136897-64-8

Basic information

• Product Name: 2,4,5-Trifluoro-3-methoxy-benzoic acid methyl ester
• Synonyms: METHYL 3-METHOXY-2,4,5-TRIFLUOROBENZOATE;2,4,5-TRIFLUORO-3-METHOXYBENZOIC ACID METHYL ESTER;2,4,5-TRIFLUORO-M-ANISIC ACID;Methyl 2,4,5-Trifluoro-3-Methoxy Benzoate;Benzoic acid, 2,4,5-trifluoro-3-Methoxy-, Methyl ester
• CAS NO: 136897-64-8
• Molecular Formula: C₉H₇F₃O₃
• Molecular Weight: 206.12
• Mol File: 136897-64-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 105-112 °C(lit.)
• Boiling Point: 262°C
• Flash Point: 109°C
• Appearance: white crystal powder
• Density: 1.342
• Vapor Pressure: 0.011mmHg at 25°C
• Refractive Index: 1.457
• CAS DataBase Reference: 2,4,5-Trifluoro-3-methoxy-benzoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,5-Trifluoro-3-methoxy-benzoic acid methyl ester(136897-64-8)
• EPA Substance Registry System: 2,4,5-Trifluoro-3-methoxy-benzoic acid methyl ester(136897-64-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 136897-64-8(Hazardous Substances Data)

Usage

General Description

2,4,5-Trifluoro-3-methoxy-benzoic acid methyl ester is a fluorinated aromatic compound with a molecular formula C9H6F3O3. It is a methyl ester derivative of 2,4,5-trifluoro-3-methoxybenzoic acid and is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals. This chemical is known for its strong electron-withdrawing properties due to the three fluorine atoms attached to the benzene ring, which makes it a valuable intermediate in organic synthesis. It is also used as a reagent in the production of specialty chemicals and has potential applications in the development of new drugs and crop protection products.

InChI:InChI=1/C9H7F3O3/c1-14-8-6(11)4(9(13)15-2)3-5(10)7(8)12/h3H,1-2H3

Upstream product

• 116751-24-7 2,4,5-trifluoro-3-hydroxybenzoic acid 
• 74-88-4 methyl iodide 
• 28749-88-4 3,4,6-trifluoro-5-hydroxyphthalic acid 

Downstream Products

• 137234-92-5 2,4,5-trifluoro-3-hydroxybenzoic acid methyl ester 
• 146981-08-0 5-amino-1-cyclopropyl-6-fluoro-8-methoxy-7-<(3-aminomethyl)-3-methyl-1-pyrrolidinyl>-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 
• 112811-71-9 ethyl 8-methoxy-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate 
• 122375-85-3 ethyl 3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate 
• 146981-09-1 5-amino-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid 

Relevant articles and documents

A prodrug approach toward the development of water soluble fluoroquinolones and structure-activity relationships of quinoline-3-carboxylic acids

A fluoroquinolone prodrug, PA2808, was prepared and shown to convert to the highly active parent drug PA2789. In vitro and in vivo activation of PA2808 by alkaline phosphatase was demonstrated using disk diffusion and rat lung infection models. The water solubility of PA2808 showed a marked increase compared to PA2789 over a pH range suitable for aerosol drug delivery. A total of 48 analogues based on PA2789 were prepared and screened against a panel of Gram-positive and Gram-negative pathogens. Incorporating a cyclopropane-fused pyrrolidine (amine g) at C-7 resulted in some of the most active analogues.

The Synthesis, Structure-Activity, and Structure-Side Effect Relationships of a Series of 8-Alkoxy- and 5-Amino-8-alkoxyquinolone Antibacterial Agents

A series of 1-cyclopropyl-6-fluoro-8-alkoxy (8-methoxy and 8-ethoxy)-quinoline-3-carboxylic acids and 1-cyclopropyl-5-amino-6-fluoro-8-alkoxyquinoline-3-carboxylic acids has been prepared and evaluated for antibacterial activity.In addition, they were also compared to quinolones with classic substitution at C8 (H, F, Cl) and the naphthyridine nucleus in a phototoxicity and mammalian cell cytotoxiciry assay.The series of 8-methoxyquinolones had antibacterial activity against Gram-positive, Gram-negative, and anaerobic bacteria equivalent to that most active 8-substituted compounds (8-F and 8-Cl).There was also a concomitant reduction in several of the potential side effects (i.e., phototoxicity and clonogenicity) compared to the most active quinolones with classic substitution at C-8.The 8-ethoxy derivatives had an even better safety profile but were significantly less active (2-3 dilutions) in the antibacterial assay.