59832-12-1

Usage

Nitro group

A functional group consisting of an oxygen atom double-bonded to a nitrogen atom (-NO2).

Methyl-substituted naphthalene ring

A naphthalene molecule (two fused benzene rings) with a methyl group (-CH3) attached to one of the carbon atoms.

Yellow to orange crystalline substance

The compound forms yellow to orange crystals, which is a characteristic of its solid state.

Reagent in organic synthesis

1-NITRO-1-METHYL-2-NAPHTYLETHENE is commonly used as a starting material or intermediate in various organic reactions.

Synthesis of pharmaceuticals and agrochemicals

The compound serves as a precursor or building block in the production of certain drugs and pesticides.

Organic light-emitting diodes and optoelectronic devices

Due to its unique electronic and optical properties, 1-NITRO-1-METHYL-2-NAPHTYLETHENE has potential applications in the development of devices such as OLEDs (organic light-emitting diodes) and other optoelectronic technologies.

InChI:InChI=1/C13H11NO2/c1-10(14(15)16)8-11-6-7-12-4-2-3-5-13(12)9-11/h2-9H,1H3/b10-8+

Upstream product

• 79-24-3 Nitroethane 
• 66-99-9 β-naphthaldehyde 

Downstream Products

• 1419606-20-4 4-methyl-5-(naphthalen-2-yl)-2-phenylthiazole 
• 18085-04-6 1-methyl-2-(2-naphthyl)-ethylamine hydrochloride 
• 18085-03-5 (±)-1-(2-naphthyl)propan-2-amine 

Relevant academic research and scientific papers

Synthesis of Benzo[4,5]imidazo[2,1-b]thiazole by Copper(II)-Catalyzed Thioamination of Nitroalkene with 1H-Benzo[d]imidazole-2-thiol

A Copper(II)-catalyzed thioamination of β-nitroalkene with 1H-benzo[d]imidazole-2-thiol has been developed for the synthesis of benzo[4,5]imidazo[2,1-b]thiazole derivatives. A variety of N-fused benzoimidazothiazole derivatives are obtained in high yields through successive C?N and C?S bond formations. This protocol is also applicable to β-substituted β-nitroalkenes to afford 2,3-disubstituted benzoimidazothiazoles. (Figure presented.).

Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors

A series of naphthylisopropylamine and N-benzyl-4-methylthioamphetamine derivatives were evaluated as monoamine oxidase inhibitors. Their potencies were compared with those of a series of amphetamine derivatives, to test if the increase of electron richness of the aromatic ring and overall size of the molecule might improve their potency as enzyme inhibitors. Molecular dockings were performed to gain insight regarding the binding mode of these inhibitors and rationalize their different potencies. In the case of naphthylisopropylamine derivatives, the increased electron-donating capacity and size of the aromatic moiety resulting from replacement of the phenyl ring of amphetamine derivatives by a naphthalene system resulted in more potent compounds. In the other case, extension of the arylisopropylamine molecule by N-benzylation of the amino group led to a decrease in potency as monoamine oxidase inhibitors.

Development of a rationally designed, low abuse potential, biogenic amine releaser that suppresses cocaine self-administration

Convergent lines of evidence support a dual deficit model of stimulant withdrawal, where reductions in synaptic dopamine (DA) and 5-hydroxytryptamine (serotonin) (5-HT) contribute to dysphoria, drug craving, and relapse. Thus, we predicted that a nonamphetamine compound with substrate activity at DA and 5-HT transporters (i.e., a dual DA/5-HT releaser) would be an effective medication for treating stimulant addictions. Ideally, this type of medication would alleviate withdrawal symptoms, suppress cocaine self-administration, and lack side effects commonly associated with central nervous system stimulants. In the present work, more than 350 compounds were screened in vitro for activity as substrate-type releasing agents at DA, 5-HT, and norepinephrine transporters. These efforts identified PAL-287 (1-napthyl-2-aminopropane) as a nonamphetamine compound with potent substrate activity at biogenic amine transporters. In vivo microdialysis in rats demonstrated that PAL-287 (1-3 mg/kg i.v.) increased extracellular DA and 5-HT in frontal cortex, but effects on 5-HT were somewhat greater. PAL-287 induced substantially less locomotor stimulation than (+)-amphetamine, a drug that increases only extracellular DA. Administration of high-dose (+)-methamphetamine or (±)-3,4-methylenedioxymethamphetamine to rats produced long-lasting depletion of cortical 5-HT, whereas PAL-287 (18 mg/kg i.p. × 3) did not. PAL-287 displayed little or no reinforcing properties in rhesus monkeys trained to self-administer cocaine, yet PAL-287 produced a dose-dependent decrease in responding for cocaine when infused at a dose of 1.0 mg/kg/h. Collectively, the findings reported here demonstrate that nonamphetamine monoamine releasing agents such as PAL-287 might be promising candidate medications for the treatment of stimulant dependence.

Porphyrin synthesis from nitrocompounds

A new porphyrin synthesis starting from nitroalkenes or their equivalents is described. For example, octaethylporphyrin, coproporphyrin, porphyrin-1,2,3,4,5,6,7,8 octapropionic acid, and 2,7,12,17 tetraarylporphyrin are prepared in good yield from readily available materials such as 1-nitropropane, nitroethane, nitromethane, and aldehydes.

Cycloaddition of Isocyanides with 1-Aryl-2-nitro-1-propenes, Methyl 2-Nitro-3-arylpropenoates, and Methyl 2-Nitro-2,4-pentadienoates. Synthesis of 1-Hydroxyindoles and 1-Hydroxypyrroles

The cycloadditions of isocyanides with various aryl nitroalkenes have been investigated.When the aryl groups were XC6H4, naphthyl, and 2-pyridinyl, the reactions gave the 1-hydroxyindoles, 1-hydroxybenzoindoles, and 1-hydroxy-7-azaindole.When the ar