4-Fluoroaniline

Base Information

• Chemical Name: 4-Fluoroaniline
• CAS No.: 371-40-4
• Molecular Formula: C6H6FN
• Molecular Weight: 111.119
• Hs Code.: 2921.42
• European Community (EC) Number: 206-735-5
• NSC Number: 579
• UN Number: 2941
• UNII: 60HI1G076Z
• DSSTox Substance ID: DTXSID9022027
• Nikkaji Number: J33.843E
• Wikidata: Q27103764
• Metabolomics Workbench ID: 51758
• ChEMBL ID: CHEMBL32014
• Mol file: 371-40-4.mol

Synonyms:benzenamine, 4-fluoro-;Aniline, 4-fluoro-;Aniline, p-fluoro- (8CI);4-Fluoranilin;4-Fluorobenzenamine;4-12-00-01104 (Beilstein Handbook Reference);p-Fluorophenylamine;1-Amino-4-fluorobenzene;4-Fluoranilin [Czech];Aniline, p-fluoro-;para-Fluoroaniline;p-fluoroaniline;

Chemical Property of 4-Fluoroaniline

Chemical Property:

• Appearance/Colour: light yellow to gold-coloured liquid
• Vapor Pressure: 4.04mmHg at 25°C
• Melting Point: -1.9 °C
• Refractive Index: 1.5400
• Boiling Point: 188.9 °C at 760 mmHg
• PKA: 4.65(at 25℃)
• Flash Point: 77.9 °C
• PSA: 26.02000
• Density: 1.158 g/cm³
• LogP: 1.98910
• Storage Temp.: 2-8°C
• Solubility.: 33g/l
• Water Solubility.: 33 g/L (20 ºC)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 111.048427358
• Heavy Atom Count: 8
• Complexity: 66.9
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

4-Fluoroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi, C, T
• Hazard Codes: C,T,Xi,Xn
• Statements: 22-34-36/38-33-23/24/25
• Safety Statements: 26-36/37/39-45-37/39-28

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: C1=CC(=CC=C1N)F
• Uses: 4-Fluoroaniline is a degradation product of Ezetimibe (E975000). 4-Fluoroaniline is used as an analytical reagent in the enzymic detection of glucose. Intermediate in the manufacture of herbicides and plant growth regulators. 4-Fluoroaniline may be employed as one of the target pollutant during the investigation of biodegradability of fluorinated compounds under aerobic conditions. It may be used for the synthesis of luminescent and cationic monocyclometalated gold(III) monoaryl complexes.

Technology Process of 4-Fluoroaniline

There total 109 articles about 4-Fluoroaniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

bis-(4-fluorophenyl)diazene (332-07-0,51788-93-3,51789-00-5) → 4-fluoroaniline (371-40-4)

Guidance literature:

With lithium aluminium tetrahydride; titanium tetrachloride; In diethyl ether; at 20 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.07.089

Reference yield: 97.0%

p-azidofluorobenzene (3296-02-4) → 4-fluoroaniline (371-40-4)

Guidance literature:

With D-glucose; potassium hydroxide; In water; N,N-dimethyl-formamide; at 85 ℃; for 0.3h; chemoselective reaction; Green chemistry;

DOI:10.1039/c7gc01593c

Reference yield: 95.0%

1-Chloro-4-fluorobenzene (352-33-0) → 4-fluoroaniline (371-40-4)

Guidance literature:

With copper(ll) sulfate pentahydrate; ammonium hydroxide; In PEG₁₀₀₀-DIL; methyl cyclohexane; at 60 ℃; for 5h;

DOI:10.1002/jccs.201000084

upstream raw materials:

1-Chloro-4-fluorobenzene

4-Fluorobenzoic acid

N-Phenylhydroxylamine

nitrobenzene

Downstream raw materials:

(Z)-4-((4-fluorophenyl)amino)-4-oxobut-2-enoic acid

N-(4-fluorophenyl)benzo[d]thiazol-2-amine

6-methyl-N-(4-fluorophenyl)benzo[d]thiazol-2-amine

2,5-bis-(4-fluoro-anilino)-[1,4]benzoquinone-bis-(4-fluoro-phenylimine)

Refernces

Tris(pentafluorophenyl)borane-catalyzed three-component reaction for the synthesis of 1,8-dioxodecahydroacridines under solvent-free conditions

10.1055/s-2008-1067039

The study presents a mild and efficient method for synthesizing 1,8-dioxodecahydroacridines via a three-component reaction involving a 1,3-dione, an aldehyde, and an amine, catalyzed by tris(pentafluorophenyl)borane [B(C6F5)3] under solvent-free conditions. The chemicals involved include 1,3-cyclohexanedione as the 1,3-dione, various aldehydes (such as benzaldehyde, aliphatic aldehydes, and heteroaromatic aldehydes), and different amines (like aniline and 4-fluoroaniline). The role of B(C6F5)3 is to act as a Lewis acid catalyst, facilitating the reaction to proceed at room temperature with high yields of the desired 1,8-dioxodecahydroacridines. The study highlights the advantages of this method over traditional Hantzsch reactions, such as shorter reaction times, milder conditions, and higher yields, making it a significant advancement in the synthesis of this class of compounds, which have applications in pharmaceuticals, dyes, and materials science.

Synthesis and cytotoxicity studies of quinoline-3-carbonitrile derivatives

10.1016/j.cclet.2010.03.016

The study focuses on the design, synthesis, and in vitro cytotoxicity evaluation of a series of quinoline-3-carbonitrile derivatives against four cancer cell lines: A549 (lung), HT-29 (colon), MDA-MB-231 (breast), and SMMC-7721 (liver). The research aimed to develop potent and selective anti-tumor agents by replacing the quinazoline scaffold of Gefitinib, an EGFR tyrosine kinase inhibitor, with a quinoline-3-carbonitrile scaffold. The synthesized compounds were tested for their cytotoxic effects using the MTT assay, and the results showed that several of these derivatives exhibited superior selective cytotoxicity against the SMMC-7721 cell line compared to Gefitinib, with compound 11g being the most potent among them. The study also provided preliminary insights into the structure-activity relationships of these compounds, suggesting their potential as anti-cancer agents. Further research on their anti-tumor activities and detailed structure-activity relationships is ongoing.