32666-56-1

Basic information

• Product Name: 1-Naphthalenamine,5,8-dihydro-
• Synonyms: 1-Naphthalenamine,5,8-dihydro-;5,8-Dihydro-1-naphthalenamine;5,8-dihydronaphthalen-1-amine
• CAS NO: 32666-56-1
• Molecular Formula: C₁₀H₁₁N
• Molecular Weight: 145.2
• Mol File: 32666-56-1.mol

Chemical Properties

• Melting Point: 37.5°C
• Boiling Point: 254.33°C (rough estimate)
• Flash Point: 135.2 °C
• Appearance: /
• Density: 1.0353 (rough estimate)
• Refractive Index: 1.5000 (estimate)
• CAS DataBase Reference: 1-Naphthalenamine,5,8-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthalenamine,5,8-dihydro-(32666-56-1)
• EPA Substance Registry System: 1-Naphthalenamine,5,8-dihydro-(32666-56-1)

Safety Data

• Hazardous Substances Data: 32666-56-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1-Naphthalenamine,5,8-dihydrois used as a chemical intermediate for the synthesis of various complex organic compounds. Its unique structure allows for further functionalization and modification, making it a valuable building block in the development of new molecules with potential applications in various industries.
Used in Pharmaceutical Research:
1-Naphthalenamine,5,8-dihydrois used as a research compound in the field of pharmaceuticals. Its amine functionality and naphthalene backbone provide a foundation for the design and synthesis of new drug candidates, particularly those targeting specific biological receptors or enzymes. 1-Naphthalenamine,5,8-dihydro-'s reactivity and stability are crucial factors in determining its suitability for medicinal applications.
Used in Dye and Pigment Production:
1-Naphthalenamine,5,8-dihydrois used as a precursor in the production of dyes and pigments. Its chemical structure can be modified to create a range of colors, making it a versatile component in the formulation of various colorants used in industries such as textiles, plastics, and printing inks.
Used in Material Science:
1-Naphthalenamine,5,8-dihydrois used as a component in the development of advanced materials with specific properties. Its incorporation into polymers or other materials can impart unique characteristics, such as improved conductivity, enhanced stability, or tailored reactivity, which can be exploited in various applications, including electronics, sensors, and energy storage devices.

Upstream product

• 134-32-7 1-amino-naphthalene 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 108-88-3 toluene 
• 67-56-1 methanol 
• 7664-41-7 ammonia 

Downstream Products

• 27673-48-9 5,8-dihydro-1-naphthol 
• 612-17-9 1,4-dihydronaphthalene 
• 20191-76-8 2,4-dibromo-1-naphthylamine 
• 2217-41-6 1-amino-5,6,7,8-tetrahydronaphthalene 
• 130-15-4 [1,4]naphthoquinone 
• 144-62-7 oxalic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 76149-15-0 4-<2-(N,N-di-n-propylamino)ethyl>indole 
• 91374-21-9 Ropinirole 
• 529-35-1 5,6,7,8-Tetrahydronaphthalen-1-ol 
• 7499-73-2 N-(4-bromo-2-nitronaphthalen-1-yl)acetamide 

Relevant articles and documents

COMPOUND SUITABLE FOR DETECTION OF VESICULAR ACETYLCHOLINE TRANSPORTER

PROBLEM TO BE SOLVED: To provide a compound suitable for detection of vesicular acetylcholine transporter which can be also used as a compound labeled in PET method. SOLUTION: The present invention provides a compound represented by formula (I), where Rs

Suitable for vesicle acetylecholine translocator detection compound (by machine translation)

The present invention provides a compound represented by formula (I), wherein in formula (I), R 1 represents CH 3 , F, (CH 2 ) n -F, NH-(CH 2 ) n -F, O-(CH 2 ) n -F or S-(CH 2 ) n -F, and n represents an integer of 1 to 3.

The development of a short route to the API ropinirole hydrochloride

A four-step, three-stage synthesis of the API ropinirole hydrochloride has been developed from a commercially available naphthalene derivative. The new route has half the step-count and twice the overall yield of the current manufacturing process. Key features of the synthesis are a regioselective Birch reduction and an ozonolysis with concomitant ring closure to induce the required ring contraction.

