350-46-9

Basic information

• Product Name: 4-Fluoronitrobenzene
• Synonyms: 4-Fluornitrobenzol;4-fluoro-1-nitrobenzene;Benzene,1-fluoro-4-nitro-;Fluoronitrobenzene3;Fluoronitrobenzenecolorlesssolid;4-Fluoronitrobenzene p-Fluoronitrobenzene;1-Fluoro-4-Nitrobenzene(4-Fluoronitrobenzene;p-Fluoronitrobenzene,99%
• CAS NO: 350-46-9
• Molecular Formula: C₆H₄FNO₂
• Molecular Weight: 141.1
• EINECS: 206-502-8
• Product Categories: Aromatic Halides (substituted);Halides;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 350-46-9.mol
• Article Data: 162

Chemical Properties

• Melting Point: 21 °C(lit.)
• Boiling Point: 205 °C(lit.)
• Flash Point: 182 °F
• Appearance: deep greenish-yellow/Liquid After Melting
• Density: 1.33 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: 5.5 mm Hg ( 70 °C)
• Refractive Index: n20/D 1.531(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: Insoluble in water.
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 606923
• CAS DataBase Reference: 4-Fluoronitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluoronitrobenzene(350-46-9)
• EPA Substance Registry System: 4-Fluoronitrobenzene(350-46-9)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 20/21/22-33
• Safety Statements: 36-36/37
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 1
• RTECS: DA1400000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 350-46-9(Hazardous Substances Data)

Usage

Description

4-Fluoronitrobenzene, also known as 4-Nitrofluorobenzene, is an aryl fluorinated building block and a common intermediate used for the synthesis of various industrially useful compounds. It is characterized by its yellow liquid appearance and plays a significant role in the production of novel soluble aromatic polyimides, such as 1,3,5-Tris(4-aminophenoxy)benzene (TAB).

Uses

Used in Chemical Synthesis:
4-Fluoronitrobenzene is used as a key intermediate in the chemical synthesis industry for the production of a wide range of compounds. Its unique structure allows for versatile reactions and the creation of various derivatives, making it a valuable component in the synthesis of pharmaceuticals, dyes, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Fluoronitrobenzene is utilized as a pharmaceutical intermediate. Its properties enable the development of new drugs with potential therapeutic applications, contributing to the advancement of medical treatments.
Used in Hair Dye Industry:
4-Fluoronitrobenzene is also used as a component in the hair dye industry. Its incorporation into hair dye formulations can enhance the color properties and improve the overall performance of the product, providing consumers with better hair coloring experiences.
Used in Polymer Industry:
In the polymer industry, 4-Fluoronitrobenzene is used for the preparation of novel soluble aromatic polyimides, such as 1,3,5-Tris(4-aminophenoxy)benzene (TAB). These polyimides exhibit unique properties, such as high thermal stability and excellent mechanical strength, making them suitable for various applications, including aerospace, electronics, and automotive industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 6034, 1956 DOI: 10.1021/ja01604a022Tetrahedron, 52, p. 23, 1996 DOI: 10.1016/0040-4020(95)00867-8Tetrahedron Letters, 30, p. 7199, 1989 DOI: 10.1016/S0040-4039(01)93933-4

Flammability and Explosibility

Nonflammable

Purification Methods

Crystallise it from EtOH. [Beilstein 5 H 241, 5 IV 719.]

InChI:InChI=1/C6H4FNO2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H

Upstream product

• 462-06-6 fluorobenzene 
• 591-09-3 nitro acetate 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 100-01-6 4-nitro-aniline 
• 100-00-5 4-chlorobenzonitrile 
• 99-65-0 meta-dinitrobenzene 
• 34467-53-3 p-fluoronitrobenzene anion 
• 598-58-3 methyl nitrate 
• 121-73-3 3-Nitrochlorobenzene 
• 355-02-2 perfluoro(methylcyclohexane) 
• 54480-44-3 N,N-dimethyl-N'-(4-methoxyphenyl)-1,4-phenylendiamine 
• 123199-74-6 C₉F₂₄P^(1-)*C₆H₄N₃O₂⁽¹⁺⁾ 
• 13118-32-6 p-nitrophenyldimethylsulphonium methylsulphate 
• 29843-53-6 dimethyl(p-nitrophenyl)sulfonium perchlorate 

Downstream Products

• 6574-15-8 1-(4-nitrophenyl)piperidine 
• 351-83-7 4'-fluoroacetanilide 
• 16078-86-7 4-Hydroxy-4'-nitrodiphenylamine 
• 13663-59-7 N-(4-nitrophenyl)cyclohexylamine 
• 620-89-3 4-methyl-N-(4-nitrophenyl)aniline 
• 16124-69-9 4-[(4-nitrophenyl)amino]benzoic acid 
• 3665-80-3 N-Ethyl-4-nitroanilin 
• 1965-54-4 N-(2-hydroxyethyl)-4-nitroaniline 
• 16365-27-8 2-(4-nitrophenoxy)ethanol 
• 1836-74-4 4-(4-chlorophenoxy)nitrobenzene 
• 85951-93-5 (3,5-dimethyl-phenyl)-(4-nitro-phenyl)-amine 
• 5431-36-7 NSC 13585 
• 2216-15-1 1-diethylamino-4-nitrobenzene 
• 58259-34-0 N-butyl-4-nitroaniline 

Relevant articles and documents

Method for synthesizing nitro (hetero) aromatic hydrocarbon

The invention discloses a method for synthesizing nitro (hetero) aromatic hydrocarbon, and belongs to the field of organic synthesis. According to the method, simple (hetero) aromatic hydrocarbon is taken as an initial raw material and is stirred and reacted in an organic solvent at 40-100 DEG C under the action of a nitration reagent, a lewis acid catalyst and protective gas, and nitro (hetero) aromatic hydrocarbon can be obtained. The method provided by the invention has the advantages of cheap and easily available raw materials, mild reaction conditions, simple preparation process, good chemical selectivity, wide substrate application range, easy amplification and the like, has great application potential, and lays a good foundation for industrial production.

Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid

The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes likely generate a common active reagent, anhydrous HNO3. Kinetic and mechanistic studies have revealed that the reaction order in HNO3 is >2 and indicate that the ?NO2 radical is the active species.

Nucleophilic Fluorination of Heteroaryl Chlorides and Aryl Triflates Enabled by Cooperative Catalysis

Aryl and heteroaryl fluorides are growing to be dominant motifs in pharmaceuticals and agrochemicals, yet they are rare in both nature and commodity chemicals. As a consequence, there is an increasingly urgent need to develop mild, cost-effective, and scalable methods for fluorination. The most straightforward route to synthesize aryl fluorides is through the halide exchange "halex"reaction, but conditions, cost, and atom economy preclude most available methods from large-scale manufacturing processes. We report a new approach that leverages the cooperative action of 18-crown-6 ether and tetramethylammonium chloride to catalytically access the reactivity of tetramethylammonium fluoride and achieve halex fluorinations under mild conditions with operational ease. The described methodology readily converts both heteroaryl chlorides and aryl triflates to their corresponding (hetero)aryl fluorides in high yields and purities.