455-91-4

Usage

Uses

Used in Pharmaceutical Industry:
3-Fluoro-4-methoxyacetophenone is used as a synthetic intermediate for the production of chalcones, which are important compounds in the pharmaceutical industry. Chalcones have been found to possess a wide range of biological activities, including anti-inflammatory, antioxidant, and anticancer properties. The unique structure of 3-Fluoro-4-methoxyacetophenone allows for the creation of novel chalcone derivatives with potential therapeutic applications.
Used in Chemical Synthesis:
3-Fluoro-4-methoxyacetophenone serves as a valuable building block in the synthesis of various organic compounds. Its fluorinated and methoxylated structure can be further modified through various chemical reactions, enabling the development of new molecules with diverse properties and applications. This versatility makes it an important compound in the field of organic chemistry and materials science.

InChI:InChI=1/C7H6FNO3/c1-12-7-3-2-5(9(10)11)4-6(7)8/h2-4H,1H3

Upstream product

• 321-28-8 1-fluoro-2-methoxybenzene 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 403-14-5 3-fluoro-4-hydroxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 29650-44-0 2-fluorophenyl acetate 
• 367-12-4 2-fluorophenol 
• 74-88-4 methyl iodide 

Downstream Products

• 403-14-5 3-fluoro-4-hydroxyacetophenone 
• 403-20-3 3-fluoro-p-anisic acid 
• 350-27-6 2-bromo-1-(3-fluoro-4-methoxyphenyl)ethanone 
• 442-43-3 6-bromo-2-(3-fluoro-4-methoxy-phenyl)-quinoline-4-carboxylic acid 
• 347-09-1 2-(3'-fluoro-4'-methoxyphenyl)-1H-indole 
• 70862-63-4 4,4,4-trifluoro-1-(3-fluoro-4-methoxyphenyl) butane-1,3-dione 
• 81516-12-3 4,4,5,5,5-pentafluoro-1-(3-fluoro-4-methoxyphenyl) pentane-1,3-dione 
• 170570-77-1 4,4-difluoro-1-(3-fluoro-4-methoxyohenyl)-butane-1,3-dione 
• 195708-39-5 ethyl (3-fluoro-4-methoxybenzoyl)acetate 
• 185211-24-9 methyl 3-(3-fluoro-4-methoxyphenyl)-3-oxopropanoate 
• 801233-53-4 4-chloro-2-(3-fluoro-4-methoxyphenyl)-6-methoxyquinoline 
• 801233-45-4 2-(3-fluoro-4-methoxyphenyl)-6-methoxyquinolin-4-ol 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of novel dual PPARα/δ agonists for the treatment of T2DM

Dual PPARα/δ agonists have been considered as potential therapeutics for the treatment of type 2 diabetes mellitus. After comprehensive structure–activity relationship study based on GFT505, a novel dual PPARα/δ agonist compound 6 was identified with highly activities on PPARα/δ and higher selectivity against PPARγ than that of GFT505. The modeling study revealed that compound 6 binds well to the binding pockets of PPARα and PPARδ, which formed multiple hydrogen bonds with key residues related to the activation of PPARα and PPARδ. Moreover, oral glucose tolerance test exhibited that compound 6 exerts dose-dependent anti-diabetic effects in ob/ob mice and reveals similar potency to that of GFT505, the most advanced candidate in this field. These findings suggested that compound 6 is a promising candidate for further researches, and the extended chemical space might help us to explore better PPARα/δ agonist.

Preparation method of Deracoxib

The invention discloses a preparation method of Deracoxib, and belongs to the field of Deracoxib preparation. The preparation method of Deracoxib disclosed by the invention comprises the following steps: (1) taking methane chloride as a reaction solvent, and reacting 2-fluoroanisole with acetylchloride under the effect of acid so as to obtain 3-fluoro-4-methoxyacetophenone; (2) taking methane chloride as a reaction solvent, and reacting 3-fluoro-4-methoxyacetophenone with ethyl difluoroacetate under the effect of alkaline so as to obtain 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)-1,3-butanedione; and (3) under the existence of an ethyl alcohol solvent, reacting 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)-1,3-butanedione with para-sulfamine phenylhydrazine or salt thereof so as to obtain Deracoxib. According to the preparation method of Deracoxib disclosed by the invention, dichloromethane is used as a solvent, the toxicity of the solvent is low, the cost of the solvent is lower than thatof methyl tertiary butyl ether, and the production cost is obviously reduced on the premise of guaranteeing the yield.

