79418-78-3

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Fluoro-4-hydroxy-5-methoxybenzaldehyde is used as a reagent in the synthesis of a series of caffeic acid phenethyl amide (CAPA) fluorinated derivatives. These derivatives have potential applications in the pharmaceutical industry, particularly for the development of new drugs with improved properties.
Used in Organic Chemistry:
3-Fluoro-4-hydroxy-5-methoxybenzaldehyde may be used to synthesize 3-(3-fluoro-4-hydroxy-5-methoxyphenyl)-N-phenethylacrylamide and 4-[(4-hydroxy-3-fluoro-5-methoxy-benzylidene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one. These synthesized compounds can be utilized in various applications, such as in the development of new materials or as intermediates in the synthesis of other organic compounds.
Used in Research and Development:
As an aryl fluorinated building block, 3-fluoro-4-hydroxy-5-methoxybenzaldehyde is valuable in research and development for the creation of new chemical entities and the exploration of novel chemical reactions. Its unique structure allows for the investigation of the effects of fluorination on the properties and reactivity of organic molecules.

InChI:InChI=1/C8H7FO3/c1-12-7-3-5(4-10)2-6(9)8(7)11/h2-4,11H,1H3

Upstream product

• 71144-35-9 3-fluoro-4,5-dihydroxybenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 100-97-0 hexamethylenetetramine 
• 456-49-5 1-fluoro-3-methoxybenzene 
• 127685-76-1 1-fluoro-2-hydroxy-3-methoxy-5-methylbenzene 
• 1089186-95-7 1-(3-fluoro-4-hydroxy-5-methoxyphenyl)-N,N,N-trimethylmethanaminium iodide 
• 73943-41-6 2-fluoro-6-methoxyphenol 
• 76-05-1 trifluoroacetic acid 
• 50-00-0 formaldehyd 
• 103905-49-3 5-<(dimethylamino)methyl>-1-fluoro-2-hydroxy-3-methoxybenzene 
• 71144-41-7 (+/-)-5-Fluoronorepinephrine 

Downstream Products

• 127035-71-6 2-Fluoro-6-methoxy-4-((E)-2-thiophen-2-yl-vinyl)-phenol 
• 1256778-02-5 2-fluoro-4-formyl-6-methoxyphenyl trifluoromethanesulfonate 
• 1268364-24-4 C₁₀H₁₁FO₄ 
• 773870-27-2 3-fluoro-4-hydroxy-5-methoxybenzoic acid 
• 1338707-78-0 C₈H₇FO₄ 
• 1338707-79-1 C₂₄H₂₃FO₆ 
• 1338707-80-4 C₂₃H₂₁FO₆ 
• 1338707-94-0 C₃₁H₂₉FN₂O₅ 
• 1470111-21-7 C₄₂H₅₁FO₁₀Si 
• 1470111-29-5 C₃₆H₃₇FO₁₀ 
• 1470110-64-5 formic acid 4-(tert-butyldimethylsilanyloxy)-3-fluoro-5-methoxyphenyl ester 
• 1470110-70-3 4-(tert-butyldimethylsilanyloxy)-3-fluoro-5-methoxyphenol 
• 1567848-25-2 2-[1-(3-fluoro-4-hydroxy-5-methoxy-phenyl)-meth-(Z)-ylidene]-6-o-tolyl-imidazo[2,1-b]thiazol-3-one 
• 773874-64-9 methyl 3-fluoro-4-hydroxy-5-methoxybenzoate 

Relevant academic research and scientific papers

cGAS ANTAGONIST COMPOUNDS

Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.

Efficient Co(OAc)2-catalyzed aerobic oxidation of EWG-substituted 4-cresols to access 4-hydroxybenzaldehydes

We reported an efficient ligand-free Co(OAc)2·4H 2O/NaOH/O2/ethylene glycol reaction system that enables selective aerobic oxidation of a wide range of substrates covering 2,6-di-EWG-, 2,3,6-tri-EWG-, 2-EWG-, and 2-EWG-6-EDG-substituted 4-cresols into the corresponding 4-hydroxybenzaldehydes. Based on the experimental investigations and well-defined p-benzoquinone methides, a plausible reaction mechanism was proposed. Considering the simplicity of the procedure and importance of the products, the methodology was expected to become a favorable and practical tool in related benzylic C(sp3)-H functionalization chemistry.

