364-74-9

Basic information

• Product Name: 2,5-Difluoronitrobenzene
• Synonyms: 1,4-difluoro-2-nitro-benzen;Benzene, 1,4-difluoro-2-nitro-;2,5-DIFLUORONITROBENZENE;1,4-DIFLUORO-2-NITROBENZENE;AKOS BBS-00006468;2,5-Difluoro-1-nitrobenzene;Benzene, 1,4-difluoro-2-nitro- (6CI,7CI,8CI,9CI);3,5-diflurobenzalcohol
• CAS NO: 364-74-9
• Molecular Formula: C₆H₃F₂NO₂
• Molecular Weight: 159.09
• EINECS: 206-663-4
• Product Categories: HALIDE;Anilines, Aromatic Amines and Nitro Compounds;Miscellaneous;Fluorine series
• Mol File: 364-74-9.mol

Chemical Properties

• Melting Point: −11.7 °C(lit.)
• Boiling Point: 206.5 °C(lit.)
• Flash Point: 194 °F
• Appearance: Clear yellow/Liquid
• Density: 1.467 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000157mmHg at 25°C
• Refractive Index: n20/D 1.509(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: insoluble
• BRN: 2210200
• CAS DataBase Reference: 2,5-Difluoronitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Difluoronitrobenzene(364-74-9)
• EPA Substance Registry System: 2,5-Difluoronitrobenzene(364-74-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 2810
• WGK Germany: 3
• RTECS: CZ5715000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 364-74-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Difluoronitrobenzene is used as a synthetic intermediate for the production of N-alkylated 2-arylaminobenzimidazolesquinoxalinones. These compounds have potential applications in the development of new drugs and therapies.
Used in Chemical Research:
2,5-Difluoronitrobenzene is also used as a synthetic intermediate for the synthesis of N-(2-nitro-4-fluorophenyl)-1,2,3,4-tetrahydroisoquinoline. 2,5-Difluoronitrobenzene is of interest in chemical research due to its unique structure and potential applications in various fields.

InChI:InChI=1/C6H5FN2O2/c7-5-2-1-4(8)3-6(5)9(10)11/h1-3H,8H2

Upstream product

• 98-95-3 nitrobenzene 
• 540-36-3 para-difluorobenzene 
• 367-30-6 2,5-difluoroaniline 
• 97-00-7 1-chloro-2,4-dinitro-benzene 

Downstream Products

• 121845-35-0 5-(4-Fluoro-2-nitro-phenylamino)-3-methyl-3H-imidazole-4-carbonitrile 
• 79291-38-6 ethyl 3-<(4-fluoro-2-nitrophenyl)amino>-1-methylpyrazole-4-carboxylate 
• 107618-14-4 4-(4-fluoro-2-nitro-phenylamino)-piperidine-1-carboxylic acid ethyl ester 
• 136122-47-9 (3,4-Dichloro-benzyl)-(4-fluoro-2-nitro-phenyl)-amine 
• 147124-35-4 dimethyl 2-(4-fluoro-2-nitrophenyl)malonate 
• 191847-72-0 N-(4-fluoro-2-nitrophenyl)glycine methyl ester 
• 25373-42-6 1-(4-fluoro-2-niotrophenyl)-1H-imidazole 
• 704-05-2 (4-fluoro-2-nitrophenyl)-(methyl)amine 
• 887572-14-7 N-benzyl-4-fluoro-2-nitroaniline 
• 29397-70-4 2-<<(4-chlorophenyl)methyl>amino>-5-fluoroaniline 
• 144728-02-9 N¹-(4-Bromo-benzyl)-4-fluoro-benzene-1,2-diamine 
• 144728-12-1 4-fluoro-N₁-(4-methoxybenzyl)benzene-1,2-diamine 
• 136122-50-4 N¹-(3,4-Dichloro-benzyl)-4-fluoro-benzene-1,2-diamine 
• 144728-00-7 N¹-(4-Bromo-2-fluoro-benzyl)-4-fluoro-benzene-1,2-diamine 

Relevant articles and documents

A preparation method for 4-methoxy-2-nitrobenzoic acid

An industrial preparation method for 4-methoxy-2-nitrobenzoic acid is disclosed. In the method, p-difluorobenzene is adopted as an initial raw material and subjected to nitration, ammonolysis, diazotization bromination, cyaniding, methoxylation and hydrolysis which are six steps to synthesize the 4-methoxy-2-nitrobenzoic acid. The 4-methoxy-2-nitrobenzoic acid obtained by the method is white powdered solid with purity being 98.5%, the raw material conversion ratio in each step is 100%, and the total yield of the whole process is 35.8%.

