195136-67-5

Usage

Uses

Used in Pharmaceutical Industry:
2,4-DiMethoxy-3,5-difluorobenzenaMine is used as a reagent for the preparation of highly potent acyl protein thioesterase inhibitors. These inhibitors have potential applications in the treatment of Huntington's disease, a neurodegenerative disorder that affects muscle coordination and cognitive abilities.
Additionally, 1,3-Dimethoxy-2,4-difluorobenzene, a related compound, is also used as a reagent in the preparation of these potent inhibitors, further highlighting the utility of these types of compounds in the development of therapeutic agents for neurological conditions.

Upstream product

• 67-56-1 methanol 
• 195136-63-1 1,3-difluoro-2,4-dimethoxy-5-nitrobenzene 
• 551-62-2 1,2,3,4-tetrafluorobenzene 
• 5580-79-0 2,3,4,5-tetrafluoro-1-nitrobenzene 

Downstream Products

• 195136-69-7 2,4-difluoro-1,3-dimethoxybenzene 
• 195136-71-1 2,4-difluorobenzene-1,3-diol 
• 209541-27-5 3,5-Difluoro-2,4-dihydroxybenzaldehyde 
• 215868-31-8 6,8-difluoro-7-hydroxycoumarin-3-carboxylic acid 
• 215868-23-8 6,8-difluoro-7-hydroxy-4-methyl-2H-chromen-2-one 
• 215868-26-1 6',8'-difluoro-4’-methylumbelliferyl α-D-glucopyranoside 
• 1581248-41-0 2′,4′,5′,7′-tetrafluoro-3′,6′-dihydroxy-5,10-diphenyl-3H-spiro-[anthra[2,3-c]furan-1,9′-xanthen]-3-one 
• 625119-45-1 1,3-difluoro-5-isocyanato-2,4-dimethoxybenzene 

Relevant academic research and scientific papers

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.

Palladium-Mediated Approach to Coumarin-Functionalized Amino Acids

Incorporation of the fluorogenic l-(7-hydroxycoumarin-4-yl)ethylglycine into proteins is a valuable biological tool. Coumarins are typically accessed via the Pechmann reaction, which requires acidic conditions and lacks substrate flexibility. A Pd-mediated coupling is described between o-methoxyboronic acids and a glutamic acid derived (Z)-vinyl triflate, forming latent coumarins. Global deprotection with BBr3 forms the coumarin scaffold in a single step. This mild and scalable route yielded five analogues, including a probe suitable for use at lower pH.

A Practical Synthesis of 6,8-Difluoro-7-hydroxycoumarin Derivatives for Fluorescence Applications

A practical synthesis for 6,8-difluoro-7-hydroxycoumarin-3-carboxylic acid - one of the most widely used coumarin fluorescence imaging dye for bioconjugation - is reported. The synthesis was optimized for a preparative scale to obtain 14 g of the fluoresc

Aarhus green: A tetrafluoro-substituted derivative of fluorescein

The synthesis and characterization of a 2′,4′,5′,7′-tetrafluorinated derivative of fluorescein, called Aarhus Green, is reported. As with related 2′,7′-difluorinated compounds, tetrafluorination of the xanthene-derived moiety makes the more fluorescent anion accessible over a larger pH range. However, in contrast to a published report, we find that fluorination in the 4′ and 5′ positions does not appreciably decrease the fluorescence quantum yield, φf. Rather, Aarhus Green has a reasonably large φf (0.79 ± 0.04). Moreover, Aarhus Green does not efficiently sensitize the production of singlet oxygen and it is photostable. Thus, tetrafluorination of the xanthene moiety in fluorescein derivatives can be a useful tool in the development of fluorescent probes.

Aarhus sensor green: A fluorescent probe for singlet oxygen

A tetrafluoro-substituted fluorescein derivative covalently linked to a 9,10-diphenyl anthracene moiety has been synthesized, and its photophysical properties have been characterized. This compound, denoted Aarhus Sensor Green (ASG), has distinct advantages for use as a fluorescent probe for singlet molecular oxygen, O2(a1δg). In the least, ASG overcomes several limitations inherent to the use of the related commercially available product called Singlet Oxygen Sensor Green (SOSG). The functional behavior of both ASG and SOSG derives from the fact that these weakly fluorescent compounds rapidly react with singlet oxygen via a π2 + π4 cycloaddition to irreversibly yield a highly fluorescent endoperoxide. The principal advantage of ASG over SOSG is that, at physiological pH values, both ASG and the ASG endoperoxide (ASG-EP) do not themselves photosensitize the production of singlet oxygen. As such, ASG better fits the requirement of being a benign probe. Although ASG readily enters a mammalian cell (i.e., HeLa) and responds to the presence of intracellular singlet oxygen, its behavior in this arguably complicated environment requires further investigation.

Development of highly potent inhibitors of the ras-targeting human acyl protein thioesterases based on substrate similarity design

A matter of common sense: A common recognition motif consisting of a negatively charged group five to six bonds away (red) from the (thio)ester functionality (green) and a positively charged tail group ten to twelve bonds away (blue) was identified in two

Positive allosteric modulators of the nicotinic acetylcholine receptor

The invention provides compounds of Formula I: These compounds may be in the form of pharmaceutical salts or compositions, may be in pure enantiomeric form or racemic mixtures, and are useful in pharmaceuticals used to treat diseases or conditions in which α7 nAChR is known to be involved.

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.

Derivatives of 6,8-difluoro-7-hydroxycoumarin

The present invention comprises 6,8-difluoro-7-hydroxycoumarins and derivatives of 6,8-difluoro-7-hydroxycoumarins, including reactive dyes, dye-conjugates and enzyme substrates. These fluorine-substituted fluorescent dyes typically possess greater photostability and lower pH sensitivity in the physiological pH range than their nonfluorinated analogs, exhibit less fluorescence quenching when conjugated to a substance, possess absorption and emission spectra that closely match those of their nonfluorinated analogs, and also exhibit higher quantum yields than their nonfluorinated analogs.

Synthesis of fluorinated fluoresceins

Several novel fluorinated fluoresceins (Oregon Green dyes) were prepared by the reaction of fluororesorcinols with phthalic anhydride and its derivatives. A novel regiospecific synthesis of fluororesorcinols was key to the successful synthesis of these new fluorophores. (Polyfluoro)- nitrobenzenes were reacted with 2 equiv of sodium methoxide followed by reduction, hydrodediazoniation, and demethylation, giving the first straightforward synthesis of 2-fluororesorcinol, 4-fluororesorcinol, 2,4- difluororesorcinol, and 2,4,5-trifluororesorcinol. These fluorinated fluoresceins have higher photostability and ionize at a lower pH (pK(a) = 3.3-6.1) than fluorescein (pK(a) = 6.5). Some of the fluorinated fluoresceins have very high quantum yields (0.85-0.97), which, in combination with their lower pK(a)s and high photostability, makes them superior fluorescent dyes for use as reporter molecules in biological systems.