25569-77-1

Usage

Uses

Used in Pharmaceutical Industry:
4-FLUOROBENZOIC ANHYDRIDE is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its unique structure allows it to be a key component in the development of new therapeutic agents.
Used in Organic Synthesis:
4-FLUOROBENZOIC ANHYDRIDE is used as a reagent in organic synthesis, particularly for the production of benzoylthiophenes. These compounds are known to be allosteric enhancers (AE) of agonist activity at the A1 adenosine receptor, which has potential applications in the treatment of various diseases and conditions.

InChI:InChI=1/C14H8F2O3/c15-11-5-1-9(2-6-11)13(17)19-14(18)10-3-7-12(16)8-4-10/h1-8H

Upstream product

• 456-22-4 4-Fluorobenzoic acid 
• 459-57-4 4-fluorobenzaldehyde 
• 459-56-3 4-fluorobenzylic alcohol 
• 403-43-0 4-fluorobenzoyl chloride 
• 352-34-1 4-fluoro-1-iodobenzene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 1178005-93-0 C₁₆H₉FO₄ 
• 345-83-5 4-fluorobenzophenone 
• 1474012-51-5 C₁₅H₁₀FNO₂ 
• 1228801-86-2 rac-2-(4-fluorophenyl)-4-methyloxazol-5(4H)-one 
• 704-84-7 ethenyl 4-fluorobenzoate 
• 2795-53-1 2,6-Difluor-fluorenon 
• 60045-27-4 3-phenylpropionic acid 3-phenylpropyl ester 
• 90172-20-6 3-phenyl-1-propyl p-fluorobenzoate 
• 347-84-2 1-(4-fluorophenyl)-2-phenylethanone 
• 1583-56-8 4-fluorobenzoyl fluoride 

Relevant academic research and scientific papers

Preparation method of symmetric aromatic anhydride compound

The invention discloses a preparation method of a symmetric aromatic anhydride compound, the preparation method comprises the following steps: dissolving alpha-terpilenol and pyridine in a solvent, adding an aroyl chloride solution, and reacting for 8-16 hours to obtain the symmetric aromatic anhydride compound. The alpha-terpilenol and the aroyl chloride are used as raw materials, and the method has the advantages of being easy to operate, mild in reaction condition, high in safety, simple in technological process and post-treatment, low in cost, high in yield of part of products and the like, and is very beneficial to industrialization.

Visible light-induced transformation of aldehydes to esters, carboxylic anhydrides and amides

A transition metal- and organophotocatalyst free synthesis of esters, carboxylic anhydrides and amides from aldehydes induced by visible-light has been reported. The proposed methodology can be carried out by the use of sunlight or artificial visible light as a blue LED source. The methodology has a very broad applicability and the desired products are obtained in very satisfactory yields.

Cu-MOF: An efficient heterogeneous catalyst for the synthesis of symmetric anhydrides: Via the C-H bond activation of aldehydes

In this paper, an efficient and straightforward synthetic approach for the preparation of a number of symmetric carboxylic anhydrides was reported using Cu2(BDC)2(DABCO) as an efficient heterogeneous catalyst via the C-H bond activation of aldehydes with excellent yields and simple work up. This C-H bond activation reaction appears simple and convenient, has a wide substrate scope and makes use of cheap, abundant, and easily available reagents. The Cu-MOF catalyst was recycled and reused four times without any loss of catalytic activity.