New systematically modified vesamicol analogs and their affinity and selectivity for the vesicular acetylcholine transporter - A critical examination of the lead structure

To verify vesamicol as lead structure in the development of radioligands for imaging of VAChT in the brain by PET, we systematically modified this molecule and investigated four different groups of derivatives. Structural changes were conducted in all three ring systems A, B, and C resulting in a library of different vesamicol analogs. Based on their in vitro binding affinity toward VAChT as well as σ1 and σ2 receptors, we performed a structure-affinity relationship (SAR) study regarding both affinity and selectivity. The compounds possessed VAChT affinities in the range of 1.32 nM (benzovesamicol) to >10 mM and selectivity factors from 0.1 to 73 regarding σ1 and σ2 receptors, respectively. We could confirm the exceptional position of benzovesamicols as most affine VAChT ligands. However, we also observed that most of the compounds with high VAChT affinity demonstrated considerable affinity in particular to the σ1 receptor. Finally, none of the various vesamicol analogs in all four groups showed an in vitro binding profile suitable for specific VAChT imaging in the brain.

Reduction of polycyclic aromatic hydrocarbons promoted by cobalt or manganese nanoparticles

A new methodology for the partial reduction of polycyclic aromatic and heteroaromatic hydrocarbons under mild reaction conditions is presented, the process being a reasonable alternative to the catalytic hydrogenation or the Birch reaction. The reduction protocol described is based on the use of cobalt or manganese nanoparticles generated in situ in a simple and economic way, by reduction of commercially available CoCl2·6H2O or MnCl2·2H2O in the presence of lithium sand and the corresponding PAH, acting itself as an electron carrier. The use of a deuterium-oxide-containing cobalt(II) salt allows the simple preparation of deuterium labeled products. The regiochemistry and degree of reduction in the case of 1-substituted naphthalene derivatives markedly depends on the nature of the metal-NPs used.

Radioiodinated benzovesamicol analogs for cholinergic nerve mapping

Radioiodinated benzovesamicol analogs which selectively localize in presynaptic cholinergic neurons of the general formula: STR1 where X is selected from the group consisting of H, OH, NH2, NHCO-3-[I]-Ph, and a radioactive isotope of iodine, and Y is selected from the group of H and a radioactive isotope of iodine, Y being H is X contains iodine. Illustrative examples include: (±)-trans-2-hydroxy-5-iodo-3-(4-phenylpiperidino)tetralin; (±)-trans-3-hydroxy-5-iodo-2-(4-phenylpiperidino)tetralin; (±)-trans-5-amino-2-hydroxy-8-iodo-3-(4-phenylpiperidino)tetralin; and (±)-trans-2-hydroxy-5-(3-iodobenzamido)-3-(4-phenylpiperidino)tetralin. The novel radioiodinated benzovesamicol analogs may be used as radiopharmaceuticals to visualize cholinergic neurons with conventional imaging devices which are typically found in most nuclear medicine or radiology clinics.

Synthesis, in Vitro Acetylcholine-Storage-Blocking Activities, and Biological Properties of Derivatives and Analogues of trans-2-(4-Phenylpiperidino)cyclohexanol (Vesamicol)

Eighty-four analogues and derivatives of the acetylcholine-storage-blocking drug trans-2-(4-phenylpiperidino)cyclohexanol (vesamicol) were synthesized, and their potencies were evaluated with the acetylcholine active-transport assay utilizing purified synaptic vesicles from Torpedo electric organ.The parent drug exhibits enantioselectivity, with (-)-vesamicol being 25-fold more potent than (+)-vesamicol.The atomic structure and absolute configuration of (+)-vesamicol were determined by X-ray crystallography.The absolute configuration of (-)-vesamicol is 1R,2R.Structure-activity evidence indicates that (-)-vesamicol does not act as an acetylcholine analogue.Alterations to all three rings can have large effects on potency.Unexpectedly, analogues locking the alcohol and ammonium groups trans-diequatorial or trans-diaxial both exhibit good potency.A potent benzovesamicol family has been discovered that is suitable for facile elaboration of the sort useful in affinity labeling and affinity chromatography applications.A good correlation was found between potencies as assessed by the acetylcholine transport assay and LD50 values in mouse.