438-32-4

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluoro-1-naphthylamine is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with specific therapeutic properties. Its unique chemical structure allows for the creation of molecules with potential applications in treating a range of medical conditions.
Used in Dye Industry:
In the dye industry, 4-Fluoro-1-naphthylamine is used as a precursor for the preparation of dyes with specific color characteristics and properties. The incorporation of a fluorine atom can influence the dye's stability, solubility, and other functional attributes, making it suitable for various applications such as textiles, printing inks, and pigments.
Used in Organic Synthesis:
4-Fluoro-1-naphthylamine is utilized as a building block in organic synthesis, where it serves as a starting material for the creation of more complex organic compounds. Its reactivity and structural features make it a valuable component in the synthesis of a wide array of organic molecules.
Used in Medicinal Chemistry:
In medicinal chemistry, 4-Fluoro-1-naphthylamine is employed as a structural component in the design and synthesis of new drug candidates. Its presence can influence the pharmacokinetics, pharmacodynamics, and overall efficacy of the resulting compounds, contributing to the advancement of novel therapeutic agents.
Used in Chemical Reactions as a Reagent:
4-Fluoro-1-naphthylamine is used as a reagent in various chemical reactions, where it can participate in a range of processes such as substitution, addition, and condensation reactions. Its reactivity is valuable for the synthesis of new compounds and the modification of existing ones.
Used in the Preparation of Fluorinated Organic Compounds:
As a precursor, 4-Fluoro-1-naphthylamine is instrumental in the preparation of other fluorinated organic compounds. The introduction of fluorine can significantly alter the properties of organic molecules, making them more valuable for applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

InChI:InChI=1/C10H8FN/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H,12H2

Upstream product

• 341-92-4 1-fluoro-4-nitronaphthalene 
• 317-04-4 N-(4-fluoro-[1]naphthyl)-acetamide 
• 7647-01-0 hydrogenchloride 
• 7664-93-9 sulfuric acid 
• 321-38-0 1-Fluoronaphthalene 
• 573-03-5 4-fluoro-1-naphthoic acid 
• 17318-06-8 (4-fluoronaphthalen-1-yl)magnesium bromide 
• 341-41-3 1-bromo-4-fluoronaphthalene 
• 776-37-4 N-formyl-4-fluoro-1-naphthylamine 
• 776-34-1 1-amino-4-nitronaphthalene 

Downstream Products

• 1543-63-1 N-(4-chloro-phenyl)-N'-(4-fluoro-[1]naphthyl)-urea 
• 390-71-6 (4-fluoro-[1]naphthyl)-p-tolyl-amine 
• 13791-07-6 4-fluoro-N,N-dimethylnaphthalen-1-amine 
• 163275-59-0 6-Fluorobenzo[h]quinoline 
• 669-22-7 N,N'-bis-(4-fluoro-[1]naphthyl)-thiourea 
• 1572936-70-9 2-(4-fluoronaphthalen-1-ylamino)-5-nitrobenzoic acid 
• 2059-29-2 6-fluorobenzo[cd]indol-2(1H)-one 
• 1572936-63-0 2-(4-fluoronaphthalen-1-ylamino)-4-nitrobenzoic acid 
• 13772-61-7 1-fluoro-3-naphthoic acid 
• 13772-60-6 3-Cyano-1-fluor-naphthalin 
• 388-44-3 5-fluoro-7,10-dimethyl-benzo[c]acridine 
• 186268-26-8 6-Fluoro-3-nitro-benzo[h]quinoline 
• 186268-27-9 3-amino-6-fluorobenzo[h]quinoline 
• 163275-62-5 3,6-Difluorobenzo(h)quinoline 

Relevant academic research and scientific papers

Cobalt-Catalyzed Direct Carbonylative Synthesis of Free (NH)-Benzo[ cd]indol-2(1 H)-ones from Naphthylamides

A cobalt-catalyzed C-H carbonylation of naphthylamides for the synthesis of benzo[cd]indol-2(1H)-one scaffolds has been developed. The reaction employs a traceless directing group and uses benzene-1,3,5-triyl triormate as the CO source, affording various free (NH)-benzo[cd]indol-2(1H)-ones in moderate to high yields (up to 88%). Using this protocol, the total synthesis of BET bromodomain inhibitors A and B was accomplished as well.

AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS

In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.

Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds

Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C-C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (-NH2) and hydroxyl (-OH) groups to arylmetals in a scalable and environmentally friendly fashion remains a formidable synthetic challenge because of the absence of suitable heteroatom-transfer reagents. Here, we demonstrate the use of bench-stable N-H and N-alkyl oxaziridines derived from readily available terpenoid scaffolds as efficient multifunctional reagents for the direct primary amination and hydroxylation of structurally diverse aryl- and heteroarylmetals. This practical and scalable method provides one-step synthetic access to primary anilines and phenols at low temperature and avoids the use of transition-metal catalysts, ligands and additives, nitrogen-protecting groups, excess reagents and harsh workup conditions.

