455-32-3

Usage

Uses

1. Chemical Industry:
Benzoyl fluoride is used as a mild fluorinating agent for the synthesis of various organic compounds, particularly in the production of acyl and other fluorides. Its mild fluorinating properties make it a preferred choice in chemical reactions where harsher fluorinating agents may cause unwanted side reactions or degradation of the desired product.
2. Pharmaceutical Industry:
In the pharmaceutical industry, benzoyl fluoride is utilized as a reagent in the synthesis of various drugs and drug intermediates. Its ability to selectively introduce fluorine atoms into organic molecules without causing significant side reactions makes it a valuable tool in the development of new pharmaceutical compounds.
3. Material Science:
Benzoyl fluoride can also be used in the field of material science for the development of novel materials with specific properties. Its mild fluorinating ability allows for the controlled introduction of fluorine atoms into polymers and other materials, potentially enhancing their performance characteristics such as chemical stability, thermal resistance, and mechanical strength.

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 925, 1974 DOI: 10.1021/ja00810a052The Journal of Organic Chemistry, 49, p. 3216, 1984 DOI: 10.1021/jo00191a035

Hazard

High toxicity.

InChI:InChI=1/C7H5FO/c8-7(9)6-4-2-1-3-5-6/h1-5H

Upstream product

• 532-32-1 sodium benzoate 
• 368-43-4 phenylsulfonyl fluoride 
• 98-88-4 benzoyl chloride 
• 98-07-7 Benzotrichlorid 
• 93-97-0 benzoic acid anhydride 
• 108-86-1 bromobenzene 
• 201230-82-2 carbon monoxide 
• 618-32-6 Benzoyl bromide 
• 1540-04-1 hexafluoroisopropylidenetriethoxyphosphorane 
• 2078-12-8 trimethylsilyl benzoate 
• 98-08-8 α,α,α-trifluorotoluene 
• 1733-63-7 1,2,2-triphenylethan-1-one 
• 92787-72-9 N-benzhydryl-O-benzoyl-hydroxylamine 
• 100-52-7 benzaldehyde 

Downstream Products

• 2689-59-0 (furan-2-yl)(phenyl)methanone 
• 1493-02-3 formyl fluoride 
• 65-85-0 benzoic acid 
• 373-74-0 methyltrifluorosilane 
• 93-89-0 benzoic acid ethyl ester 
• 592-94-9 octanoic acid fluoride 
• 448-61-3 2,4,6-triphenylpyrylium tetrafluoroborate 
• 30057-74-0 N-(1-oxo-1,3-diphenylpropan-2-yl)benzamide 
• 557-99-3 acetyl fluoride 
• 430-71-7 propionyl fluoride 
• 611-94-9 4-Methoxybenzophenone 
• 134-84-9 4-Methylbenzophenone 
• 354-34-7 trifluoroacetyl fluoride 
• 461-53-0 butanoyl fluoride 

Relevant academic research and scientific papers

FAR INFRARED SPECTRA AND BARRIERS TO INTERNAL ROTATION OF BENZALDEHYDE, BENZOYL FLUORIDE, BENZOYL CHLORIDE AND ACETOPHENONE

The far infrared (250-40 cm-1) spectra of gaseous benzaldehyde, benzoyl fluoride, benzoyl chloride and acetophenone have been recorded.The fundamental CHO torsion for benzaldehyde has been observed at 110.85 cm-1 with three excited states at 109.51, 106.52 and 104.17 cm-1 along with several "hot bands" arising from the frequency bending modes.The corresponding fundamental for benzoyl fluoride has been observed at 63.36 cm-1 with one well defined excited state at 61.91 cm-1.Similarly, bands observed at 44.6 and 49.5 cm-1 in the spectra of benzoyl chloride and acetophenone, respectively, have been assigned to the fundamental CXO torsions of these molecules.These data have allowed for the determination of the twofold barrier which governs the internal rotation of the CXO moiety and have been found to be 1611 cm-1 (4.61 kcal mol-1), 1739 cm-1 (4.97 kcal mol-1), 1162 cm-1 (3.32 kcal mol-1) and 1103 cm-1 (3.15 kcal mol-1) for the aldehyde, fluoride, chloride and ketone, respectively.These results are compared to previously obtained values for two of the molecules and to some corresponding barriers for several related molecules.

Proton Sponge Hydrofluoride as a Soluble Fluoride Ion Source

Proton Sponge (PS) hydrofluoride has been prepared and is totally soluble in acetonitrile; this system was used to generate carbanions from hexafluoropropene and to form carbon-fluorine bonds by reaction with 2,4,6-trichloropyrimidine and by reaction with benzoyl chloride (Proton Sponge hydrochloride is insoluble in acetonitrile).

Acyl fluorides from carboxylic acids, aldehydes, or alcohols under oxidative fluorination

We describe a novel reagent system to obtain acyl fluorides directly from three different functional group precursors: carboxylic acids, aldehydes, or alcohols. The transformation is achieved via a combination of trichloroisocyanuric acid and cesium fluoride, which facilitates the synthesis of various acyl fluorides in high yield (up to 99%). It can be applied to the late-stage functionalization of natural products and drug molecules that contain a carboxylic acid, an aldehyde, or an alcohol group.

