74733-29-2

Basic information

• Product Name: methyl 2-fluoro-4-methylbenzoate
• Synonyms: methyl 2-fluoro-4-methylbenzoate;2-Fluoro-4-Methyl-benzoic acid Methyl ester
• CAS NO: 74733-29-2
• Molecular Formula: C₉H₉FO₂
• Molecular Weight: 168.1649632
• Mol File: 74733-29-2.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 226.825°C at 760 mmHg
• Flash Point: 88.537°C
• Appearance: /
• Density: 1.138g/cm³
• Vapor Pressure: 0.08mmHg at 25°C
• Refractive Index: 1.491
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: methyl 2-fluoro-4-methylbenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-fluoro-4-methylbenzoate(74733-29-2)
• EPA Substance Registry System: methyl 2-fluoro-4-methylbenzoate(74733-29-2)

Safety Data

• Hazardous Substances Data: 74733-29-2(Hazardous Substances Data)

Usage

General Description

Methyl 2-fluoro-4-methylbenzoate is a chemical compound with the molecular formula C9H9FO2. It is a fluoro-substituted ester of benzoic acid, containing a methyl and fluoro group on the benzene ring. methyl 2-fluoro-4-methylbenzoate is commonly used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and organic compounds. It is also used as a flavoring agent in the food industry and as a fragrance ingredient in the cosmetic industry. Methyl 2-fluoro-4-methylbenzoate is known for its wide range of applications in different fields, making it an important chemical compound in research and industrial processes.

InChI:InChI=1/C9H9FO2/c1-6-3-4-7(8(10)5-6)9(11)12-2/h3-5H,1-2H3

Upstream product

• 67-56-1 methanol 
• 7697-23-6 2-fluoro-4-methylbenzoic Acid 
• 59189-98-9 2-fluoro-4-methylbenzoyl chloride 
• 74-88-4 methyl iodide 
• 452-74-4 4-bromo-3-fluorotoluene 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 452-79-9 2‐fluoro‐1‐iodo‐4‐methylbenzene 

Downstream Products

• 85070-57-1 methyl 4-(bromomethyl)-2-fluoro-benzoate 
• 74733-25-8 methyl 3-fluoro-4-formylbenzoate 
• 85070-58-2 methyl 2-fluoro-4-formylbenzoate 
• 1382991-41-4 methyl 2-fluoro-4-(3-fluorobenzyl)benzoate 
• 1382991-42-5 2-fluoro-4-(3-fluorobenzyl)benzoic acid 
• 1190848-45-3 methyl 2-fluoro-4-((3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl)benzoate 
• 1190848-49-7 methyl 2-fluoro-4-(1-(1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalen-7-yl)vinyl)benzoate 
• 1190848-23-7 2-fluoro-4-(1-(1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalen-7-yl)vinyl)benzoic acid 
• 161796-11-8 3-fluoro-terephthalic acid 4-methyl ester 
• 1190848-41-9 methyl 4-(chlorocarbonyl)-2-fluorobenzoate 
• 1283718-57-9 methyl 2-fluoro-4-(hydroxymethyl)benzoate 
• 1072438-53-9 methyl 4-(aminomethyl)-2-fluorobenzoate hydrochloride 
• 753924-48-0 2-fluoro-4-methyl-5-nitrobenzoic acid methyl ester 

Relevant articles and documents

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.

A Dual Modulator of Farnesoid X Receptor and Soluble Epoxide Hydrolase to Counter Nonalcoholic Steatohepatitis

Nonalcoholic steatohepatitis arising from Western diet and lifestyle is characterized by accumulation of fat in liver causing inflammation and fibrosis. It evolves as serious health burden with alarming incidence, but there is no satisfying pharmacological therapy to date. Considering the disease's multifactorial nature, modulation of multiple targets might provide superior therapeutic efficacy. In particular, farnesoid X receptor (FXR) activation that revealed antisteatotic and antifibrotic effects in clinical trials combined with inhibition of soluble epoxide hydrolase (sEH) as anti-inflammatory strategy promises synergies. To exploit this dual concept, we developed agents exerting partial FXR agonism and sEH inhibitory activity. Merging known pharmacophores and systematic exploration of the structure-activity relationship on both targets produced dual modulators with low nanomolar potency. Extensive in vitro characterization confirmed high dual efficacy in cellular context combined with low toxicity, and pilot in vivo data revealed favorable pharmacokinetics as well as engagement on both targets in vivo.

Synthesis of a new fluorine-18-labeled bexarotene analogue for PET imaging of retinoid X receptor

The reference standard 2-fluoro-4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8- tetrahydronaphthalen-2-yl)vinyl)benzoic acid was synthesized from 2,5-dimethyl-2,5-hexanediol and 2-fluoro-4-methylbenzoic acid in 10 steps with 3% overall chemical yield. The precursor 2-nitro-4-(1-(3,5,5,8,8-pentamethyl-5, 6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic acid was synthesized from 2,5-dimethyl-2,5-hexanediol and dimethyl-2-nitroterephthalate in seven steps with 2% overall chemical yield. The target tracer 2-[18F]fluoro-4-(1- (3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic acid was synthesized from its nitro-precursor by the nucleophilic substitution with K[18F]F/Kryptofix 2.2.2 and isolated by HPLC combined with solid-phase extraction (SPE) purification in 20-30% radiochemical yield with 37-370 GBq/μmol specific activity at end of bombardment (EOB).