53981-24-1

Usage

Uses

Used in Chemical Synthesis:
2-Amino-5-fluorophenol is used as an organic intermediate for the synthesis of various compounds. Its unique structure allows it to be a key component in the production of different chemicals.
Used in Analytical Chemistry:
2-Amino-5-fluorophenol is used as a precursor for the synthesis of indicators used in the determination of Mg2+ ions by Nuclear Magnetic Resonance (NMR) spectroscopy. 2-Amino-5-fluorophenol serves as a starting material for the preparation of (2-amino-5-fluorophenol-N, N, O-triacetic acid trimethyl ester), which is an intermediate in the development of such indicators.
In the synthesis of this intermediate, three feasible reactions have been experimentally carried out, including alkaline hydrolysis, catalytic hydrogenation, and esterification. These reactions highlight the versatility of 2-Amino-5-fluorophenol in chemical processes and its importance in the development of analytical tools for detecting specific ions.

InChI:InChI=1/C9H8F3NO2/c10-9(11,12)7-3-1-6(5-13-7)2-4-8(14)15/h1,3,5H,2,4H2,(H,14,15)

Upstream product

• 446-36-6 5-fluoro-2-nitrophenol 
• 367-25-9 2,4-difluorophenylamine 
• 127682-43-3 O-(3-fluorophenyl)hydroxylamine 

Downstream Products

• 112808-67-0 2-(2-bromo-3-methylbutyryl)amino-5-fluorophenol 
• 201138-84-3 diethyl N-(2-hydroxy-4-fluorophenyl)aminomethylenemalonate 
• 135838-04-9 6-fluoroquinolin-8-ol 
• 145096-57-7 6-fluoro-1,3-benzoxazole-2-thiol 
• 10189-45-4 2-chloro-N-(2-hydroxyphenyl)nicotinamide 
• 134894-49-8 6-methylbenzo[b]pyrido[3,2-f ][1,4]oxazepin-5(6H)-one 
• 134894-51-2 10-Allyl-10H-5-oxa-4,10-diaza-dibenzo[a,d]cyclohepten-11-one 
• 134894-50-1 10-Ethyl-10H-5-oxa-4,10-diaza-dibenzo[a,d]cyclohepten-11-one 
• 140413-12-3 7-Fluoro-10-methyl-10H-5-oxa-4,10-diaza-dibenzo[a,d]cyclohepten-11-one 
• 503149-75-5 1-benzyloxycarbonyl-4-(6-fluoro-2-benzoxazolyl)piperidine 
• 2923-94-6 6-fluoro-3H-benzooxazol-2-one 
• 137472-06-1 2-chloro-N-(4-fluoro-2-hydroxyphenyl)acetamide 
• 16323-08-3 2-acetamido-5-fluorophenol 
• 103361-99-5 7-fluoro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine 

Relevant academic research and scientific papers

HMOX1 inducers

The present invention is related to compounds of structure (I) as heme oxygenase 1 (HMOX 1) inducers. The present invention is also related a method of controlling the activity or the amount, or both the activity and the amount, of heme-oxygenase 1 in a mammalian subject. The definitions of the variables are provided herein.

Benzothiazolyl ureas are low micromolar and uncompetitive inhibitors of 17Β-HSD10 with implications to Alzheimer’s disease treatment

Human 17β-hydroxysteroid dehydrogenase type 10 is a multifunctional protein involved in many enzymatic and structural processes within mitochondria. This enzyme was suggested to be involved in several neurological diseases, e.g., mental retardation, Parkinson’s disease, or Alzheimer’s disease, in which it was shown to interact with the amyloid-beta peptide. We prepared approximately 60 new compounds based on a benzothiazolyl scaffold and evaluated their inhibitory ability and mechanism of action. The most potent inhibitors contained 3-chloro and 4-hydroxy substitution on the phenyl ring moiety, a small substituent at position 6 on the benzothiazole moiety, and the two moieties were connected via a urea linker (4at, 4bb, and 4bg). These compounds exhibited IC50 values of 1–2 μM and showed an uncompetitive mechanism of action with respect to the substrate, acetoacetyl-CoA. These uncompetitive benzothiazolyl inhibitors of 17β-hydroxysteroid dehydrogenase type 10 are promising compounds for potential drugs for neurodegenerative diseases that warrant further research and development.

