369-25-5

Basic information

• Product Name: METHYL 3,4-DIFLUOROBENZOATE
• Synonyms: RARECHEM AL BF 0215;2,4-DIFLUOROBENZOIC ACID METHYL ESTER;BUTTPARK 89\07-66;METHYL 3,4-DIFLUOROBENZENECARBOXYLATE;METHYL 3,4-DIFLUOROBENZOATE;Methyl 3,4-difluorobenzoate 97%;Methyl3,4-difluorobenzoate97%;METHYL 3,4-DIFLUOROB
• CAS NO: 369-25-5
• Molecular Formula: C₈H₆F₂O₂
• Molecular Weight: 172.13
• Product Categories: Aromatic Esters;Acids & Esters;Fluorine Compounds;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 369-25-5.mol

Chemical Properties

• Melting Point: 23-27 °C(lit.)
• Boiling Point: 88 °C
• Flash Point: 184 °F
• Appearance: /
• Density: 1.268g/cm³
• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: 1.544
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: METHYL 3,4-DIFLUOROBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3,4-DIFLUOROBENZOATE(369-25-5)
• EPA Substance Registry System: METHYL 3,4-DIFLUOROBENZOATE(369-25-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41
• Safety Statements: 26-36/39
• WGK Germany: 3
• Hazardous Substances Data: 369-25-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 3,4-DIFLUOROBENZOATE is used as a key intermediate in the preparation of disubstituted 1,5-Naphthyridines, which serve as ALK5 inhibitors. ALK5, or Activin Receptor-like Kinase 5, is a receptor involved in various cellular processes, including cell proliferation and differentiation. Inhibiting ALK5 has therapeutic applications in treating conditions related to abnormal cell growth and differentiation.
Additionally, METHYL 3,4-DIFLUOROBENZOATE can be used in the development of novel drug delivery systems to enhance the bioavailability and therapeutic outcomes of ALK5 inhibitors, potentially improving the treatment of various diseases and conditions.

InChI:InChI=1/C8H8FNO2/c1-12-8(11)5-2-3-6(9)7(10)4-5/h2-4H,10H2,1H3

Upstream product

• 67-56-1 methanol 
• 455-86-7 3,4-Difluorobenzoic acid 
• 32137-19-2 1,2-difluoro-4-(trifluoromethyl)benzene 
• 328-84-7 1,2-dichloro-4-(trifluoromethyl)benzene 
• 367-11-3 ortho-difluorobenzene 
• 369-33-5 3',4'-difluoroacetophenone 
• 75-91-2 tert.-butylhydroperoxide 
• 34036-07-2 3,4 difluorobenzaldehyde 
• 124-38-9 carbon dioxide 

Downstream Products

• 570408-10-5 tert-butyl 4-(2-fluoro-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate 
• 1163247-87-7 4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-3-fluorobenzoic acid 
• 1345879-80-2 C₁₁H₁₁ClFNO₂ 
• 229957-07-7 3,4-difluorobenzohydrazide 
• 748183-87-1 Methyl 3-fluoro-4-(4-methylpiperidin-1-yl)benzoate 

Relevant articles and documents

Ruthenium-catalyzed hydrogenation of CO2as a route to methyl esters for use as biofuels or fine chemicals

A novel robust diphosphine-ruthenium(ii) complex has been developed that can efficiently catalyze both the hydrogenation of CO2 to methanol and its in situ condensation with carboxylic acids to form methyl esters; a TON of up to 3260 is achievable for the CO2 to methanol step. Both aromatic and aliphatic carboxylic acids can be transformed to their corresponding methyl esters with high conversion and selectivity (17 aliphatic and 18 aromatic examples). On the basis of a series of experiments, a mechanism has been proposed to account for the various steps involved in the catalytic pathway. More importantly, this approach provides a promising route for using CO2 as a C1 source for the production of biofuels, fine chemicals and methanol.

Copper-catalyzed oxidative methyl-esterification of 5-hydroxymethylfurfural using TBHP as an oxidizing and methylating reagent: A new approach for the synthesis of furan-2,5-dimethylcarboxylate

Catalytic conversion of 5-hydroxymethylfurfural (HMF) into furan-2,5-dimethylcarboxylate (FDMC) is of great significance in the production of polyethylene furanoate (PEF), a renewable biomass-derived polymer that can replace the fossil dependent polyethylene terephthalate (PET). Herein, for the first time, we report the synthesis of FDMC from oxidative methyl-esterification of HMF using tert-butyl hydroperoxide (TBHP) as an oxidizing and methylating reagent catalyzed by mesoporous alumina nanospheres-embedded with CuO nanoparticles (CuO/m-Al2O3). The CuO/m-Al2O3 catalysts with different copper contents were prepared by evaporation-induced self-assembly of a structure-directing agent (Pluronic P-123). The decomposition of P-123 during calcination in air results into the formation of a mesoporous structure with highly dispersed CuO nanoparticles. The as-prepared 6-CuO/m-Al2O3 exhibits excellent catalytic activity towards oxidative methyl-esterification of HMF into FDMC with 92% yield and turnover frequency (TOF) of 0.56 h?1. Furthermore, oxidative methyl-esterification of a range of substrates through SP3 C[sbnd]H bond functionalization has also been demonstrated using the same catalyst.

ALK5 INHIBITORS

The present disclosure provides inhibitors of activin receptor-like kinase 5 (ALK5). Also disclosed are methods to modulate the activity of ALK5 and methods of treatment of disorders mediated by ALK5.

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A series of new sulfone compounds containing the 1,3,4-oxadiazole moiety were designed and synthesized. Their structures were identified by 1H and 13C nuclear magnetic resonance and elemental analyses. Antibacterial bioassays indicated that most compounds exhibited promising in vitro antibacterial bioactivities against tobacco bacterial wilt at 200 μg/mL. The relationship between structure and antibacterial activity was also discussed. Among the title compounds, 5′c, 5′h, 5′i, and 5′j could inhibit mycelia growth of Ralstonia solanacearum in vitro by approximately 50% (EC50) at 39.8, 60.3, 47.9, and 32.1 μg/mL, respectively. Among them, compound 5′j was identified as the most promising candidate due to its stronger effect than that of Kocide 3000 [Cu(OH)2] within the same concentration range. Field trials demonstrated that the control effect of compound 5′j against tobacco bacterial wilt was better than that of the commercial bactericide Saisentong. For the first time, the present work demonstrated that sulfone derivatives containing 1,3,4-oxadiazole can be used to develop potential bactericides for plants.

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A series of 53 nitro derivatives rationally designed were obtained by parallel synthesis and screened against Leishmania donovani. Six compounds exhibited IC50 values lower than standard drugs. Brief SAR analysis revealed that substitution is important to the activity. Nitrothiophene analogues were more potent than the nitrofuran ones. This was attributed to the ability of sulfur atoms in accommodating electrons from nitro group, which facilitate its reduction and therefore the formation of free radicals lethal to parasites.

AROMATIC FLUORINE CHEMISTRY. PART 1. 3,4-DIFLUOROBENZOIC ACID AND DERIVATIVES VIA 3,4-DIFLUOROBENZOTRIFLUORIDE

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