Gram-Scale Preparation of Acyl Fluorides and Their Reactions with Hindered Nucleophiles

A series of acyl fluorides was synthesized at 100 mmol scale using phase-transfer-catalyzed halogen exchange between acyl chlorides and aqueous bifluoride solution. The convenient procedure consists of vigorous stirring of the biphasic mixture at room temperature, followed by extraction and distillation. Isolated acyl fluorides (usually 7-20 g) display excellent purity and can be transformed into sterically hindered amides and esters when treated with lithium amide bases and alkoxides under mild conditions.

Metal-free approach for hindered amide-bond formation with hypervalent iodine(iii) reagents: application to hindered peptide synthesis

A new bio-inspired approach is reported for amide and peptide synthesis using α-amino esters that possess a potential activating group (PAG) at the ester residue. To activate the ester functionality under mild metal-free conditions, we exploited the facile dearomatization of phenols with hypervalent iodine(iii) reagents. Using a pyridine-hydrogen fluoride complex, highly reactive acyl fluoride intermediates can be successfully generated, thereby allowing for the smooth formation of sterically hindered amides and peptides from bulky amines and α-amino esters, respectively.

Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes

Cyclopropanes are an important class of building blocks in organic synthesis. Herein, a ring-opening/arylcarboxylation/acylation cascade reaction for the 1,3-difunctionalization of aryl cyclopropanes enabled by cooperative NHC and organophotoredox catalysis is reported. The cascade works on monosubstituted cyclopropanes that are in contrast to the heavily investigated donor–acceptor cyclopropanes more challenging to be difunctionalized. The key step is a radical/radical cross coupling of a benzylic radical generated in the photoredox catalysis cycle with a ketyl radical from the NHC catalysis cycle. The transformation features metal-free reaction conditions and tolerates a diverse range of functionalities.

Fluorination method

In order to overcome the problems of high cost and low stability of the existing fluorination reagents for preparing acyl fluoride, sulfonyl fluoride and phosphoryl fluoride compounds, the invention provides a fluorination method, which comprises the following operation steps of: adding a fluorination reagent into a substrate, wherein the fluorination reagent comprises cations M and anions, the anions are selected from one or more of perfluoropolyether chain carboxylic acid anions as shown in the specification: CF3(OCF2)nCO2, wherein n is selected from 1-10; the substrate comprises a carboxylic acid compound, a sulfonic acid compound, a phosphoric acid compound and a phosphine oxide compound; and carrying out fluorination reaction to obtain acyl fluoride, sulfonyl fluoride and phosphoryl fluoride products. According to the fluorination method provided by the invention, the perfluoropolyether chain carboxylate is used as a fluorination reagent, so that the dehydroxylation fluorination reaction of the carboxylic acid compound, the sulfonic acid compound and the phosphoric acid compound and the fluorination reaction of the phosphine oxide compound are realized, the product yield isrelatively high, and the fluorination method has relatively good universality for different substrates.

Deoxyfluorination of Carboxylic, Sulfonic, Phosphinic Acids and Phosphine Oxides by Perfluoroalkyl Ether Carboxylic Acids Featuring CF2O Units

The deoxyfluorination of carboxylic, sulfonic, phosphinic acids and phosphine oxides is a fundamentally important approach to access acyl fluorides, sulfonyl fluorides and phosphoric fluorides, thus the development of inexpensive, stable, easy-to-handle, versatile, and efficient deoxyfluorination reagents is highly desired. Herein, we report the use of potassium salts of perfluoroalkyl ether carboxylic acids (PFECA) featuring CF2O units as deoxyfluorination reagents, which are generated mainly as by-products in the manufacture of hexafluoropropene oxide (HFPO). The synthesis of acyl fluorides, sulfonyl fluorides and phosphoric fluorides can be realized via carbonic difluoride (COF2) generated in situ from thermal degradation of the PFECA salt.

Deoxyfluorination of Carboxylic Acids with CpFluor: Access to Acyl Fluorides and Amides

3,3-Difluoro-1,2-diphenylcyclopropene (CpFluor), a bench-stable fluorination reagent, has been developed in the deoxyfluorination of carboxylic acids to afford various acyl fluorides. This all-carbon-based fluorination reagent enabled the efficient transformation of (hetero)aryl, alkyl, alkenyl, and alkynyl carboxylic acids to the corresponding acyl fluorides under the neutral conditions. This deoxyfluorination method was featured by the synthesis of acyl fluorides with in-situ formed CpFluor, as well as the one-pot amidation reaction of carboxylic acids via in-situ formed acyl fluorides.

Direct amidation of acid fluorides using germanium amides

Amide functional groups are an essential linkage that are found in peptides, proteins, and pharmaceuticals and new methods are constantly being sought for their formation. Here, a new method for their preparation is presented where germanium amides Ph3GeNR2convert acid fluorides directly to amides. These germanium amides serve to abstract the fluorine atom of the acid fluoride and transfer their amide group -NR2to the carbonyl carbon, and so function as amidation reagents.