A highly efficient approach to vanillin starting from 4-cresol

A highly efficient approach to the famous flavor and fragrance compound vanillin has been developed starting from 4-cresol with the attention focused on improving the sustainability of all the reactions. The approach involves a three-step sequence of the quasi-quantitative selective clean oxybromination of 4-cresol, the high-yield selective aerobic oxidation of 2-bromo-4-cresol, and the quantitative methoxylation of 3-bromo-4-hydroxybenzaldehyde with the recovery of pure methanol. Herein, the pivotal oxidation and methoxylation reactions are logically investigated and developed into two concise methodologies. As a green alternative, the approach holds significant value for the sustainable manufacturing of vanillin. the Partner Organisations 2014.

Cu(OAc)2-catalyzed remote benzylic C(sp3)-H oxyfunctionalization for C=O formation directed by the hindered para-hydroxyl group with ambient air as the terminal oxidant under ligand- and additive-free conditions

A hindered para-hydroxyl group-directed remote benzylic C(sp3)-H oxyfunctionalization has been developed for the straightforward transformation of 2,6-disubstituted 4-cresols, 4-alkylphenols, 4-hydroxybenzyl alcohols and 4-hydroxybenzyl alkyl ethers into various aromatic carbonyl compounds. The ligand- and additive-free Cu(OAc)2-catalyzed atmospheric oxidation mediated by ethylene glycol unlocks a facile, atom-economical, and environmentally benign C=O formation for the functionalization of primary and secondary benzyl groups. Due to the pharmaceutical importance of 4-hydroxybenzaldehydes and 4-hydroxyphenones, the methodology is expected to be of significant value for both fundamental research and practical applications.

Chemoselective zinc/HCl reduction of halogenated β-nitrostyrenes: Synthesis of halogenated dopamine analogues

A detailed account regarding the synthesis of 2- and 5-halogenated dopamine is given. The key step is a chemoselective reduction of a nitrostyrene by Zn/HCl at 0 °C. These conditions represent a simple, low-cost alternative to reduction by water-sensitive hydride donors and two-step procedures. Under these conditions, aryl fluoride, chloride, and bromide groups are stable. However, iodine undergoes significant reductive dehalogenation.

CEPHEM COMPOUND HAVING CATECHOL GROUP

A compound of the formula: wherein X is -N=, -CH=, or the like; W is -CH2- or the like; U is -S- or the like; R1 and R2 are each independently hydrogen, halogen, optionally substituted lower alkyl, or the like; R3/su

The carbonate analogues of 5′-halogenated resiniferatoxin as TRPV1 ligands

A series of carbonate analogues of 5′-halogenated RTX have been investigated in order to examine the effect of the carbonate group as a linker and the role of halogens in the reversal of activity from agonism to antagonism for rat and human TRPV1 heterologously expressed in Chinese hamster ovary cells. The carbonate analogues showed similar activities to the corresponding RTX derivatives in rat TRPV1 but lower potency in human TRPV1. 5-Halogenation converted the agonists to partial agonists or full antagonists and the extent of antagonism reflected the order of I > Br > Cl > F, with a somewhat greater extent of antagonism for the derivatives of the 4-amino RTX surrogates compared to the corresponding derivatives of RTX itself. The carbonate analogues of I-RTX (60) and 5-bromo-4-amino-RTX (66) were potent and full antagonists with Ki(ant) = 2.23 and 2.46 nM, respectively, for rat TRPV1, which were ca. 5-fold more potent than I-RTX (2) under our conditions. The conformational analysis of the I-RTX-carbonate (60) indicated that its bent conformation was similar to that of I-RTX, consistent with compound 60 and I-RTX showing comparable potent antagonism.

Receptor activity and conformational analysis of 5′-halogenated resiniferatoxin analogs as TRPV1 ligands

A series of 5′-halogenated resiniferatoxin analogs have been investigated in order to examine the effect of halogenation in the A-region on their binding and the functional pattern of agonism/antagonism for rat TRPV1 heterologously expressed in Chinese hamster ovary cells. Halogenation at the 5-position in the A-region of RTX and of 4-amino RTX shifted the agonism of parent compounds toward antagonism. The extent of antagonism was greater as the size of the halogen increased (I > Br > Cl > F) while the binding affinities were similar, as previously observed for our potent agonists. In this series, 5-bromo-4-amino RTX (39) showed very potent antagonism with K i (ant) = 2.81 nM, which was thus 4.5-fold more potent than 5′-iodo RTX, previously reported as a potent TRPV1 antagonist. Molecular modeling analyses with selected agonists and the corresponding halogenated antagonists revealed a striking conformational difference. The 3-methoxy of the A-region in the agonists remained free to interact with the receptor whereas in the case of the antagonists, the compounds assumed a bent conformation, permitting the 3-methoxy to instead form an internal hydrogen bond with the C4-hydroxyl of the diterpene.