62257-16-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Amino-4-fluorophenol is utilized as a key intermediate in the synthesis of pharmaceuticals. Its presence in the molecular structure of certain drugs aids in enhancing their therapeutic properties and effectiveness.
Used in Dye Industry:
In the dye industry, 3-Amino-4-fluorophenol is employed as a precursor for the production of various dyes. Its unique chemical structure contributes to the color and stability of the dyes, making it an essential component in this sector.
Used in Organic Chemistry Research:
3-Amino-4-fluorophenol is used as a reagent in organic chemistry research to introduce amino and fluorine functional groups into other molecules. This capability is crucial for the development of new organic compounds and the advancement of chemical technologies.
Used in Material Science:
3-Amino-4-fluorophenol has potential applications in the development of new materials. Its unique properties can be harnessed to create innovative materials with specific characteristics for various applications.

Upstream product

• 75001-47-7 N-(5-amino-2-fluorophenyl)acetamide 
• 454-07-9 N-(2-fluoro-5-nitrophenyl)acetamide 
• 369-36-8 6-fluoro-3-nitroaniline 
• 84478-75-1 2-chloro-4-fluoro-5-nitrophenol 
• 84478-89-7 2-chloro-4-fluoro-5-nitro-methoxycarbonyloxybenzene 
• 84478-88-6 2-chloro-4-fluoro-methoxycarbonyloxybenzene 
• 1996-41-4 2-chloro-4-fluorophenol 
• 1228996-49-3 2-fluoro-5-hydroxy-N-(trifluoroacetyl)aniline 
• 2105-96-6 4-fluoro-3-nitrophenol 

Downstream Products

• 1020173-02-7 5-(3-amino-4-fluorophenoxy)picolinonitrile 
• 1020173-04-9 2-fluoro-5-(2-(methylthio)pyrimidin-4-yloxy)benzenamine 
• 1020173-08-3 2-fluoro-5-(6-(trifluoromethyl)pyridin-3-yloxy)benzenamine 
• 1020173-36-7 5-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)pyrimidin-2-yloxy)-2-fluorobenzenamine 
• 143661-65-8 2-fluoro-5-cyclopentyloxyaniline 
• 932708-75-3 2-(2,4-dichlorobenzyl)-N-(2-fluoro-5-hydroxyphenyl)-3-oxobutyramide 
• 1092394-25-6 3-[(tert-butoxycarbonyl)amino]-4-fluorophenyl tert-butylcarbonate 
• 1005781-39-4 N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide 
• 1005779-75-8 N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]-2-methylcyclopropanecarboxamide 
• 1005784-06-4 N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]acetamide 
• 1125632-14-5 2-chloro-3-(1-cyanocyclopropyl)-N-(2-fluoro-5-hydroxyphenyl)benzamide 
• 1092394-11-0 ethyl {[5-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}-4-fluorophenoxy)pyridine-2-yl]carbamothioyl}carbamate 
• 1092394-01-8 N-{5-[(6-aminopyridin-3-yl)oxy]-2-fluorophenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide 
• 1092394-02-9 N-{2-fluoro-5-[(6-nitropyridin-3-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide 

Relevant academic research and scientific papers

POLYAROMATIC UREA DERIVATIVES AND THEIR USE IN THE TREATMENT OF MUSCLE DISEASES

The current invention provides urea derivatives, in particular compounds having the core structure heteroaryl-NH-CO-NH-aryl-O- heteroaryl, for use in treating, ameliorating, delaying, curing and/ or preventing a disease or condition associated with muscle cells and/or satellite cells, such as Duchenne muscular dystrophy, Becker muscular dystrophy, cachexia or sarcopenia.

Preparation method of 3-amino-4-fluorophenol

The invention provides a preparation method of 3-amino-4-fluorophenol. The preparation method comprises the following steps of mixing 2-bromo-2-fluoro-5-nitrophenoxy ethyl formate, an alkaline matter, a hydrogenation catalyst and an organic solvent, so as to obtain a mixture; introducing hydrogen into the mixture to perform hydrogenation reaction under the sealing condition, so as to obtain the 3-amino-4-fluorophenol, wherein before the hydrogen is introduced, the air in a sealed system is exhausted out. The preparation method has the advantages that the synthesis route is short, and fewer steps are adopted; only one-step reaction is required for the 2-bromo-2-fluoro-5-nitrophenoxy ethyl formate to synthesize the 3-amino-4-fluorophenol, and the amount of three wastes produced in the reaction process is fewer; by simply separating the synthesized product, the product with purity not less than 99% can be obtained, and the yield rate is high.