Reactions of aromatic compounds with xenon difluoride

Reactions of substituted benzenes C6H5R (R = Me, F, Cl, Br, CF3, NO2) with xenon difluoride in the presence of boron trifluoride–diethyl ether complex in weakly acidic (1,1,1,3,3-pentafluorobutane) and weakly basic media (acetonitrile) have been studied. These reactions lead to the formation of fluorobenzene derivatives FC6H4R (isomer mixture) together with isomeric difluorobenzenes and fluorinated and non-fluorinated biphenyls. The results have been compared with previously reported data obtained in other solvents using other catalysts.

A high-output, continuous selective and heterogeneous nitration of p -difluorobenzene

A practical continuous nitration process for 2,5-difluoronitrobenzene via nitration of p-difluorobenzene with fuming nitric acid in 98% yield has been developed. The excellent yield of this liquid/liquid biphasic reaction resulted from the advantages of a continuous flow system. The 2.0 equiv sulfuric acid could be used three times directly with product yields in the range of 96-98%, and further recycling of waste acid could be partly achieved by adjusting the concentration of sulfuric acid. Reaction time could be brought down to 2 min by increasing the reaction temperature and thereby taking advantage of superior mass and heat transfer of this continuous flow system.

Sequential continuous flow processes for the oxidation of amines and azides by using HOF·MeCN

The generation and use of the highly potent oxidising agent HOF·MeCN in a controlled single continuous flow process is described. Oxidations of amines and azides to corresponding nitrated systems by using fluorine gas, water and acetonitrile by sequential gas-liquid/liquid-liquid continuous flow procedures are reported. Oxidation in flow: The oxidation of amines and azides to the corresponding nitrated systems by using fluorine gas, water and acetonitrile by sequential gas-liquid/liquid-liquid continuous flow procedures are reported. Copyright

BF3·2CF3CH2OH (BF 3·2TFE), an efficient superacidic catalyst for some organic synthetic transformations

BF3 · 2CF3CH2OH complex was found to be a very effective superacidic catalyst comparable in acid strength to at least that of 100% anhydrous sulfuric acid for various acid-catalyzed organic transformations such as isomerizations, rearrangements, ionic hydrogenation of various ketones, and aromatics with triethylsilane and nitration of aromatics with metal nitrate. Studies of the pivalaldehyde-methyl isopropyl ketone rearrangement and the benzopinacol to phenanthrene transformation suggest that the complex has an acidity comparable to that of 100% anhydrous sulfuric acid. The structure and properties of the 1:2 boron trifluoride-trifluoroethanol complex have been further studied using NMR (1H, 13C, 19F, 11B) and DFT calculations at the B3LYP/6- 311++G**//B3LYP/6-31G* level.

Ozone-mediated reaction of polychlorobenzenes and some related halogeno compounds with nitrogen dioxide: A novel non-acid methodology for the selective mononitration of moderately deactivated aromatic systems

In the presence of ozone and preferably methanesulfonic acid as catalyst, polychlorobenzenes undergo selective mononitration with nitrogen dioxide at low temperatures, giving the corresponding polychloronitrobenzenes, in most cases in nearly quantitative yields.

General and Highly Efficient Syntheses of m-Fluoro Arenes Using Potassium Fluoride-Exchange Method

Tetraphenylphosphonium bromide was found to be a suitable catalyst for the reaction of m-nitroaryl derivatives carrying cyano, nitro, chlorocarbonyl, trifluoromethyl, and chlorosulfonyl groups with potassium fluoride in the presence of a stoichiometric amount of phthaloyl dichloride, giving the corresponding m-fluoro aromatic derivatives in good yields.The catalyst was also found to be efficient for the fluorodesulfonylation of m-(fluorosulfonyl)aryl derivatives to afford m-fluoro arenes by the use of a reaction-distillation technique.

Tetraphenylphosphonium Bromide Catalyzed Fluorodenitrations and Fluorodesulfonylations. Efficient Syntheses of m-Fluoroaromatic Compounds

Meta-fluoroaromatic compounds were effectively synthesized from m-nitroaromatic or m-fluorosulfonylaromatic compounds by replacement reaction with potassium fluoride in the presence of a catalytic amount of tetraphenylphosphonium bromide.

2-(2,5-difluorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5 diones

Disclosed are herbicides of the formula: STR1 wherein R is H or halo of atomic weight of from 18 to 80.

Thieno[3,2-b]-[1,5]benzodiazepines

Thieno[1,5]benzodiazepines having useful CNS activity containing the novel tricyclic ring system: STR1 the 10-position being substituted by an amino, preferably a piperazino, group.