103068-41-3

Usage

Uses

1. Used in Chemical Synthesis:
4-Fluoro-1,3-benzenediol is used as a reagent in the preparation of fluorescent dyes and indicators. Its unique structure allows for the development of novel compounds with enhanced properties, such as improved fluorescence and selectivity, which can be utilized in various analytical and diagnostic applications.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Fluoro-1,3-benzenediol is used as a key intermediate in the synthesis of various drugs and drug candidates. Its presence in the molecular structure can influence the pharmacological properties of the final product, such as potency, selectivity, and bioavailability.
3. Used in Material Science:
4-Fluoro-1,3-benzenediol can be employed in the development of new materials with specific properties, such as optical, electronic, or magnetic characteristics. Its incorporation into polymers or other materials can lead to the creation of novel materials with improved performance in various applications, including sensors, displays, and energy storage devices.
4. Used in Environmental Applications:
4-Fluoro-1,3-benzenediol can be utilized in environmental applications, such as the detection and monitoring of pollutants or the development of new methods for water treatment and purification. Its unique chemical properties make it a promising candidate for the selective detection of specific contaminants or the removal of harmful substances from water.
5. Used in Research and Development:
Due to its unique structure and properties, 4-Fluoro-1,3-benzenediol is a valuable compound for research and development purposes. It can be used as a model compound to study various chemical reactions, mechanisms, and processes, contributing to the advancement of scientific knowledge in the field of organic chemistry.

InChI:InChI=1/C12H4F8N2/c13-3-1(4(14)8(18)11(21)7(3)17)2-5(15)9(19)12(22)10(20)6(2)16/h21-22H2

Upstream product

• 140681-55-6 Selectfluor 
• 108-46-3 recorcinol 
• 89-86-1 4-hydroxysalicylic acid 
• 151-10-0 1,3-Dimethoxybenzene 
• 2040-04-2 2,6-dimethoxyacetophenone 
• 699-83-2 2,6-dihydroxylacetophenone 
• 195136-62-0 1-Fluoro-2,4-dimethoxy-5-nitro-benzene 
• 195136-65-3 1-Amino-2,4-dimethoxy-5-fluorobenzene 
• 2105-61-5 1,2,4-trifluoro-5-nitrobenzene 
• 117902-11-1 2,6-dimethoxy-3-fluoroacetophenone 
• 17715-70-7 1,3-dimethoxy-4-fluorobenzene 

Downstream Products

• 913689-08-4 2-(2,7-difluoro-3,6-dihydroxy-9H-xanthen-9-yl)benzoic acid 
• 781666-16-8 3-(2,7-difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)-9,10-diphenyl-anthracene-2-carboxylic acid 
• 443302-14-5 C₃₆H₃₀F₂N₂O₁₁S 
• 443302-16-7 C₃₆H₃₀F₂N₂O₁₁S 
• 825628-77-1 1-(2,7-difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester 
• 448957-14-0 3-(allyloxy)-4-fluorophenyl-4-methylbenzenesulfonate 
• 879288-18-3 4-(2,7-difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)-3-methylbenzoic acid methyl ester 
• 879288-14-9 4-(2,7-difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)-3-methylbenzoic acid 
• 952053-74-6 1-{[4-(2,7-difluoro-6-hydroxy-3-oxo-xanthen-9-yl)-3-methylbenzoyl]oxy}pyrrolidine-2,5-dione 
• 404335-94-0 fluozin-3, trimethyl ester 
• 851128-57-9 6-nitroso-4-fluororesorcinol 
• 178374-98-6 6-fluoro-7-hydroxy-2,3-dihydro-4H-chromen-4-one 

Relevant academic research and scientific papers

Decarboxylative Fluorination of Arylcarboxylic Acids Promoted by ortho-Hydroxy and Amino Groups

A novel decarboxylative fluorination process has been developed for the synthesis of ortho-hydroxy/amino arylfluorides from salicylic acid analogs, in which the ortho-hydroxy/amino group plays an important role in the transformation. In addition, various arylfluorides are obtained in good to excellent yields under mild conditions.