SUBSTITUTED PYRIDOBENZODIAZEPINONE-DERIVATIVES AND USE THEREOF

The present application relates to novel (3-hydroxyphenyl)amino-substituted pyrido[2,3-b][1,5]benzodiazepin-5-one derivatives, to processes for preparation thereof, to the use thereof alone or in combination for treatment and/or prevention of diseases and to the use thereof for production of medicaments for treatment and/or prevention of diseases, especially of angiogenic disorders and hyperproliferative disorders in which neovascularization plays a role, for example ophthalmological disorders and cancers and tumours. Such treatments can be effected as monotherapy or else in combination with other medicaments or further therapeutic measures.

Fluorinated rhodamines as photostable fluorescent dyes for labelling and imaging techniques

The present invention relates to novel fluorinated 3,6-diaminoxanthene compounds derived from the basic structural formula (I) and to their uses as photostable fluorescent dyes, e.g. for immunostainings and spectroscopic and microscopic applications, in particular in conventional microscopy, stimulated emission depletion (STED) reversible saturable optically linear fluorescent transitions (RESOLFT) microscopy, and fluorescence correlation spectroscopy. The claimed compounds are also useful as molecular probes in various spectroscopic applications.

Development of a scalable synthesis of a vascular endothelial growth factor receptor-2 kinase inhibitor: Efficient construction of a 6-etherified [1,2,4]triazolo[1,5-a]pyridine-2-amine Core

A practical and scalable synthesis of the vascular endothelial growth factor receptor-2 (VEGFR-2) kinase inhibitor 1 has been developed. The key features of the process development include facile preparation of the key raw material 3-amino-4- fluorophenol, chemoselective nucleophilic aromatic substitution of 5-chloro-2-nitropyridine with phenol, a safe one-pot synthesis of a substituted urea using an isothiocyanate generated in situ from inexpensive materials, and improvement of the yield of acylation in the end game. The optimized six-step synthesis afforded 1·H2O in 54% overall yield, twice as much as the yield of the original synthesis, without chromatographic purification. In addition, a robust recrystallization procedure to afford the desired crystal form of 1 was also developed.

METHODS AND COMPOSITIONS FOR THE TREATMENT OF MYELOPROLIFERATIVE DISEASES AND OTHER PROLIFERATIVE DISEASES

Compounds of the present invention find utility in the treatment of hyperproliferative diseases, mammalian cancers and especially human cancers including but not limited to malignant, melanomas, glioblastomas, ovarian cancer, pancreatic cancer, prostate cancer, lung cancers, breast cancers, kidney cancers, cervical carcinomas, metastasis of primary tumor sites secondary sites, myeloproliferative diseases, chronic myelogenous leukemia, acute lymphocytic leukemia, papillary thyroid carcinoma, non small cell lung cancer, mesothelioma, hypereosinophilic syndrome, gastrointestinal stromal tumors, colonic cancers, thyroid cancer, ocular diseases characterized by hyperproliferation leading to blindness including various retinopathies, i.e. diabetic retinopathy and age-related macular degeneration, rheumatoid arthritis, asthma, chronic obstructive pulmonary disease, human inflammation, rheumatoid spondylitis, ostero-arthritis, asthma, gouty arthritis, sepsis, septic shock, endotoxic shock, Gram-negative sepsis, toxic shock syndrome, adult respiratory distress syndrome, stroke, reperfusion injury, neural trauma, neural ischemia, psoriasis, restenosis, chronic obstructive pulmonary disease, bone resorptive diseases, graft-versus-host reaction, Crohn's disease, ulcerative colitis, inflammatory bowel disease, pyresis, and combinations thereof, a disease caused by c-ABL kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, c-KIT kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, VEGFR kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, PDGFR kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, FLT-3 kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, TIE-2 kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, TRK kinases, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, c-MET kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, or a disease caused by a HER kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof.