An investigation on practical synthesis of carboxylic acid derivatives using p-toluenesulfonyl chloride

Carboxylic acid derivatives are well recognized as important class of reagents frequently used in the preparation of a variety of fine or special chemicals such as amides, esters, peptides, drugs, and dyes. Although several methods were developed for the preparation of these compounds, many of them present difficulties, including low yield, high reaction temperature, harsh reaction conditions, tedious work-up, and incompatibility with scale-up. Methods: The synthesis of carboxylic anhydrides is developed through the reaction of carboxylic acids with TsCl in the presence of K2CO3 and acetonitrile as a solvent under ultrasound irradiation and conventional conditions. In addition, one-pot synthesis of acyl azides was carried out in the presence of produced carboxylic anhydrides and the addition of sodium azide under identical condition. Results: A series of carboxylic anhydrides and acyl azides were synthesized using TsCl under ultrasound irradiation and conventional stirring with simple procedure, mild reaction conditions, high yields, and scale-up ability without any restriction. In most cases, the reaction under ultrasound irradiation was better in both yields and the reaction times compared to the conventional method. Conclusion: A convenient method has been developed for the preparation of carboxylic anhydrides and acyl azides under ultrasound irradiation and conventional stirring. The present method is practical and a highly effective alternative for previous reports. The major advantages of this method are: (i) simplicity of the procedure (ii) high yields and high purity of product (iii) scale-up capacity without considerable limitation in conventional system. Under ultrasound irradiation short reaction times as compared to conventional method are observed; yields are comparable to or better than conventional method.

Metal-free oxidative self-coupling of aldehydes or alcohols to symmetric carboxylic anhydrides

A metal-free synthesis of symmetrical anhydrides has been developed starting from aldehydes, both aliphatic and aromatic or primary benzylic alcohols. The reaction occurs at room temperature and makes use of trichloroisocyanuric acid (TCCA) as an oxidant providing the desired carboxylic anhydrides in satisfactory yields.

Sc(OTf)3-catalyzed synthesis of anhydrides from twisted amides

A novel synthesis of anhydrides from twisted amides is reported. Sc(OTf)3 catalysis in the presence of water is used to synthesize anhydrides in one step from amides without external nucleophiles. Mechanistic studies indicate that the coordination of the catalyst is critical to induce the challenging N-C activation step. This process further highlights the utility of twisted amides in organic synthesis. Notably, the reaction indicates that twisted amides based on the glutarimide scaffold are more reactive than carboxylic acid anhydrides under the developed conditions, which opens the door to controlled sequential catalysis through amide N-C bond cleavage.

Anhydrides from aldehydes or alcohols via oxidative cross-coupling

A novel type of metal-free oxidative cross-coupling for the synthesis of symmetrical and mixed anhydrides from aldehydes or benzylic alcohols has been developed. The aldehydes or alcohols were converted in situ into their corresponding acyl chlorides, which were then reacted with an array of carboxylic acids. The methodology has a general applicability, and was successfully employed to prepare either aromatic or aliphatic symmetrical anhydrides and mixed anhydrides, which are very unstable compounds.

Light-enabled synthesis of anhydrides and amides

Recently, we have demonstrated that the photogeneration of Vilsmeier-Haack reagents is possible using only dimethylformamide (DMF) and tetrabromomethane (CBr4) in the bromination of alcohols. Extending these findings to carboxylic acid substrates has produced a mild and facile approach to the in situ formation of symmetric anhydrides, which were conveniently converted to amide derivatives in a one-pot process. The efficient protocols discussed herein are marked by use of UVA LEDs (365 nm), which have reduced the reaction times and come with a low setup cost.

Synthesis of acylsilanes by copper(I)-catalyzed addition of silicon nucleophiles onto acid derivatives

The transition metal-catalyzed transfer of silicon nucleophiles onto various electrophiles has recently gained considerable attention, due to the now readily available silicon pro-nucleophiles such as silylboronates. Our interest lies in the addition of such species to acid derivatives for the generation of acylsilanes. We report herein an efficient method to synthesize these compounds, starting from easy-to-form anhydrides, with very good yields. Copyright

Carboxylic acid anhydrides via Pd-catalyzed carbonylation of aryl halides at atmospheric CO pressure

A convenient method has been developed, which allows for the direct transformation of aryl iodides into the corresponding carboxylic acid anhydrides via Pd-catalyzed carbonylation under atmospheric CO pressure. The Royal Society of Chemistry 2012.