2369-11-1

Basic information

• Product Name: 5-Fluoro-2-nitroaniline
• Synonyms: 5-FLUORO-2-NITROANILINE;2-nitro-5-fluoroaniline;5-FLUORO-2-NITROBENZENAMINE;5-Fluoro-2-nitro-1-benzenamine;(5-fluoro-2-nitro-phenyl)amine;5-Fluoro-2-nitroanil;2-Amino-4-fluoronitrobenzene;BenzenaMine, 5-fluoro-2-nitro-
• CAS NO: 2369-11-1
• Molecular Formula: C₆H₅FN₂O₂
• Molecular Weight: 156.11
• EINECS: 219-128-5
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds
• Mol File: 2369-11-1.mol

Chemical Properties

• Melting Point: 96.0 to 100.0 °C
• Boiling Point: 295.5 °C at 760 mmHg
• Flash Point: 132.5 °C
• Appearance: /Solid
• Density: 1.448 g/cm³
• Vapor Pressure: 0.00152mmHg at 25°C
• Refractive Index: 1.603
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -1.36±0.25(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 5-Fluoro-2-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Fluoro-2-nitroaniline(2369-11-1)
• EPA Substance Registry System: 5-Fluoro-2-nitroaniline(2369-11-1)

Safety Data

• Hazard Codes: Xi,T
• Statements: 23/24/25-33-52/53-36/37/38
• Safety Statements: 28-36/37-45-61-24/25-22
• HazardClass: IRRITANT
• Hazardous Substances Data: 2369-11-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-Fluoro-2-nitroaniline is used as a chemical intermediate for the synthesis of various organic compounds. Its unique structure allows it to be a valuable building block in the creation of a wide range of products, including pharmaceuticals, dyes, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Fluoro-2-nitroaniline is used as a key intermediate in the development of new drugs. Its incorporation into drug molecules can potentially enhance their efficacy, selectivity, and pharmacokinetic properties, leading to improved therapeutic outcomes for patients.
Used in Dye Manufacturing:
5-Fluoro-2-nitroaniline is also utilized in the manufacturing of dyes, where its chemical properties contribute to the production of vibrant and stable colorants for various applications, such as textiles, plastics, and printing inks.
Used in Specialty Chemicals:
Furthermore, 5-Fluoro-2-nitroaniline finds application in the production of specialty chemicals, where its unique properties can be harnessed to create compounds with specific functionalities and applications, such as in the fields of agriculture, materials science, and environmental management.

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

Upstream product

• 351-28-0 N-(3-fluorophenyl)acetamide 
• 108-24-7 acetic anhydride 
• 372-19-0 meta-fluoroaniline 
• 100-52-7 benzaldehyde 
• 2106-50-5 2-chloro-4-fluoro-1-nitrobenzene 
• 446-35-5 2,4-Difluoronitrobenzene 
• 350-46-9 4-Fluoronitrobenzene 
• 555-24-8 lithium phenolate 
• 1121-69-3 lithium 4-methylphenoxide 
• 1122-94-7 lithium 4-methoxyphenoxide 
• 114299-85-3 lithium 4-fluorophenolate 
• 17162-41-3 2,4,6-trichlorosulfenamide 
• 67-62-9 O-Methylhydroxylamin 
• 865-47-4 potassium tert-butylate 

Downstream Products

• 20691-71-8 5-(dimethylamino)-2-nitroaniline 
• 345-14-2 N-methylcarbonyl 2-nitro-5-fluoroaniline 
• 118807-91-3 N-cyanomethyl-5-fluoro-2-nitroaniline 
• 131885-76-2 2-nitro-5-(1,2,4-triazol-1-yl)aniline 
• 123259-43-8 (5-Fluoro-2-nitro-phenyl)-carbamic acid (1R,3R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester; hydrochloride 
• 82711-97-5 5-fluoro-2-nitrobenzenesulfonyl chloride 
• 367-31-7 4-fluoro-1,2-phenylenediamine 
• 1026045-13-5 [4-(5-fluoro-2-nitro-phenylcarbamoyl)-benzyl]-carbamic acid pyridin-3-ylmethyl ester 
• 900506-32-3 2-nitro-5-(4-(piperidin-1-yl)piperidin-1-yl)benzenamine 
• 43210-66-8 3-amino-4-nitro-4'-hydroxydiphenyl ether 
• 668435-05-0 {[(2S,5R)-4-(3-amino-4-nitrophenyl)-5-methylmorpholin-2-yl]methyl}dimethylamine 
• 668435-01-6 {[(2R,5R)-4-(3-amino-4-nitrophenyl)-5-methylmorpholin-2-yl]methyl}dimethylamine 
• 1001414-69-2 C₁₄H₁₉N₃O₇ 
• 882803-25-0 4-(4-(piperidin-1-yl)piperidin-1-yl)benzene-1,2-diamine 