Fries rearrangement: Scalable synthesis of key fluoro building blocks 3-fluoro-4-methoxybenzoyl chloride and 1,2-diethoxy-3-fluorobenzene

Lewis acid catalyzed Fries rearrangement of 2-fluorophenyl acetate (3) was performed on kg scale. The ortho 5 and para 4 isomers obtained were separated in an industrially feasible way. Compound 4 was then converted into fluorinated building block 3-fluoro-4-methoxybenzoyl chloride (1) while compound 5 was converted into 1,2-diethoxy-3-fluorobenzene (2) in high yields.

Transformations of organic molecules with F-TEDA-BF4 in ionic liquid media

The transformations of organic molecules with F-TEDA-BF4 (1) were investigated in the hydrophilic ionic liquid (IL) 1-butyl-3-methyl- imidazolium tetrafluoroborate ([bmim][BF4], 2) and the hydrophobic IL 1-butyl-3-methyl-imidazolium hexafluorophosphate ([bmim][PF6], 3). The range of substrates included alkyl substituted phenols 4a-c, 9, 13, 1,1-diphenylethene (15), alkyl aryl ketones 19-22, aldehydes 23-25 and methoxy-substituted benzene derivatives 26-30. The evaluation of the outcome of reactions performed in IL media in comparison to those of the corresponding reactions in conventional organic solvents revealed that the transformations in IL are less efficient and selective. The effect of the presence of a nucleophile (MeOH, H2O, MeCN) on the course of reaction was also studied.

PHARMACEUTICAL COMPOUNDS

The invention provides a compound of the formula (I) or a salt, solvate, tautomer or N-oxide thereof; wherein A is a saturated hydrocarbon linker group; E is a monocyclic or bicyclic carbocyclic or heterocyclic group; L1 is a bond or a linker selected from C1-C4 alkenylene, C1-C4 alkynylene, -CONR’, -NR’CO, -S, -C(O)-, -C(NR11)-, -C(S)-, -N(R11)2, C(=CHR11), -SO- and -SO2-; or L1 together with t R16 forms and 8-12 membered fused bicyclic heteroaryl ring system; L3 is a bond or a linker selected from CONH and HNCO; provided that L1 and L3 cannot both be linkers simultaneously; and provided also that L1 and L3 cannot both be a bond simultaneously; R16 is an optionally substituted 5- to 12-membered monocyclic or bicyclic carbocyclic or heterocyclic ring; L2 is absent or is a linker selected from C]-C4 alkylene, Ci-C4 alkenylene, Ci-C4 alkynylene, -CONR’-, -NR’CO-, -O-, -S-, -C(O)-, C(=CHR11), C(S)-, -N(R11)2, C3-4 cycloalkanediyl, -SO- and -SO2-; R17 is absent or is C1-6 alkyl or an optionally substituted 5 to 12 membered carbocyclic or heterocyclic ring; provided that when R17 is absent, then L2 is also absent; and R2, R3, R4, R5, R11 and R’ are as defined in the claims.

Treatment of inflammation and inflammation-related disorders with a combination of a cyclooxygenase-2 inhibitors and a leukotriene B4 receptor antagonist

Combinations of a cyclooxygenase-2 inhibitor and a leukotriene B4receptor antagonist are described for treatment of inflammation and inflammation-related disorders.

Immunosuppressive effects of administration of a cyclooxygenase-2 inhibitor and a 5-lipoxygenase inhibitor

A method to suppress immune, acute or delayed-type hypersensitivity by treatment with a combination of a therapeutically-effective amount of a 5-lipoxygenase inhibitor and a cyclooxygenase-2 inhibitor is reported. The method may be used, for example, to suppress the immune response associated with organ transplantation, graft versus host disease, and conditions with underlying autoimmune or inflammatory reactivities or responses.

Immunosuppressive effects of administration of a cyclooxygenase-2 inhibitor and a leukotriene A4 hydrolase inhibitor

Treatment with a cyclooxygenase-2 inhibitor and a leukotriene A4hydrolase inhibitor is described as being useful in reducing recipient rejection of transplanted organs and for treatment of autoimmnune diseases.

IMMUNOSUPPRESSIVE EFFECTS OF ADMINISTRATION OF A CYCLOOXYGENASE-2 INHIBITOR AND A LEUKOTRIENE B4 RECEPTOR ANTAGONIST

Treatment with a cyclooxygenase-2 inhibitor and a leukotriene B 4 receptor antagonist is described as being useful in reducing recipient rejection of transplanted organs and for treatment of autoimmune diseases.

Solvent directing immediate fluorination of aromatic ketones using 1- fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

Reactions of aryl alkyl ketones with 1-fluoro-4-hydroxy1,4- diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Accufluor(TM) NFTh) in methanol result in selective and almost quantitative formation of the corresponding α-fluoroketones, while in acetonitrile exclusive fluorofunctionalisation of the activated aromatic ring take place.