NO. Copyright

An Evaluation of Amide Group Planarity in 7-Azabicyclo[2.2.1]heptane Amides. Low Amide Bond Rotation Barrier in Solution

Here we show that amides of bicyclic 7-azabicyclo[2.2.1]heptane are intrinsically nitrogen-pyramidal. Single-crystal X-ray diffraction structures of some relevant bicyclic amides, including the prototype N-benzoyl-7-azabicyclo[2.2.1]heptane, exhibited nitrogen-pyramidalization in the solid state. We evaluated the rotational barriers about the amide bonds of various N-benzoyl-7-azabicyclo[2.2.1]heptanes in solution. The observed reduction of the rotational barriers of the bicyclic amides, as compared with those of the monocyclic pyrrolidine amides, is consistent with a nitrogen-pyramidal structure of 7-azabicyclo[2.2.1]heptane amides in solution. A good correlation was found between the magnitudes of the rotational barrier of N-benzoyl-7-azabicyclo[2.2.1]heptanes bearing para-substituents on the benzoyl group and the Hammett's σp+ constants, and this is consistent with the similarity of the solution structures. Calculations with the density functional theory reproduced the nitrogen-pyramidal structures of these bicyclic amides as energy minima. The calculated magnitudes of electron delocalization from the nitrogen nonbonding nN orbital to the carbonyl π* orbital of the amide group evaluated by application of the bond model theory correlated well with the rotational barriers of a variety of amides, including amides of 7-azabicyclo[2.2.1]heptane. The nonplanarity of the amide nitrogen of 7-azabicyclo[2.2.1]heptanes would be derived from nitrogen-pyramidalization due to the CNC angle strain and twisting of the amide bond due to the allylic strain.