NOVEL FLUORINATED RHODAMINES AS PHOTOSTABLE FLUORESCENT DYES FOR LABELLING AND IMAGING TECHNIQUES

The present invention relates to novel fluorinated 3,6-diaminoxanthene compounds derived from the basic structural formula (I) and to their uses as photostable fluorescent dyes, e.g. for immunostainings and spectroscopic and microscopic applications, in particular in conventional microscopy, stimulated emission depletion (STED) reversible saturable optically linear fluorescent transitions (RESOLFT) microscopy, and fluorescence correlation spectroscopy. The claimed compounds are also useful as molecular probes in various spectroscopic applications.

New fluorinated rhodamines for optical microscopy and nanoscopy

New photostable rhodamine dyes represented by the compounds 1a-r and 3-5 are proposed as efficient fluorescent markers with unique combination of structural features. Unlike rhodamines with monoalkylated nitrogen atoms, N′,N-bis(2,2,2-trifluoroethyl) derivatives 1e, 1i, 1j, 3-H and 5 were found to undergo sulfonation of the xanthene fragment at the positions 4′ and 5′. Two fluorine atoms were introduced into the positions 2′ and 7′ of the 3′,6′-diaminoxanthene fragment in compounds 1a-d, 1i-l and 1m-r. The new rhodamine dyes may be excited with λ= 488 or 514 nm light; most of them emit light at λ = 512-554 nm (compounds 1q and 1r at λ=576 and 589 nm in methanol, respectively) and have high fluorescence quantum yields in solution (up to 98%), relatively long excited-state lifetimes (>3ns) and are resistant against photobleaching, especially at high laser intensities, as is usually applied in confocal microscopy. Sulfonation of the xanthene fragment with 30% SO3 in H2SO4 is compatible with the secondary amide bond (rhodamine-CON(Me)CH2CH 2COOH) formed with MeNHCH2CH2COOCH3 to providing the sterically unhindered carboxylic group required for further (bio)conjugation reactions. After creating the amino reactive sites, the modified derivatives may be used as fluorescent markers and labels for (bio)molecules in optical microscopy and nanoscopy with very-high light intensities. Further, the new rhodamine dyes are able to pass the plasma membrane of living cells, introducing them as potential labels for recent live-cell-tag approaches. We exemplify the excellent performance of the fluorinated rhodamines in optical microscopy by fluorescence correlation spectroscopy (FCS) and stimulated emission depletion (STED) nanoscopy experiments.

NOVEL FLUORINATED RHODAMINES AS PHOTOSTABLE FLUORESCENT DYES FOR LABELLING AND IMAGING TECHNIQUES

The present invention relates to novel fluorinated 3,6- diaminoxanthene compounds derived from the basic structural formula (I) and to their uses as photostable fluorescent dyes, e.g. for immunostainings and spectroscopic and microscopic applications, in particular in conventional microscopy, stimulated emission depletion (STED) reversible saturable optically linear fluorescent transitions (RESOLFT) microscopy, and fluorescence correlation spectroscopy. The claimed compounds are also useful as molecular probes in various spectroscopic applications.

CYCLOPROPANE AMIDES AND ANALOGS EXHIBITING ANTI-CANCER AND ANTI-PROLIFERATIVE ACTIVITIES

Compounds of the present invention find utility in the treatment of mammalian cancers and especially human cancers including, but not limited to, malignant melanomas, solid tumors, glioblastomas, ovarian cancer, pancreatic cancer, prostate cancer, lung cancers, breast cancers, kidney cancers, hepatic cancers, cervical carcinomas, metastasis of primary tumor sites, myeloproliferative diseases, chronic myelogenous leukemia, leukemias, papillary thyroid carcinoma, non-small cell lung cancer, mesothelioma, hypereosinophilic syndrome, gastrointestinal stromal tumors, colonic cancers, ocular diseases characterized by hyperproliferation leading to blindness including various retinopathies, diabetic retinopathy, rheumatoid arthritis, asthma, chronic obstructive pulmonary disease, mastocytosis, mast cell leukemia, and diseases caused by PDGFR-α kinase, PDGFR-β kinase, c-KIT kinase, cFMS kinase, c-MET kinase, and oncogenic forms, aberrant fusion proteins and polymorphs of any of the foregoing kinases.