Relevant articles and documents

Zur Synthese sulfonierter Derivate von 4-Fluoranilin

Syntheses of Sulfonated Derivatives of 4-Fluoroaniline; Synthesis of 2-amino-5-fluorobenzenesulfonic acid (2) was achieved by baking the hydrogen sulfate of 4-fluoroaniline (1).Sulfonation of p-fluoroacetanilide (4) with oleum followed by hydrolysis gave 5-amino-2-fluorobenzenesulfonic acid (3).The same reaction with 1 yielded 3 in an impure state.The structures of 2 and 3 were confirmed by converting the diazonium chlorides derived from 5-fluoro-2-nitroaniline (5) and from 2-fluoro-5-nitroaniline (8) to 5-fluoro-2-nitrobenzenesulfonyl chloride (6) and 2-fluoro-5-nitrobenzenesulfonyl chloride (9), respectively, followed by hydrolysis of 6 to 5-fluoro-2-nitrobenzenesulfonic acid (7), and of 9 to 2-fluoro-5-nitrobenzenesulfonic acid (10), and by final reduction.Compound 10 was also obtained by sulfonation of 1-fluoro-4-nitrobenzene (11) with oleum.

A Metal-Free Direct Arene C?H Amination

The synthesis of aryl amines via the formation of a C?N bond is an essential tool for the preparation of functional materials, active pharmaceutical ingredients and bioactive products. Usually, this chemical connection is only possible by transition metal-catalyzed reactions, photochemistry or electrochemistry. Here, we report a metal-free arene C?H amination using hydroxylamine derivatives under benign conditions. A charge transfer interaction between the aminating reagents TsONHR and the arene substrates enables the chemoselective amination of the arene, even in the presence of various functional groups. Oxygen was crucial for an effective conversion and its accelerating role for the electron transfer step was proven experimentally. In addition, this was rationalized by a theoretical study which indicated the involvement of a dioxygen-bridged complex with a “Sandwich-like” arrangement of the aromatic starting materials and the aminating agents at the dioxygen molecule. (Figure presented.).

From methylene bridged diindole to carbonyl linked benzimidazoleindole: Development of potent and metabolically stable PCSK9 modulators

Proprotein convertase subtilisin/kexin type 9 (PCSK9) is a recently validated therapeutic target for lowering low-density lipoprotein cholesterol (LDL-C). Through phenotypic screening, we previously discovered a class of small-molecules with a 2,3′-diindolymethane (DIM) skeleton that can decrease the expression of PCSK9. But these compounds have low potency and low metabolically stability. After performing structure-activity relationship (SAR) optimization by nitrogen scan, deuterium substitution and fluorine scan, we identified a series of much more potent and metabolically stable PCSK9 modulators. A preliminary in vivo pharmacokinetic study was performed for representative analogues difluorodiindolyketone (DFDIK) 12 and difluorobenzoimidazolylindolylketone (DFBIIK-1) 13. The in vitro metabolic stability correlate well with the in vivo data. The most potent compound 21 has the EC50 of 0.15 nM. Our SAR studies also indicated that the NH on the indole ring of 21 can tolerate more function groups, which may facilitate the mechanism of action studies and also allow further improvement of the pharmacological properties.

5-fluoro-2-nitrophenol preparation method

The invention belongs to the field of organic synthesis, and particularly relates to a 5-fluoro-2-nitrophenol preparation method. In the prior art, the existing synthesis method has disadvantages of low conversion rate and long reaction time so as not to easily achieve industrial operation. A purpose of the present invention is to solve the technical problem in the prior art. The technical schemeis to provide a 5-fluoro-2-nitrophenol preparation method, which comprises: a) carrying out a reaction on 2,4-difluoronitrobenzene and NH 3 to obtain 5-fluoro-2-nitroaniline; and b) carrying out a reaction on the 5-fluoro-2-nitroaniline under the actions of sulfuric acid and sodium nitrite to obtain the 5-fluoro-2-nitrophenol. According to the present invention, the 5-fluoro-2-nitrophenol preparation method has advantages of good selectivity, almost no side reaction, high yield, short reaction time, simple operation and easy industrialization.

Fluorinated 2-Amino-4-(Benzylamino)Phenylcarbamate Derivatives

The invention relates to fluorinated compounds and their use as anti-epileptic, muscle-relaxing, fever-reducing and peripherally analgesically acting medications and as imaging agents. Novel fluorinated 2-amino-4-(benzylamino)phenyl carbamate derivatives of ezogabine and pharmaceutically acceptable salts or solvates thereof and their use are described.

