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

• 98-07-7 Benzotrichlorid 
• 93-97-0 benzoic acid anhydride 
• 108-86-1 bromobenzene 
• 201230-82-2 carbon monoxide 
• 1733-63-7 1,2,2-triphenylethan-1-one 
• 100-52-7 benzaldehyde 
• 98-88-4 benzoyl chloride 
• 96887-05-7 C₃CsF₇O₂S 
• 100-51-6 benzyl alcohol 
• 3872-23-9 Copper(I) trifluoromethanethiolate 
• 98-86-2 acetophenone 
• 7783-56-4 antimony(III) fluoride 
• 75-73-0 carbon tetrafluoride 
• 71-43-2 benzene 

Downstream Products

• 1493-02-3 formyl fluoride 
• 65-85-0 benzoic acid 
• 557-99-3 acetyl fluoride 
• 430-71-7 propionyl fluoride 
• 63053-84-9 1-O-benzoyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose 
• 63028-91-1 1-O-benzoyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose 
• 56112-35-7 perfluoroisopropyl phenyl ketone 
• 1484-17-9 S-ethyl thiobenzoate 
• 13163-65-0 6-Methyl-cyclohexen-1-yl-benzoat 
• 93-99-2 benzoic acid phenyl ester 
• 371-22-2 fluorophosphoric acid diethyl ester 
• 1759-68-8 N-benzoylcyclohexylamine 
• 33925-53-0 2-Benzoyl-2,2-diphenylacetonitrile 
• 353-36-6 1-fluoroethane 

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.

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.