8-FLUORO-4-ALKYLUMBELLIFERYL ALPHA-D-GLUCOPYRANOSIDE, BIOLOGICAL STERILIZATION INDICATOR INCLUDING THE SAME AND ITS USE IN A METHOD OF DETERMINING EFFICACY OF A STERILIZATION PROCESS

A self-contained biological sterilization indicator comprises: a housing; bacterial spores comprising, and/or capable of producing, an enzyme capable of catalyzing cleavage of an enzyme substrate; and a frangible container containing a composition, wherein the composition comprises the enzyme substrate, wherein if the frangible container is broken the composition will contact the bacterial spores to form a mixture having an initial pH in the range from 6.0 to 9.0. The enzyme substrate comprises a fluorinated 4'-alkylumbelliferyl α-D-glucopyranoside represented by the structural formula (I), wherein R is an alkyl group having from 1 to 12 carbon atoms. A biological sterilization indicator comprising a kit containing isolated components comprising (i) bacterial spores comprising, and/or capable of producing, an enzyme capable of catalyzing cleavage of the enzyme substrate and a method of assessing efficacy of a sterilization process are also disclosed.

FLUORINATED 4' ALKYLUMBELLIFERYL α-D-GLUCOPYRANOSIDES, BIOLOGICAL STERILIZATION INDICATORS INCLUDING THE SAME AND METHODS OF USING THE SAME

A self-contained biological sterilization indicator comprises: a housing; bacterial spores comprising, and/or capable of producing, an enzyme capable of catalyzing cleavage of an enzyme substrate; and a frangible container containing a composition, wherein the composition comprises the enzyme substrate, wherein if the frangible container is broken the composition will contact the bacterial spores to form a mixture having an initial pH in the range from 6.0 to 9.0. The enzyme substrate comprises a fluorinated 4'-alkylumbelliferyl α-D-glucopyranoside represented by the structural formula (I) wherein one of R1 and R2 is F and the other is H, and R3 is an alkyl group having from 1 to 12 carbon atoms. A biological sterilization indicator comprising a kit containing isolated components comprising (i) bacterial spores comprising, and/or capable of producing, an enzyme capable of catalyzing cleavage of the enzyme substrate and a method of assessing efficacy of a sterilization process are also disclosed.

Promotional effect of ionic liquids in the electrophilic fluorination of phenols

The influence of a stoichiometric amount of ionic liquids (IL) on the fluorination of phenols in various solvents has been studied. The fluorination of phenol, 1-naphthol and resorcinol was carried out using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4, Selectfluor) with the formation of 2-fluoro-, 4-fluorophenol, 2-fluoro-, 4-fluoronaphthol and 4-fluoro-, 4,6-difluoro-benzene-1,3-diol as the main products. The use of a stoichiometric amount of ionic liquid as an additive results in acceleration of the reactions. The effect is most significant at low temperatures. It has been found that solvent polarity has an essential effect on the difference in yields of fluoroproducts obtained in the presence of IL and without it.

Fluorination of aromatic compounds with N-fluorobenzenesulfonimide under solvent-free conditions

Reactions of N-fluorobenzenesulfonimide with methylbenzenes, phenols, and phenol ethers were studied under solvent-free conditions. The rate constant ratio for the reactions with mesitylene and durene indicates polar mechanism of the process. Solvent-free fluorination of aromatic compounds with N-fluorobenzenesulfonimide in some cases is more selective than reactions with other N-F reagents in a solvent.

Antidiabetic activity of passive nonsteroidal glucocorticoid receptor modulators

Much has been learned about the consequences of glucocorticoid receptor antagonism by studying steroidal active antagonists such as RU-38486 (1). In the liver glucocorticoid receptor antagonism suppresses hepatic glucose production decreasing plasma glucose levels; however, extrahepatic antagonism produces several undesirable side effects including activation of the hypothalamic pituitary adrenal axis. A series of nonsteroidal passive N-(3-dibenzylamino-2- alkyl-phenyl)-methanesulfonamide glucocorticoid receptor modulators was discovered. Liver selective and systemically available members of this series were found and characterized in diabetes and side effect rodent models. A highly liver selective member of this series, acid 14, shows efficacy in the ob/ob model of diabetes. It lowers plasma glucose, cholesterol, and free fatty acid concentrations and reduces the rate of body weight gain. The structurally related systemically available passive modulator 12 lowers glucose, HbA 1c, triglyceride, free fatty acid, and cholesterol levels. Interestingly, it did not acutely activate the hypothalamic pituitary adrenal axis in unstressed CD-1 mice or have the abortive effects observed with 1. These results indicate that passive GR antagonists may have utility as antidiabetic agents.

