162611-87-2

Basic information

• Product Name: [carbonyl-11C]benzophenone
• Synonyms: [carbonyl-11C]benzophenone
• CAS NO: 162611-87-2
• Molecular Weight: 181.211
• Mol File: 162611-87-2.mol

Chemical Properties

• CAS DataBase Reference: [carbonyl-11C]benzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: [carbonyl-11C]benzophenone(162611-87-2)
• EPA Substance Registry System: [carbonyl-11C]benzophenone(162611-87-2)

Safety Data

• Hazardous Substances Data: 162611-87-2(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 934-56-5 trimethyl(phenyl)stannane 
• 10456-04-9 11C-carbon monooxide 
• 98-80-6 phenylboronic acid 
• 1483-72-3 diphenyliodonium chloride 
• 960-16-7 tributylphenylstannane 
• 143-66-8 sodium tetraphenyl borate 
• 128592-81-4 <α-11C>benzoyl chloride 
• 175354-30-0 tris(1H,1H,2H,2H-perfluorooctyl)phenyltin 
• 17763-67-6 Phenyl triflate 
• 73177-92-1 (2-methylphenyl)(phenyl)iodonium tosylate 
• 722-56-5 diphenyliodonium nitrate 
• 1483-73-4 diphenyliodonium bromide 
• 2217-79-0 diphenyliodonium iodide 

Relevant articles and documents

Rapid mild syntheses of [11C]benzophenones by Pd(0)-catalysed11C-carbonylative coupling of iodoarenes with phenyltributylstannane in DME-water

Palladium(0)-catalysed 11C-carbonylative coupling of iodoarenes (RC6H4I; R = H, 2-Me, 3-Me, 4-F, and 4-CF3) with phenyltributylstannane for 1 min in 1,2-dimethoxyethane-water (4: 1 v/v) at room temperature gave [11C]benzophenones (RC6H411COPh) in high radiochemical yields (58-82%. decay-corrected from trapped [11C]carbon monoxide). The efficiency of [11C]carbon monoxide trapping from a single pass into the reaction medium was 4.5-6.2%. The reaction conditions are suitable for the rapid, efficient introduction of cyclotron-produced carbon-11 (t1/2 = 20.3 min) into substituted benzophenones as prospective labelling agents and radiopharmaceuticals for application in medical imaging with positron emission tomography. Copyright

An evaluation of a high-pressure 11CO carbonylation apparatus

[11C]Carbon monoxide (11CO) is a versatile building block for the synthesis of Positron Emission Tomography (PET) radioligands. However, the difficulty of trapping 11CO in a small solvent volume has limited its utility. We

Palladium(II)-mediated 11C-carbonylative coupling of diaryliodonium salts with organostannanes-a new, mild and rapid synthesis of aryl [11C]ketones

Palladium(II)-mediated [11C]carbonylative coupling of diaryliodonium salts with aryltributylstannanes for 1 min in DME-water (4:1 v/v) at RT gives a new mild and rapid route to aryl [11C]ketones. Substituted aryltributylstannanes cou

Reaction of 11C-benzoyl chlorides with metalloid reagents: 11C-labeling of benzyl alcohols, benzaldehydes, and phenyl ketones from [11C]CO

In this article, we describe the carbon-11 (11C, t1/2?=?20.4?minutes) labeling of benzyl alcohols, benzaldehydes, and ketones using an efficient 2-step synthesis in which 11C-carbon monoxide is used in an initial palladium-mediated reaction to produce 11C-benzoyl chloride as a key intermediate. In the second step, the obtained 11C-benzoyl chloride is further treated with a metalloid reagent to furnish the final 11C-labeled product. Benzyl alcohols were obtained in moderated to high non-isolated radiochemical yields (RCY, 35%–90%) with lithium aluminum hydride or lithium aluminum deuteride as metalloid reagent. Changing the metalloid reagent to either tributyltin hydride or sodium borohydride, allowed for the reliable syntheses of 11C-benzaldehydes in RCYs ranging from 58% to 95%. Finally, sodium tetraphenylborate were utilized to obtain 11C-phenyl ketones in high RCYs (77%–95%). The developed method provides a new and efficient route to 3 different classes of compounds starting from aryl iodides or aryl bromides.

Palladium-mediated [11C]carbonylation at atmospheric pressure: A general method using xantphos as supporting ligand

The palladium-catalyzed [11C]carbonylation of aryl halides and triflates was achieved at atmospheric pressure by employing xantphos as the supporting ligand. Aryl halides were converted into their corresponding [ 11C]amides in good t

Methods for purifying radiolabelled compounds

One aspect of the present invention relates to a method of purifying radiolabelled compounds comprising a) loading onto a fluorous polymer a radiolabelled compound precursor comprising a fluoroalkyl tin moiety; b) reacting the radiolabelled compound precursor with a radiolabel delivering compound to give a radiolabelled compound, wherein the fluoroalkyl tin moiety is replaced by a radiolabel; and c) eluting the radiolabelled compound from the fluorous polymer.

Synthesis of 11C-/13C-Ketones by Suzuki Coupling

Aryl triflates, methyl- or arylboronic acids, and a low concentration of [11C]carbon monoxide were employed on small scale in the syntheses of fifteen 11C-labelled ketones using palladium-mediated Suzuki coupling reactions. The reagents were confined in a micro-autoclave and heated at 150 °C for 5 min. The reaction required the presence of LiBr, but no additional base. The 11C-labelled products were obtained with decay-corrected radiochemical yields in the range 10-70% and with high specific radioactivity (150-640 GBq/μmol). The radiochemical purity of the final products exceeded 98%. One 13C-substituted ketone ([ 13C]-2′-benzonaphthone) was prepared and analysed by NMR spectroscopy for confirmation of the labelling position. The reference compound 2′-benzonaphthone was prepared by a palladium-catalysed reaction between sodium tetraphenylborate and 2-naphthoyl chloride. 2-Thienyl p-tolyl ketone, 4-nitrophenyl 2-thienyl ketone and 2-naphthyl 2-thienyl ketone were prepared by reactions between thiophene-2-boronic acid and the corresponding acid chlorides. The presented approach is novel and seems to be an efficient method for the synthesis of a wide range of 11C- as well as 13C-labelled ketones. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Synthesis of [11C]/(13C)amines via carbonylation followed by reductive animation

Twelve 11C-labelled amines were prepared via 11C-carbonylation followed by reductive amination. The 11C-carbonylation was performed in the presence of tetrakis(triphenylphosphine)palladium using aryl iodides or aryl trifla