185147-08-4

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluoro-3-methylbenzonitrile is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Chemical Synthesis:
4-Fluoro-3-methylbenzonitrile is employed as a building block in the synthesis of other complex organic molecules. Its presence in the molecular structure can influence the properties and reactivity of the final product, making it a valuable asset in the field of organic chemistry.
Used in Research and Development:
In the context of scientific research, 4-Fluoro-3-methylbenzonitrile is utilized as a model compound to study the effects of fluorination and methylation on the properties of aromatic compounds. This helps researchers understand the underlying chemical principles and develop new strategies for the synthesis of novel compounds.

InChI:InChI=1/C10H5Cl2F3O/c11-7-3-1-6(2-4-7)8(5-16)9(12)10(13,14)15/h1-5H/b9-8-

Upstream product

• 135427-08-6 4-fluoro-3-methylbenzaldehyde 
• 41963-20-6 4-bromo-3-methylbenzonirtile 
• 135205-66-2 N?cyanosuccinimide 
• 139911-27-6 4-fluoro-3-methylphenyl boronic acid 
• 557-21-1 zinc(II) cyanide 
• 95-52-3 2-Fluorotoluene 
• 313546-18-8 (4-cyano-2-methylphenyl)boronic acid 
• 261945-92-0 4-fluoro-3-methylbenzamide 
• 51437-00-4 5-bromo-2-fluorotoluene 

Downstream Products

• 1207543-43-8 C₁₈H₁₆ClNO₃ 
• 856935-35-8 3-(bromomethyl)-4-fluorobenzonitrile 
• 175277-86-8 4-fluoro-N'-hydroxy-3-methylbenzimidamide 
• 1260534-44-8 3-Methyl-4-{4-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzamide 
• 1260539-49-8 3-Methyl-4-{4-oxo-3-(trifluoromethyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile 
• 1260539-50-1 4-{4-Chloro-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-methylbenzonitrile 
• 1260539-51-2 3-methyl-4-{4-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile 
• 1260539-47-6 4-{5-((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methylamino)-3-(trifluoromethyl)-1H-pyrazolo-1-yl}-3-methylbenzonitrile 
• 1260538-70-2 3-methyl-4-{4-(quinolin-3-yl)-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile 
• 1260532-92-0 4-{3-Isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-methylbenzamide 
• 1260538-68-8 4-{3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-methylbenzonitrile 
• 1251116-95-6 4-fluoro-3-methyl-benzimidic acid ethyl ester 
• 1570084-80-8 1-isopropyl-6-methyl-4-oxo-5-(3-(trifluoromethyl)phenyl)-1,4-dihydropyridine-3-carboxylic acid 3-methyl-4-(N-cyano-S-(methyl)sulfinimidoyl)benzylamide 
• 1605324-74-0 C,C-dideutero-C-(4-fluoro-3-methyl-phenyl)-methylamine hydrochloride 

Relevant academic research and scientific papers

Development and Molecular Understanding of a Pd-Catalyzed Cyanation of Aryl Boronic Acids Enabled by High-Throughput Experimentation and Data Analysis

A synthetic method for the palladium-catalyzed cyanation of aryl boronic acids using bench stable and non-toxic N-cyanosuccinimide has been developed. High-throughput experimentation facilitated the screen of 90 different ligands and the resultant statistical data analysis identified that ligand σ-donation, π-acidity and sterics are key drivers that govern yield. Categorization into three ligand groups – monophosphines, bisphosphines and miscellaneous – was performed before the analysis. For the monophosphines, the yield of the reaction increases for strong σ-donating, weak π-accepting ligands, with flexible pendant substituents. For the bisphosphines, the yield predominantly correlates with ligand lability. The applicability of the designed reaction to a wider substrate scope was investigated, showing good functional group tolerance in particular with boronic acids bearing electron-withdrawing substituents. This work outlines the development of a novel reaction, coupled with a fast and efficient workflow to gain understanding of the optimal ligand properties for the design of improved palladium cross-coupling catalysts.

Dual Ligand-Enabled Nondirected C-H Cyanation of Arenes

Aromatic nitriles are key structural units in organic chemistry and, therefore, highly attractive targets for C-H activation. Herein, the development of an arene-limited, nondirected C-H cyanation based on the use of two cooperatively acting commercially available ligands is reported. The reaction enables the cyanation of arenes by C-H activation in the absence of directing groups and is therefore complementary to established approaches.

Fluorination of aryl boronic acids using acetyl hypofluorite made directly from diluted fluorine

Aryl boronic acids or pinacol esters containing EDG were converted in good yields and fast reactions to the corresponding aryl fluorides using the readily obtainable solutions of AcOF. In reactions with aryl boronic acids containing EWG at the para position, there are two competing forces: one directing the fluorination to take place ortho to the boronic acid and the other, toward an ipso substitution. With EWG meta to the boronic acid, substitution ipso to the boron moiety takes place in good yields.

Metal-Catalyzed Carbon-Fluorine Bond Formation

One aspect of the invention relates to a metal-catalyzed conversion of aryl halides and sulfonates to the corresponding aryl fluorides. Another aspect of the invention relates to a metal-catalyzed conversion of heteroaryl halides and sulfonates to the corresponding heteroaryl fluorides. Another aspect of the invention relates to a metal-catalyzed conversion of vinyl halides and sulfonates to the corresponding vinyl fluorides. In certain embodiments, simple fluoride sources, such as AgF and CsF, are used. In certain embodiments, the transformations tolerate a wide range of functional groups, allowing for introduction of fluorine atoms into highly functionalized organic molecules.

Formation of arf from lpdar(f): catalytic conversion of aryl triflates to aryl fluorides

Despite increasing pharmaceutical importance, fluorinated aromatic organic molecules remain difficult to synthesize. Present methods require either harsh reaction conditions or highly specialized reagents, making the preparation of complex fluoroarenes ch

NOVEL CARBOXAMIDES FOR USE AS XA INHIBITORS

The invention relates to the novel substituted carboxamides of general formula (I), wherein A, B and R1 to R5 are defined as in claim 1, the tautomers, enantiomers, diastereomers, mixtures and salts thereof, especially the physiologically salts thereof with inorganic or organic acids or bases, which have valuable properties. The inventive compounds have an antithrombotic effect and are factor Xa inhibitors.

New carboxylic acid amides, the preparation thereof and their use as medicaments

The present invention relates to new substituted carboxylic acid amides of general formula wherein A, B and R1 to R5 are defined as in claim 1, the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable properties.

1,2-Diarylimidazoles as potent, cyclooxygenase-2 selective, and orally active antiinflammatory agents

Series of 1,2-diarylimidazoles has been synthesized and found to contain highly potent and selective inhibitors of the human COX-2 enzyme. The paper describes a short synthesis of the target 1,2-diarylimidazoles starting with aryl nitriles. Different portions of the diarylimidazole (I) were modified to establish SAR. Systematic variations of the substituents in the aryl ring B have yielded very potent (IC50 = 10-100 nm) and selective (1000-12500) inhibitors of the COX-2 enzyme. The study on the influence of substituents in the imidazole ring established that a CF3 group at position 4 gives the optimum oral activity. A number of the diarylimidazoles showed excellent inhibition in the adjuvant induced arthritis model (e.g., ED50 = 0.02 mpk for 22 and 34). The diarylimidazoles are also potent inhibitors of carrageenan-induced edema (ED50 = 9-30 mpk) and hyperalgesia (ED50 = 11- 40 mpk). Several orally active diarylimidazoles show no GI toxicity in the rat and mouse up to 200 mpk.