455-32-3

Basic information

• Product Name: BENZOYL FLUORIDE
• Synonyms: BENZOYL FLUORIDE;Benzoyl fluoride 99%;Benzoylfluoride99%;Benzoic acid fluoride;Benzoyl fluoride,98%
• CAS NO: 455-32-3
• Molecular Formula: C₇H₅FO
• Molecular Weight: 124.11
• EINECS: 207-244-9
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 455-32-3.mol
• Article Data: 123

Chemical Properties

• Melting Point: −28 °C(lit.)
• Boiling Point: 159-161 °C(lit.)
• Flash Point: 120 °F
• Appearance: clear yellow to red-brown liquid
• Density: 1.14 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.17mmHg at 25°C
• Refractive Index: n20/D 1.496(lit.)
• Water Solubility: Hydrolyses in water.
• Sensitive: Lachrymatory
• BRN: 1904977
• CAS DataBase Reference: BENZOYL FLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZOYL FLUORIDE(455-32-3)
• EPA Substance Registry System: BENZOYL FLUORIDE(455-32-3)

Safety Data

• Hazard Codes: C,T,F
• Statements: 10-34
• Safety Statements: 16-26-27-36/37/39-45
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• TSCA: T
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 455-32-3(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow to red-brown liquid

Uses

Different sources of media describe the Uses of 455-32-3 differently. You can refer to the following data:
1. Manufacturing of acyl and other fluorides.
2. Benzoyl fluoride is used as a mild fluorinating agent.

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 
• 98-07-7 Benzotrichlorid 
• 93-97-0 benzoic acid anhydride 
• 618-32-6 Benzoyl bromide 
• 1540-04-1 hexafluoroisopropylidenetriethoxyphosphorane 
• 2078-12-8 trimethylsilyl benzoate 
• 92787-72-9 N-benzhydryl-O-benzoyl-hydroxylamine 
• 67539-05-3 mixed anhydride of α-hydrohexafluoroisobutyric acid and benzoic acid 
• 121-44-8 triethylamine 
• 1584-03-8 perfluoro-2-methylpent-2-ene 
• 65-85-0 benzoic acid 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 373-74-0 methyltrifluorosilane 
• 18220-90-1 4-ethylbenzophenone 
• 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 
• 461-53-0 butanoyl fluoride 
• 57568-25-9 3-Chlor-tetrafluorpropen-2-yl-benzoat 
• 56112-35-7 perfluoroisopropyl phenyl ketone 
• 3389-54-6 n-benzoylpyrrolidine 
• 1484-17-9 S-ethyl thiobenzoate 
• 13163-65-0 6-Methyl-cyclohexen-1-yl-benzoat 

Relevant articles and documents

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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.

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.

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.