371-40-4

Basic information

• Product Name: 4-Fluoroaniline
• Synonyms: 1,4-fluorobenzenamine;4-Fluoranilin;4-fluoranilin(czech);4-fluoro-anilin;4-fluoro-benzenamin;4-Fluoronaniline;Aniline, 4-fluoro-;Aniline, p-fluoro-
• CAS NO: 371-40-4
• Molecular Formula: C₆H₆FN
• Molecular Weight: 111.12
• EINECS: 206-735-5
• Product Categories: Fluoro-Aromatics;Anilines, Aromatic Amines and Nitro Compounds;Fluorobenzene;Amines;Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Fluorine series;amine | alkyl Fluorine;Amines, Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 371-40-4.mol

Chemical Properties

• Melting Point: -1.9 °C
• Boiling Point: 187 °C767 mm Hg(lit.)
• Flash Point: 165 °F
• Appearance: Clear pale yellow to red-brown/Oily Liquid
• Density: 1.173 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.04mmHg at 25°C
• Refractive Index: n20/D 1.539(lit.)
• Storage Temp.: 2-8°C
• Solubility: 33g/l
• PKA: 4.65(at 25℃)
• Water Solubility: 33 g/L (20 ºC)
• Stability: Stable. Incompatible with acids, oxidizing agents.
• Merck: 14,4169
• BRN: 742030
• CAS DataBase Reference: 4-Fluoroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluoroaniline(371-40-4)
• EPA Substance Registry System: 4-Fluoroaniline(371-40-4)

Safety Data

• 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
• RIDADR: UN 2941 6.1/PG 3
• WGK Germany: 1
• RTECS: BY1575000
• TSCA: T
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 371-40-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluoroaniline is used as an intermediate in the manufacture of pharmaceuticals, contributing to the development of various medications.
Used in Analytical Chemistry:
4-Fluoroaniline serves as an analytical reagent in the enzymic detection of glucose, playing a crucial role in the accurate measurement of blood sugar levels.
Used in Agriculture:
As an intermediate, 4-Fluoroaniline is utilized in the production of herbicides and plant growth regulators, helping to control weeds and promote plant growth in the agricultural sector.
Used in Environmental Research:
4-Fluoroaniline may be employed as one of the target pollutants during the investigation of biodegradability of fluorinated compounds under aerobic conditions, aiding in understanding the environmental impact of such compounds.
Used in Material Science:
4-Fluoroaniline is used for the synthesis of luminescent and cationic monocyclometalated gold(III) monoaryl complexes, which have potential applications in various material science and technology fields.
Used in Ezetimibe Degradation:
4-Fluoroaniline is a degradation product of Ezetimibe (E975000), a medication used to lower cholesterol levels. Understanding its formation and properties can contribute to the assessment of the drug's long-term effects and safety.

Preparation

The better process in the one-step process is the nitrobenzene method, which is obtained by deoxygenation, hydrogenation and fluorination. With PdCl2-V2O5 as the catalyst and carbon monoxide as the reducing agent, the reaction was carried out at 160°C for 3h, and the yield of 4-fluoroaniline could reach 90%, with another 10% of aniline as a by-product. With PtO2 as the catalyst, BF3-HF as the fluorinating agent and hydrogen as the reducing agent, the reaction was carried out at 42℃ for 12.5h, with 100% conversion and 95% yield.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 654, 1948 DOI: 10.1021/ja01182a065The Journal of Organic Chemistry, 26, p. 4014, 1961 DOI: 10.1021/jo01068a089

Hazard

Toxic material.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by ingestion. Mutation data reported. A severe skin and eye irritant. When heated to decomposition it emits very toxic fumes of NOx and F-.

InChI:InChI:1S/C6H6FN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2

Upstream product

• 352-33-0 1-Chloro-4-fluorobenzene 
• 456-22-4 4-Fluorobenzoic acid 
• 100-65-2 N-Phenylhydroxylamine 
• 98-95-3 nitrobenzene 
• 350-46-9 4-Fluoronitrobenzene 
• 363-02-0 4,4’-difluorobenzophenone oxime 
• 71-43-2 benzene 
• 462-06-6 fluorobenzene 
• 117872-31-8 (4-Fluoro-phenyl)-carbamic acid 2-piperidin-1-yl-ethyl ester; hydrochloride 
• 3296-02-4 p-azidofluorobenzene 
• 7647-01-0 hydrogenchloride 
• 7664-41-7 ammonia 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 53477-44-4 C₇H₈FN₃ 

Downstream Products

• 780-05-2 (Z)-4-((4-fluorophenyl)amino)-4-oxobut-2-enoic acid 
• 348-45-8 N-(4-fluorophenyl)benzo[d]thiazol-2-amine 
• 2369-32-6 6-methyl-N-(4-fluorophenyl)benzo[d]thiazol-2-amine 
• 494-26-8 2,5-bis-(4-fluoro-anilino)-[1,4]benzoquinone-bis-(4-fluoro-phenylimine) 
• 327-23-1 (6-bromo-benzothiazol-2-yl)-(4-fluoro-phenyl)-amine 
• 391-91-3 2-cyano-3-[1-(4-fluoro-phenyl)-pyrrol-2-yl]-acrylic acid methyl ester 
• 314-53-4 4,5,6,7-tetrachloro-2-(4-fluoro-phenyl)-isoindoline-1,3-dione 
• 1494-14-0 (2-methyl-6-oxo-6,7-dihydro-1H-purin-8-ylmercapto)-acetic acid-(4-fluoro-anilide) 
• 457-77-2 ethyl 4-fluorophenylcarbamate 
• 351-83-7 4'-fluoroacetanilide 
• 448-39-5 N-(4-fluoro-2-nitrophenyl)acetamide 
• 331-98-6 N-benzylidene-4-fluoroaniline 
• 366-75-6 N-(4-fluorophenyl)benzamide 
• 330-98-3 N-(4-fluorophenyl)-N'-phenyl-urea 

Related news

Determination of the second-order 1H NMR parameters for the aromatic protons in 4-Fluoroaniline (cas 371-40-4) and application to the analysis of the 1H NMR spectra for the aromatic protons in N4-(4′-fluorophenyl)succinamic acid and in N4-(4′-fluorophenyl)-3,3-difluorosuccinamic acid07/21/2019

Four studies of the 1H NMR spectrum for the aromatic protons of 4-fluoroaniline between 1958 and 1974 give three very different solutions to the second-order, AA′BB′X, spectrum. A re-evaluation of the second-order spectrum was done at 300 MHz. Simultaneous simulations of the 1H NMR spectrum an...detailed

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