5122-16-7

Basic information

• Product Name: PENTAFLUOROPHENACYL BROMIDE
• Synonyms: (BROMOACETYL)PENTAFLUOROBENZENE;2,3,4,5,6-PENTAFLUOROPHENACYL BROMIDE;PENTAFLUOROPHENACYL BROMIDE;2-BROMO-2',3',4',5',6'-PENTAFLUOROACETOPHENONE;(bromoacetyl) pentafluorbenzene;2-Bromo-2',3',4',5',6'-pentafluoroacetophenone, 2-Bromo-1-(perfluorophenyl)ethan-1-one
• CAS NO: 5122-16-7
• Molecular Formula: C₈H₂BrF₅O
• Molecular Weight: 289
• Mol File: 5122-16-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 30-32°C
• Boiling Point: 247 °C at 760 mmHg
• Flash Point: 103.2 °C
• Appearance: low melting point solid
• Density: 1.862 g/cm³
• Vapor Pressure: 0.0263mmHg at 25°C
• Refractive Index: 1.478
• CAS DataBase Reference: PENTAFLUOROPHENACYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PENTAFLUOROPHENACYL BROMIDE(5122-16-7)
• EPA Substance Registry System: PENTAFLUOROPHENACYL BROMIDE(5122-16-7)

Safety Data

• Hazard Codes: T
• Statements: 34-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 1759
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 5122-16-7(Hazardous Substances Data)

Usage

General Description

Pentafluorophenacyl bromide is a chemical compound with the formula C8H3BrF5O. It is a clear, colorless liquid that is primarily used as a reagent in organic synthesis. Pentafluorophenacyl bromide is a versatile compound that is often used to introduce the pentafluorophenacyl group into organic molecules through nucleophilic substitution reactions. PENTAFLUOROPHENACYL BROMIDE is highly reactive and can easily react with nucleophiles, such as alcohols, amines, and thiols, to form the corresponding esters, amides, and thioesters. Additionally, pentafluorophenacyl bromide has also been used as a precursor for the synthesis of various pharmaceutical and agrochemical products. However, it is important to handle this compound with caution, as it can be corrosive and toxic if not properly handled.

InChI:InChI=1/C8H2BrF5O/c9-1-2(15)3-4(10)6(12)8(14)7(13)5(3)11/h1H2

Upstream product

• 879-05-0 2,3,4,5,6-pentafluorophenylmagnesium bromide 
• 652-29-9 2',3',4',5',6'-pentafluoroacetophenone 
• 5121-99-3 --methanol 
• 652-31-3 2,3,4,5,6-pentafluorobenzamide 
• 773-82-0 Pentafluorobenzonitrile 

Downstream Products

• 1422972-57-3 4,4'-bis(perfluorophenyl)-2,2'-bithiazole 
• 1235031-48-7 C₂₂H₁₁F₅N₂O₂ 
• 1059608-77-3 diphenyl pentafluorophenacylphosphonate 
• 70656-66-5 (C₂H₅)3GeOC(C₆F₅)CH₂ 
• 25959-55-1 C₁₄HBrF₁₀ 
• 25798-78-1 2-Bromo-1,1-bis-pentafluorophenyl-ethanol 
• 74-96-4 ethyl bromide 
• 652-29-9 2',3',4',5',6'-pentafluoroacetophenone 
• 70656-65-4 Triethyl-(1-pentafluorophenyl-vinyloxy)-silane 
• 939428-45-2 2-(pentafluorophenyl)imidazo[1,2-a]pyridine 

Relevant articles and documents

Usnic Acid Enaminone-Coupled 1,2,3-Triazoles as Antibacterial and Antitubercular Agents

(+)-Usnic acid, a product of secondary metabolism in lichens, has displayed a broad range of biological properties such as antitumor, antimicrobial, antiviral, anti-inflammatory, and insecticidal activities. Interested by these pharmacological activities and to tap into its potential, we herein present the synthesis and biological evaluation of new usnic acid enaminone-conjugated 1,2,3-triazoles 10-44 as antimycobacterial agents. (+)-Usnic acid was condensed with propargyl amine to give usnic acid enaminone 8 with a terminal ethynyl moiety. It was further reacted with various azides A1-A35 under copper catalysis to give triazoles 10-44 in good yields. Among the synthesized compounds, saccharin derivative 36 proved to be the most active analogue, inhibiting Mycobacterium tuberculosis (Mtb) at an MIC value of 2.5 μM. Analogues 16 and 27, with 3,4-difluorophenacyl and 2-acylnaphthalene units, respectively, inhibited Mtb at MIC values of 5.4 and 5.3 μM, respectively. Among the tested Gram-positive and Gram-negative bacteria, the new derivatives were active on Bacillus subtilis, with compounds 18 [3-(trifluoromethyl)phenacyl] and 29 (N-acylmorpholinyl) showing inhibitory concentrations of 41 and 90.7 μM, respectively, while they were inactive on the other tested bacterial strains. Overall, the study presented here is useful for converting natural (+)-usnic acid into antitubercular and antibacterial agents via incorporation of enaminone and 1,2,3-triazole functionalities.

Anomalous Reaction of Pentafluorophenacyl Bromide with Hexamethylenetetramine. Structure of the Product

The title compounds condense in chloroform to yield tetrafluorobenzo-1,3,5,7-tetraazatetracyclo3,7.15,9.01,9>tetradecan-10-one (1), a reaction proposed to involve both an ortho fluorine elimination and two Stevens