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

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

• 74124-79-1 di(succinimido) carbonate 
• 456-22-4 4-Fluorobenzoic acid 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 459-56-3 4-fluorobenzylic alcohol 
• 619-66-9 4-Carboxybenzaldehyde 
• 60444-78-2 succinimidyl 4-formylbenzoate 
• 17592-54-0 2,5-dioxopyrrolidin-1-yl formate 
• 352-34-1 4-fluoro-1-iodobenzene 
• 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 
• 105832-38-0 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 

Downstream Products

• 148671-42-5 3-(4-fluorophenyl)-3-oxo-2-(pyridin-4-yl)propanenitrile 
• 1093733-09-5 2-[3-[5-(4-fluoro-benzoylamino)-1-(4-methoxy-benzyloxycarbonyl)-pentyl]-ureido]-pentanedioic acid bis-(4-methoxy-benzyl)ester 
• 141762-27-8 N-succinimidyl 4-[18F]fluorobenzoate 
• 1011623-88-3 N-(3-hydroxypropyl)-4-fluorobenzamide 
• 953747-69-8 6-(4-fluorobenzamido)hexanoic acid 

Relevant articles and documents

Radical Decarboxylative Carbometalation of Benzoic Acids: A Solution to Aromatic Decarboxylative Fluorination

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.

Formation of 1-hydroxymethylene-1,1-bisphosphinates through the addition of a silylated phosphonite on various trivalent derivatives

An easily handled one-pot synthetic procedure was previously developed for the synthesis of bisphosphinates starting from acyl chlorides. Herein, other trivalent derivatives as acid anhydrides and activated esters were tested to form various bisphosphinates. This modulation of the reactivity can be controlled according to the nature of the acid derivative for the use of sensitive and functionalized substrates.

Small molecular PET photographic developer of target chemokine receptor CXCR4

The invention relates to a small molecular PET photographic developer of a target chemokine receptor CXCR4 and a preparation method of the small molecular PET photographic developer. According to thesmall molecular PET photographic developer of the target

N-Doped Yellow TiO2 Hollow Sphere-Mediated Visible-Light-Driven Efficient Esterification of Alcohol and N-Hydroxyimides to Active Esters

Herein we report a simple synthetic protocol for N-doped yellow TiO2 (N-TiO2) hollow spheres as an efficient visible-light-active photocatalyst using aqueous titanium peroxocarbonate complex (TPCC) solution as precursor and NH4OH. In the developed strategy, the ammonium ion of TPCC and NH4OH acts as nitrogen source and structure-directing agent. The synthesized N-TiO2 hollow spheres are capable of promoting the synthesis of active esters of N-hydroxyimide and alcohol through simultaneous selective oxidation of alcohol to aldehyde followed by cross-dehydrogenative coupling (CDC) under ambient conditions upon irradiation of visible light. It is possible to develop a novel and cost-effective one-pot strategy for the synthesis of important esters and amides on gram scale using the developed strategy. The catalytic activity of N-TiO2 hollow spheres is much superior to that of other reported N-TiO2 samples as well as TiO2 with varying morphology.

RADIOACTIVE COMPOUND FOR DIAGNOSIS OF MALIGNANT MELANOMA AND USE THEREOF

The present invention provides a novel radioactive compound for imaging malignant melanoma and a use thereof as a contrast agent for PET imaging.

MYELOPEROXIDASE IMAGING AGENTS

Provided herein are compounds useful as imaging agents. Exemplary compounds provided herein are useful as myeloperoxidase imaging agents using positron emission tomography or fluorescence imaging techniques. Methods for preparing the compounds provided herein and diagnostic methods using radiolabeled and unlabeled compounds are also provided.

Atmospheric oxidative catalyst-free cross-dehydrogenative coupling of aldehydes with N-hydroxyimides

Cross-dehydrogenative coupling (CDC) reactions of aldehydes with N-hydroxyimidates such as N-hydroxysuccinimide (NHSI), N-hydroxyphthalimide (NHPI) under catalyst-free conditions is described. Moreover, the desired products can be obtained simply by recrystallization from ethanol. This method is also applicable to the synthesis of amides in excellent yields. A radical mechanism of the type shown in Scheme 4 is proposed based upon the inhibition of the reaction in the presence of TEMPO.

Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands

Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.

Iron-Nitrate-Catalyzed Oxidative Esterification of Aldehydes and Alcohols with N-Hydroxyphthalimide: Efficient Synthesis of N-Hydroxyimide Esters

An Fe(NO3)3·9H2O-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide (NHPI) or N-hydroxysuccinimide (NHSI) and aldehydes or alcohols in air is described. This transformation represents an efficient approach to the preparation of N-hydroxyimide ester derivatives in moderate to excellent yields, and has a wide substrate scope.

Prototypic 18F-Labeled Argininamide-Type Neuropeptide Y Y1R Antagonists as Tracers for PET Imaging of Mammary Carcinoma

The neuropeptide Y (NPY) Y1 receptor (Y1R) selective radioligand (R)-Nα-(2,2-diphenylacetyl)-Nω-[4-(2-[18F]fluoropropanoylamino)butyl]aminocarbonyl-N-(4-hydroxybenzyl)argininamide ([18F]23), derived from the high-affinity Y1R antagonist BIBP3226, was developed for imaging studies of Y1R-positive tumors. Starting from the argininamide core bearing amine-functionalized spacer moieties, a series of fluoropropanoylated and fluorobenzoylated derivatives was synthesized and studied for Y1R affinity. The fluoropropanoylated derivative 23 displayed high affinity (Ki = 1.3 nM) and selectivity toward Y1R. Radiosynthesis was accomplished via 18F-fluoropropanoylation, yielding [18F]23 with excellent stability in mice; however, the biodistribution study revealed pronounced hepatobiliary clearance with high accumulation in the gall bladder (>100 %ID/g). Despite the unfavorable biodistribution, [18F]23 was successfully used for imaging of Y1R positive MCF-7 tumors in nude mice. Therefore, we suggest [18F]23 as a lead for the design of PET ligands with optimized physicochemical properties resulting in more favorable biodistribution and higher Y1R-dependent enrichment in mammary carcinoma.