Non-deprotonative primary and secondary amination of (hetero)arylmetals

Herein we disclose a novel method for the facile transfer of primary (-NH2) and secondary amino groups (-NHR) to heteroaryl-as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or Erecting groups. This one-pot transformation allows unprecedented functional group tolerance and it is wellsuited for the amination of electron-rich, electron-deficient as well as structurally complex (hetero)arylmetals. In some of the cases, only catalytic amounts of a copper (l) salt is required.

Monna, a potent and selective blocker for transmembrane protein with unknown function 16/anoctamin-1

Transmembrane protein with unknown function 16/anoctamin-1 (ANO1) is a protein widely expressed in mammalian tissues, and it has the properties of the classic calcium-activated chloride channel (CaCC). This protein has been implicated in numerous major physiological functions. However, the lack of effective and selective blockers has hindered a detailed study of the physiological functions of this channel. In this study, we have developed a potent and selective blocker for endogenous ANO1 in Xenopus laevis oocytes (xANO1) using a drug screening method we previously established (Oh et al., 2008). We have synthesized a number of anthranilic acid derivatives and have determined the correlation between biological activity and the nature and position of substituents in these derived compounds. A structure-activity relationship revealed novel chemical classes of xANO1 blockers. The derivatives contain a-NO2 group on position 5 of a naphthyl group-substituted anthranilic acid, and they fully blocked xANO1 chloride currents with an IC 5050 of 0.08 μM for xANO1. Selectivity tests revealed that other chloride channels such as bestrophin-1, chloride channel protein 2, and cystic fibrosis transmembrane conductance regulator were not appreciably blocked by 10～30 μM MONNA. The potent and selective blockers for ANO1 identified here should permit pharmacological dissection of ANO1/CaCC function and serve as potential candidates for drug therapy of related diseases such as hypertension, cystic fibrosis, bronchitis, asthma, and hyperalgesia.

NH+ - F hydrogen bonding in a fluorinated "Proton Sponge" derivative: Integration of solution, solid-state, gas-phase, and computational studies

We report detailed studies on the characterization of an intramolecular NH - F hydrogen bond formed within a fluorinated "proton sponge" derivative. An ammonium ion, generated from 8-fluoro-N,N-dimethylnaphthalen-1- amine, serves as a charged hydrogen bond donor to a covalently bound fluorine appropriately positioned on the naphthalene skeleton. Potentiometric titrations of various N,N-dimethylnaphthalen-1-amines demonstrate a significant increase in basicity when hydrogen bonding is possible. X-ray crystallography reveals that NH - F hydrogen bonding in protonated 8-fluoro-N,N-di-methylnaphthalen-1-amine is heavily influenced by ion pairing in the solid state; bifurcated and trifurcated hydrogen bonds are formed depending on the counterion utilized. Compelling evidence of hydrogen bonding in the 8-fluoro-N,N-dimethylnaphthyl-1- ammonium cation is provided by gas-phase cryogenic vibrational photodissociation spectroscopy. Solution-phase infrared spectroscopy provides complementary results, and the frequencies of the N - H stretching mode in both phases are in excellent agreement with the computed vibrational spectra. NMR analysis of protonated 8-fluoro-N,N-dimethylnaphthalen-1-amine demonstrates significant H - F coupling between the N - H hydrogen and fluorine that cannot be attributed to long-range, through-bond interactions; the couplings correlate favorably with calculated values. The results obtained from these experiments are congruent with the formation of an NH - F hydrogen bond upon protonation of 8-fluoro-N,N-dimethylnaphthalen-1-amine.

SUBSTITUTED GUANIDINES AND DERIVATIVES THEREOF AS MODULATORS OF NEUROTRANSMITTER RELEASE AND NOVEL METHODOLOGY FOR IDENTIFYING NEUROTRANSMITTER RELEASE BLOCKERS

Modulators of neurotransmitter release including substituted guanidines, N"-aminoguanidines, and N,N'N",N"'-tetrasubstituted hydrazinedicarboximidamides, and pharmaceutical compositions thereof are disclosed. Also disclosed are methods involving the use of such neurotransmitter release modulators for the treatment or prevention of pathophysiologic conditions characterized by the release of excessive or inappropriate levels of neurotransmitters. Also disclosed are screening assays for compounds which selectively inhibit glutamate release. Also disclosed are methods of blocking voltage sensitive sodium and calcium channels in mammalian nerve cells. "

Substituted naphthyl anthranilic acids

This invention relates to novel N-(substituted-naphthyl-1)anthranilic acids and their salts, and also to a process for the synthesis of these compounds. These compounds and their pharmaceutically acceptable salts are novel and therapeutically useful as anti-inflammatory agents and analgesics, and they may be orally or non-orally applied, or administered by other methods.