Hyperbranched Poly(ester-enamine) from Spontaneous Amino-yne Click Reaction for Stabilization of Gold Nanoparticle Catalysts

Hyperbranched polymers have garnered much attention due to attractive properties and wide applications, such as drug-controlled release, stimuli-responsive nano-objects, photosensitive materials and catalysts. Herein, two types of novel hyperbranched poly(ester-enamine) (hb-PEEa) were designed and synthesized via the spontaneous amino-yne click reaction of A2 monomer (1, 3-bis(4-piperidyl)-propane (A2a) or piperazine (A2b)) and B3 monomer (trimethylolpropanetripropiolate). According to Flory's hypothesis, gelation is an intrinsic problem in an ideal A2+B3 polymerization system. By controlling the polymerization conditions, such as monomer concentration, molar ratio and rate of addition, a non-ideal A2+B3 polymerization system can be established to avoid gelation and to synthesize soluble hb-PEEa. Due to abundant unreacted alkynyl groups in periphery, the hb-PEEa can be further functionalized by different amino compounds or their derivates. The as-prepared amphiphilic PEG-hb-PEEa copolymer can readily self-assemble into micelles in water, which can be used as surfactant to stabilize Au nanoparticles (AuNPs) during reduction of NaBH4 in aqueous solution. As a demonstration, the as-prepared PEG-hb-PEEa-supported AuNPs demonstrate good dispersion in water, solvent stability and remarkable catalytic activity for reduction of nitrobenzene compounds.

Synthesis, docking, 3-D-qsar, and biological assays of novel indole derivatives targeting serotonin transporter, dopamine D2 receptor, and mao-a enzyme: In the pursuit for potential multitarget directed ligands

A series of 27 compounds of general structure 2,3-dihydro-benzo[1,4]oxazin-4-yl)-2-{4-[3-(1H-3indolyl)-propyl]-1-piperazinyl}-ethanamides, Series I: 7(a-o) and (2-{4-[3-(1H-3-indolyl) -propyl]-1-piperazinyl}-acetylamine)-N-(2-morfolin-4-yl-ethyl)-fluorinated benzamides Series II: 13(a-l) were synthesized and evaluated as novel multitarget ligands towards dopamine D2 receptor, serotonin transporter (SERT), and monoamine oxidase-A (MAO-A) directed to the management of major depressive disorder (MDD). All the assayed compounds showed affinity for SERT in the nanomolar range, with five of them displaying Ki values from 5 to 10 nM. Compounds 7k, Ki = 5.63 ± 0.82 nM, and 13c, Ki = 6.85 ± 0.19 nM, showed the highest potencies. The affinities for D2 ranged from micro to nanomolar, while MAO-A inhibition was more discrete. Nevertheless, compounds 7m and 7n showed affinities for the D2 receptor in the nanomolar range (7n: Ki = 307 ± 6 nM and 7m: Ki = 593 ± 62 nM). Compound 7n was the only derivative displaying comparable affinities for SERT and D2 receptor (D2/SERT ratio = 3.6) and could be considered as a multitarget lead for further optimization. In addition, docking studies aimed to rationalize the molecular interactions and binding modes of the designed compounds in the most relevant protein targets were carried out. Furthermore, in order to obtain information on the structure-activity relationship of the synthesized series, a 3-D-QSAR CoMFA and CoMSIA study was conducted and validated internally and externally (q2 = 0.625, 0.523 for CoMFA and CoMSIA and r2ncv = 0.967, 0.959 for CoMFA and CoMSIA, respectively).

SUBSTITUTED 2-AZABICYCLO[3.1.1]HEPTANE AND 2-AZABICYCLO[3.2.1]OCTANE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS

There is provided a compound of formula (I), wherein L1 to L3, R1 to R4, X, A and B have meanings given in the description, and pharmaceutically acceptable salts, solvates and prodrugs thereof, which compounds are useful as antagonists of the orexin-1 and orexin-2 receptors or as selective antagonists of the orexin-1 receptor, and thus, in particular, in the treatment or prevention of inter alia substance dependence, addiction, anxiety disorders, panic disorders, binge eating, compulsive disorders, impulse control disorders, cognitive impairment and Alzheimer's disease.

Synthesis and biological evaluation of potential acetylcholinesterase inhibitors based on a benzoxazine core

With the purpose of expanding the structural variety of chemical compounds available as pharmacological tools for the treatment of Alzheimer's disease, we synthesized and evaluated a novel series of indole-benzoxazinones (Family I) and benzoxazine-arylpiperazine derivatives (Family II) for potential human acetylcholinesterase (hAChE) inhibitory properties. The most active compounds 7a and 7d demonstrated effective inhibitory profiles with Ki values of 20.3 ± 0.9 μM and 20.2 ± 0.9 μM, respectively. Kinetic inhibition assays showed non-competitive inhibition of AChE by the tested compounds. According to our docking studies, the most active compounds from both series (Families I and II) showed a binding mode similar to donepezil and interact with the same residues.

