455-91-4

Basic information

• Product Name: 3-Fluoro-4-methoxyacetophenone
• Synonyms: BUTTPARK 153\33-60;3'-FLUORO-4'-METHOXYACETOPHENONE;3'-FLUORO-4-METHOXYACETOPHENONE;3-FLUORO-4-METHOXYACETOPHENONE;1-(3-FLUORO-4-METHOXY-PHENYL)-ETHANONE;1-(3-FLUORO-4-METHOXYPHENYL)-1-ETHANONE;3’-Fluoro-4’-methyoxyacetophenone;Ethanone, 1-(3-fluoro-4-methoxyphenyl)-
• CAS NO: 455-91-4
• Molecular Formula: C₉H₉FO₂
• Molecular Weight: 168.16
• EINECS: 207-253-8
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);ketone;Adehydes, Acetals & Ketones;Anisoles, Alkyloxy Compounds & Phenylacetates;Fluorine Compounds;C9;Carbonyl Compounds;Ketones;Fluorine series
• Mol File: 455-91-4.mol
• Article Data: 21

Chemical Properties

• Melting Point: 92-94 °C(lit.)
• Boiling Point: 147-148 °C20 mm Hg(lit.)
• Flash Point: 147-148°C/20mm
• Appearance: white to light yellow crystal powder
• Density: 1.1410 (estimate)
• Vapor Pressure: 0.00775mmHg at 25°C
• Refractive Index: 1.521
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 2084062
• CAS DataBase Reference: 3-Fluoro-4-methoxyacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluoro-4-methoxyacetophenone(455-91-4)
• EPA Substance Registry System: 3-Fluoro-4-methoxyacetophenone(455-91-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 455-91-4(Hazardous Substances Data)

Usage

Uses

3’-Fluoro-4’methoxyacetophenone is used in the synthesis chalcones,

General Description

3′-Fluoro-4′-methoxyacetophenone can be prepared by Friedel-Crafts reaction of o-fluoroanisole with acetic anhydride.

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 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 74-88-4 methyl iodide 
• 367-12-4 2-fluorophenol 
• 29650-44-0 2-fluorophenyl acetate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 442-44-4 2-(3-fluoro-4-methoxy-phenyl)-6-methyl-quinoline-4-carboxylic acid 
• 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 
• 81516-12-3 4,4,5,5,5-pentafluoro-1-(3-fluoro-4-methoxyphenyl) pentane-1,3-dione 
• 81593-27-3 1-methoxy-2-fluoro-4-glyoxyloylbenzene 
• 1072710-25-8 3'-fluoro-4'-methoxyacetophenone O-4-nitrobenzyloxime 
• 1072710-23-6 3'-fluoro-4'-methoxyacetophenone O-3,4-difluorobenzyloxime 
• 1072710-24-7 3'-fluoro-4'-methoxyacetophenone-O-[(benzo[c][1,2,5]oxadiazol-5-yl)methyl]oxime 
• 1072710-26-9 3'-fluoro-4'-methoxyacetophenone O-3-fluorobenzyloxime 
• 1189785-35-0 2-(3-fluoro-4-methoxyphenyl)-2-methyloxirane 
• 185211-24-9 methyl 3-(3-fluoro-4-methoxyphenyl)-3-oxopropanoate 

Relevant articles and documents

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.

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.

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.