438-32-4

Basic information

• Product Name: 4-Fluoro-1-naphthylamine
• Synonyms: 1-Amino-4-fluoronaphthalene;1-Naphthalenamine,4-fluoro-(9CI);4-fluoro-1-aminonaphthalene;1-Fluoro-4-aminonaphthalene;4-Fluoro-1-naphthylamine;4-amino-1-fluoronaphthalene;4-fluoronaphthalen-1-aMine
• CAS NO: 438-32-4
• Molecular Formula: C₁₀H₈FN
• Molecular Weight: 161.18
• EINECS: 1533716-785-6
• Mol File: 438-32-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 48 °C
• Boiling Point: 309.8 °C at 760 mmHg
• Flash Point: 153.2 °C
• Appearance: /
• Density: 1.239 g/cm³
• Vapor Pressure: 0.000626mmHg at 25°C
• Refractive Index: 1.665
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 3.20±0.10(Predicted)
• CAS DataBase Reference: 4-Fluoro-1-naphthylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluoro-1-naphthylamine(438-32-4)
• EPA Substance Registry System: 4-Fluoro-1-naphthylamine(438-32-4)

Safety Data

• Hazardous Substances Data: 438-32-4(Hazardous Substances Data)

Usage

General Description

4-Fluoro-1-naphthylamine is an organic chemical compound with the molecular formula C10H8FN. It is a derivative of 1-naphthylamine, which is used in the synthesis of various pharmaceuticals and dyes. 4-Fluoro-1-naphthylamine is commonly used as a building block in organic synthesis and medicinal chemistry. It is also known for its potential use as a reagent in chemical reactions and as a precursor for the preparation of other fluorinated organic compounds. The compound is a white to off-white solid and is typically handled and used in a controlled laboratory environment due to its potential toxicity and hazards.

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 
• 776-34-1 1-amino-4-nitronaphthalene 
• 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 

Downstream Products

• 315-53-7 4-fluoro-1-hydroxynaphthalene 
• 1543-63-1 N-(4-chloro-phenyl)-N'-(4-fluoro-[1]naphthyl)-urea 
• 390-70-5 (4-fluoro-[1]naphthyl)-m-tolyl-amine 
• 17318-09-1 1-iodo-4-fluoronaphthalene 
• 315-51-5 1-chloro-4-fluoro-naphthalene 
• 13772-59-3 3-bromo-1-fluoronaphthalene 
• 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 
• 163275-62-5 3,6-Difluorobenzo(h)quinoline 
• 186268-27-9 3-amino-6-fluorobenzo[h]quinoline 
• 186268-26-8 6-Fluoro-3-nitro-benzo[h]quinoline 
• 388-44-3 5-fluoro-7,10-dimethyl-benzo[c]acridine 

Relevant articles and documents

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.

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.

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.