Constructing magnetic Si-C-Fe hybrid microspheres for room temperature nitroarenes reduction

In this work, we present, for the first time, the synthesis and characterization of magnetic Si-C-Fe hybrid microspheres and their catalytic performance in room temperature reduction of 4-nitrophenol as a representative sustainable process for converting environmental pollutants to fine chemicals. The ferrocene-modified polydivinylbenzene (Fc-PDVB) precursor was synthesized by Pt-catalyzed hydrosilylation between the residual vinyl groups on the PDVB surface and 1,1′-bis (dimethylsilyl)ferrocene, where further pyrolysis led to the formation of Fe nanocrystal-containing Si-C-Fe hybrid microspheres. The precursor and hybrid microspheres were characterized by transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), BET surface area/porosity, powder X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), magnetic properties and MAS solid-state NMR measurements. The ultimate microspherical catalyst exhibited nano- and meso-pores, a high specific surface area (i.e., 347.9 m2 g-1) and good ferromagnetic properties. Efficient catalytic activity (TOF: 0.163 s-1), 100% selectivity (to 4-aminophenol) and excellent reusability (with easy separation) have been delivered. The achieved microspheres outperform a number of nanomaterials such as supported noble metal particles, composites, monoliths and sheets. We have confirmed by DFT calculations that the activation of 4-nitrophenol via its weak non-covalent interaction with the sp2 carbon domain of Si-C-Fe hybrid microspheres contributed to the superior performance which can be extended to a range of nitrobenzenes.

Synthesis of 7 - fluoro - 6 - amino - 2 H - 1, 4 - benzoxazine - 3 (4 H) - one method (by machine translation)

The invention discloses a method for synthesizing 7 - fluoro - 6 - amino - 2 H - 1, 4 - benzoxazine - 3 (4 H) - one method, in order to 2, 4 - difluoroaniline as raw materials, through the substituted by hydroxyl, ether, nitration, hydrogenation reduction reaction to obtain the 7 - fluoro - 6 - amino - 2 H - 1, 4 - benzoxazine - 3 (4 H) - ketone (methylacetylene comprising diflufenican intermediate). Synthesis method of the invention, in order to 2, 4 - difluoroaniline as raw materials, cheap and easy to obtain, to a certain extent reduces the production cost; intermediate 1 without going through the high-pressure hydrogenation reaction can be with the chloroethyl acetate reaction ring, reduce the risk of the reaction; the nitration reaction is easy to control, decreasing the reaction, little impurity, raise the yield; hydrogenation reaction catalyst can be recovered, recycled, and reducing the cost; in addition the raw material is cheap, mild reaction, simple operation, facilitates large scale production. (by machine translation)

ANTI-TRICHOPHYTIC ADHESIVE PATCH

According to the present invention, a patch for nail and/or skin having antifungal activity against dermatophytes, and having higher nail permeability can be provided. The patch for nail and/or skin for prevention or treatment of dermatophytosis comprises in a pressure sensitive adhesive layer a compound represented by the formula: wherein R1 represents a hydrogen atom, C1-6 alkyl, or trifluoromethyl; R2 represents a hydrogen atom, C1-6 alkyl, halogen, -COO(C1-6 alkyl), or (CH2)1-3COOR (R represents a hydrogen atom or C1-6 alkyl); R3 represents a hydrogen atom, C1-6 alkyl, amino, trifluoromethyl, or OR (R represents a hydrogen atom or C1-6 alkyl); R4 represents a hydroxyl group; R5 represents a hydrogen atom, C1-6 alkyl, a hydroxyl group, or halogen; R6 represents a hydrogen atom, C1-6 alkyl, trifluoromethyl, halogen, amino, -NRaRb, nitro, hydroxy-C1-6 alkyl, -CONRaRb, -COO(C1-6 alkyl), -COOH, -(CH2)1-3COOR, or ORa (R represents a hydrogen atom or C1-6 alkyl, Ra and Rb may be the same or different from each other, and each represent a hydrogen atom, C1-6 alkyl, or C1-6 acyl); R7 represents a hydrogen atom, C1-6 alkyl, -OR (R represents a hydrogen atom or C1-6 alkyl), or halogen; and R8 represents a hydrogen atom, C1-6 alkyl, a hydroxyl group, amino, or nitro, or a salt thereof.

PATCH FOR ANTI-DERMATOPHYTOSIS

A patch for nails or skin for prevention or treatment of dermatophytosis, containing a layer including a pressure sensitive adhesive layer and a compound represented by the formula: wherein R1 represents hydrogen, C1-16 alkyl, or trifluoromethyl; R2 represents hydrogen, C1-6 alkyl, halogen, —COO(C1-6 alkyl), or (CH2)1-3COOR; R3 represents hydrogen, C1-6 alkyl, amino, trifluoromethyl, or OR; R4 represents hydroxyl; R5 represents hydrogen, C1-6 alkyl, hydroxyl, or halogen; R6 represents hydrogen, C1-6 alkyl, trifluoromethyl, halogen, amino, —NRaRb, nitro, hydroxy-C1-6 alkyl, —CONRaRb, —COO(C1-6 alkyl), —COOH, —(CH2)1-3COOR, or ORa (Ra and Rb each represents hydrogen, C1-6 alkyl, or C1-6 acyl); R7 represents hydrogen, C1-6 alkyl, —OR, or halogen; R8 represents hydrogen, C1-6 alkyl, hydroxyl, amino, or nitro; and R represents hydrogen or C1-6 alkyl; or a salt thereof.