66134-67-6

Basic information

• Product Name: Succinimido p-fluorobenzoate
• Synonyms: 2,5-Pyrrolidinedione, 1-[(4-fluorobenzoyl)oxy]-;Succinimido p-fluorobenzoate;2,5-Dioxopyrrolidin-1-yl 4-fluorobenzoate
• CAS NO: 66134-67-6
• Molecular Formula: C₁₁H₈FNO₄
• Molecular Weight: 237.18
• Mol File: 66134-67-6.mol
• Article Data: 23

Chemical Properties

• Melting Point: 113-114 °C
• Boiling Point: 354.873°C at 760 mmHg
• Flash Point: 168.422°C
• Appearance: /
• Density: 1.462g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Succinimido p-fluorobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Succinimido p-fluorobenzoate(66134-67-6)
• EPA Substance Registry System: Succinimido p-fluorobenzoate(66134-67-6)

Safety Data

• Hazardous Substances Data: 66134-67-6(Hazardous Substances Data)

Usage

Chemical Properties

Colourless solid

InChI:InChI=1/C11H8FNO4/c12-8-3-1-7(2-4-8)11(16)17-13-9(14)5-6-10(13)15/h1-4H,5-6H2

Upstream product

• 17592-54-0 2,5-dioxopyrrolidin-1-yl formate 
• 352-34-1 4-fluoro-1-iodobenzene 
• 619-66-9 4-Carboxybenzaldehyde 
• 60444-78-2 succinimidyl 4-formylbenzoate 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 459-57-4 4-fluorobenzaldehyde 
• 201230-82-2 carbon monoxide 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 403-43-0 4-fluorobenzoyl chloride 
• 1196658-43-1 (4-((2,5-Dioxopyrrolidin-1-yloxy)carbonyl)phenyl)(thiophen-2-yl)iodonium trifluoroacetate 
• 456-22-4 4-Fluorobenzoic acid 
• 459-56-3 4-fluorobenzylic alcohol 
• 74124-79-1 di(succinimido) carbonate 
• 105832-38-0 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 

Downstream Products

• 1233519-63-5 FB-[(N-Me)G₂₄, (N-Me)I₂₆]hIAPP(22-27) 
• 366-79-0 p-fluorohippuric Acid 
• 1440324-25-3 2-[(1S,2S,4S)-(bicyclo[2.2.1]hept-5-en-2-yl)ethyl]-4-fluorobenzamide 
• 738587-13-8 C₂₀H₂₀F₂N₄O₄S₂ 

Relevant articles and documents

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Abundant aromatic carboxylic acids exist in great structural diversity from nature and synthesis. To date, the synthetically valuable decarboxylative functionalization of benzoic acids is realized mainly by transition-metal-catalyzed decarboxylative cross couplings. However, the high activation barrier for thermal decarboxylative carbometalation that often requires 140 °C reaction temperature limits both the substrate scope as well as the scope of suitable reactions that can sustain such conditions. Numerous reactions, for example, decarboxylative fluorination that is well developed for aliphatic carboxylic acids, are out of reach for the aromatic counterparts with current reaction chemistry. Here, we report a conceptually different approach through a low-barrier photoinduced ligand to metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation strategy, which generates a putative high-valent arylcopper(III) complex, from which versatile facile reductive eliminations can occur. We demonstrate the suitability of our new approach to address previously unrealized general decarboxylative fluorination of benzoic acids.

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