The kinetics and mechanisms of aromatic nucleophilic substitution reactions in liquid ammonia

The rates of aromatic nucleophilic substitution reactions in liquid ammonia are much faster than those in protic solvents indicating that liquid ammonia behaves like a typical dipolar aprotic solvent in its solvent effects on organic reactions. Nitrofluorobenzenes (NFBs) readily undergo solvolysis in liquid ammonia and 2-nitrofluorobenzene is about 30 times more reactive than the 4-substituted isomer. Oxygen nucleophiles, such as alkoxide and phenoxide ions, readily displace fluorine of 4-NFB in liquid ammonia to give the corresponding substitution product with little or no competing solvolysis product. Using the pKa of the substituted phenols in liquid ammonia, the Bronsted βnuc for the reaction of 4-NFB with para-substituted phenoxides is 0.91, indicative of the removal of most of the negative charge on the oxygen anion and complete bond formation in the transition state and therefore suggests that the decomposition of the Meisenheimer σ-intermediate is rate limiting. The aminolysis of 4-NFB occurs without general base catalysis by the amine and the second-order rate constants generate a Bronsted βnuc of 0.36 using either the pKa of aminium ion in acetonitrile or in water, which is also interpreted in terms of rate limiting breakdown of the Meisenheimer σ-intermediate. Nitrobenzene and diazene are formed as unusual products from the reaction between sodium azide and 4-NFB, which may be due to the initially formed 4-nitroazidobenzene decomposing to give a nitrene intermediate, which may then give diazene or be trapped by ammonia to give the unstable hydrazine which then yields nitrobenzene.

The [Cu]-catalyzed SNAR reactions: Direct amination of electron deficient aryl halides with sodium azide and the synthesis of arylthioethers under Cu(II) - Ascorbate redox system

A one pot [Cu]-promoted SNAr reaction of electron-deficient halobenzenes with sodium azide and the reduction of the intermediate aryl azides under the same Cu(II)-ascorbate redox conditions leading to anilines has been documented. Control experiments revealed that both ascorbate and proline play important role in the reaction path way. Further, the use of this catalytic Cu(II)-ascorbate redox system has been explored for the synthesis of arylthioethers.

Combination therapy with CHK1 inhibitors

Compounds of Structure I, and salts, tautomers, stereoisomers, and mixtures thereof may be used in methods of inhibiting checkpoint kinase 1 in subjects, in methods for inducing cell cycle progression, and in methods for increasing apoptosis in cells. Such compounds may be used to prepare pharmaceutical compositions and may be used in conjunction with DNA damaging agents.

Inhibition of FGFR3 and treatment of multiple myeloma

Methods of inhibiting fibroblast growth factor receptor 3 and treating various conditions mediated by fibroblast growth factor receptor 3 are provided that include administering to a subject a compound of Structure I, a pharmaceutically acceptable salt thereof, a tautomer thereof, or a pharmaceutically acceptable salt of the tautomer. Compounds having the Structure I have the following structure where and have the variables described herein. Such compounds may be used to prepare medicaments for use in inhibiting fibroblast growth factor receptor 3 and for use in treating conditions mediated by fibroblast growth factor receptor 3 such as multiple myeloma.

Hyperbranched polyphenylquinoxalines from self-polymerizable AB 2 and A2B monomers

A self-polymerizable AB2 monomer, 2,3-bis(4-hydroxyphenyl)-6-fluoroquinoxaline, and an A2B monomer, 2,3-bis(4-fluorophenyl)-6-(4-hydrcixyphenoxy)quinoxaline) were prepared and polymerized to afford phenol-terminated and aryl fluoride terminated, hyperbranched polyphenylquinoxalines (HPPQs), respectively. MALDI-TOF analysis showed that intramolecular cyclization was a dominant process for the low molecular weight portion during the polymerizations. After isolation and complete dryness, the phenol-terminated HPPQ 1 was only soluble in strong organic acids, while the aryl fluoride terminated HPPQ 2 was soluble in most common organic solvents. HPPQ 1 was treated with allyl bromide to afford an allyl ether terminated HPPQ 3, which was also soluble in most organic solvents. Intrinsic viscosity measurements and SEC analysis indicated that HPPQ 2 had a much higher Mw and a much broader molecular weight distribution (PDI ～ 60) than HPPQ 1 and HPPQ 3 (PDI ～ 4). The results also suggested that HPPQ 1 formed aggregates in solution and that HPPQ 2 had a much more extended and open conformation. All the HPPQs, which were highly fluorescent, had UV absorption maxima near 375 nm in THF. However, the wavelength of their emission maxima, which ranged from 424 to 466 nm, depended on their end groups.