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

Description

4-Fluoro-1-naphthylamine is an organic chemical compound characterized by the molecular formula C10H8FN. It is a derivative of 1-naphthylamine, distinguished by the presence of a fluorine atom at the 4-position. 4-Fluoro-1-naphthylamine is utilized in the synthesis of pharmaceuticals and dyes, and is recognized for its role as a building block in organic synthesis and medicinal chemistry. Additionally, it is known for its potential as a reagent in chemical reactions and as a precursor for the preparation of other fluorinated organic compounds. 4-Fluoro-1-naphthylamine is a white to off-white solid, and due to its potential toxicity and hazards, it is typically handled and used in a controlled laboratory environment.

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

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

Downstream Products

• 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 
• 13791-07-6 4-fluoro-N,N-dimethylnaphthalen-1-amine 
• 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 
• 669-22-7 N,N'-bis-(4-fluoro-[1]naphthyl)-thiourea 
• 163275-59-0 6-Fluorobenzo[h]quinoline 
• 390-71-6 (4-fluoro-[1]naphthyl)-p-tolyl-amine 

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.

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.