GLUCOCORTICOID RECEPTOR MODULATORS

Compounds of formula (I) or pharmaceutically acceptable salts thereof are novel glucocorticoid receptor modulators and are useful for treating type II diabetes in a mammal.

Fluorinated xanthene derivatives

The family of dyes of the invention are fluoresceins and rhodols that are directly substituted on one or more aromatic carbons by fluorine. These fluorine-substituted fluorescent dyes possess greater photostability and have lower sensitivity to pH changes in the physiological range of 6-8 than do non-fluorinated dyes, exhibit less quenching when conjugated to a substance, and possess additional advantages. The dyes of the invention are useful as detectable tracers and for preparing conjugates of organic and inorganic substances.

Synthesis, Properties, and Reactivity of N,N'-Difluorobipyridinium and Related Salts and Their Applications as Reactive and Easy-To-Handle Electrophilic Fluorinating Agents with High Effective Fluorine Content

N,N′-Difluoro-2,2′-, -2,4′-, -3,3′-, -4,4′-bipyridinium and substituted N,N′-difluoro-2,2′-bipyridinmm bis(triflates), bis(tetrafluoroborates), bis(hexafluorophosphates), and bis(hexafluoroantimonates) 1-9 were synthesized in high yields by the direct fluorination of a mixture of a bipyridyl and a Lewis acid, a Br?nsted acid, or the alkali metal salt of an acid. The higher homologues, trimer 10 and polymer 11, were also synthesized. Unsubstituted or electron-donating group-substituted N,N′- difluorobipyridinium salts are stable nonhygroscopic crystals, while the electron-withdrawing group- substituted N,N′-diflurobipyridinium salts 3, 5, and 6 are moisture-sensitive crystals. Hydrolysis of 1b in boiling water gave 3,3′-dihydroxy-2,2′-bipyridyl. The reactivity determination indicated that the fluorinating capability decreased in the order 2,2′- ? 2,4' > 3,3′- ≈ 4,4′-isomer ? N-fluoropyridinium salt and that the two N-F moieties in a molecule were effective for fluorination. This fluorination occurred in a step-by-step manner, and the reactivity difference between the first and second fluorinations was very small. N,N′-Difluoro-2,2′-bipyridinium bis(tetrafluoroborate) (1b) is thus shown to be a highly reactive and easy-to-handle electrophilic fluorinating agent with the high effective fluorine content (103.3 g/kg) for preparing many fluoro organic compounds.

(3R,4S)-3-[4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl]chroman-4,7-diol: A conformationally restricted analogue of the NRr2B subtype-selective NMDA antagonist (1S,2S)-1-(4-hydroxyphenyl)-2(4-hydroxy-4-phenylpiperidino)-1- propanol

(1S,2S)-1-(4-Hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidino)-1-propanol (CP-101,606, 1)is a recently described antagonist of N-methyl-D-aspartate (NUDA) receptors containing the NR2B subunit. In the present study, the optimal orientation of compounds of this structural type for their receptor was explored. Tethering of the pendent methyl group of 1 to the phenolic aromatic ring via an oxygen atom prevents rotation about the central portion of the molecule. Several of the new chromanol compounds have high affinity for the racemic [3H]CP-101,606 binding site on the NUDA receptor and protect against glutamate toxicity in cultured hippocampal neurons. The new ring caused a change in the stereochemical preference of the receptor - cis (erythro) compounds had better affinity for the receptor than the trans isomers. Computational studies suggest that steric interactions between the pendent methyl group and the phenol ring in the acyclic series determine which structures can best fit the receptor. The chromanol analogue, (3R,4S)- 3-[4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl]chroman-4,7-diol (12a, CP- 283,097), was found to possess potency and selectivity comparable to CP- 101,606. Thus 12a is a new tool to explore the function of the NR2B- containing NUDA receptors.