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<α-11C>Benzoyl chloride is a key radiochemical intermediate synthesized via palladium-mediated 11C-carbonylation of aryl halides (e.g., iodides or bromides) with [11C]carbon monoxide and a chloride source (e.g., tetrabutylammonium chloride). This intermediate is highly reactive and serves as a versatile precursor for synthesizing diverse 11C-labeled compounds, including aromatic acids, amides, esters, aldehydes, benzyl alcohols, and phenyl ketones, through subsequent reactions with nucleophiles or metalloid reagents. Its utility is demonstrated by high radiochemical yields (up to 95%) in multi-step radiolabeling processes, enabling efficient production of PET tracers for biomedical applications.

128592-81-4

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128592-81-4 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 128592-81-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,8,5,9 and 2 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 128592-81:
(8*1)+(7*2)+(6*8)+(5*5)+(4*9)+(3*2)+(2*8)+(1*1)=154
154 % 10 = 4
So 128592-81-4 is a valid CAS Registry Number.

128592-81-4Relevant academic research and scientific papers

Radiosynthesis of [11C]docetaxel

Van Tilburg,Franssen,Van Der Hoeven,Van Der Meij,Elshove,Lammertsma,Windhorst

, p. 763 - 777 (2004)

Docetaxel (Taxotere) is an accepted chemotherapeutic agent for the treatment of breast cancer and non-small cell lung cancers. A potential means of predicting response is measuring tumor uptake of [11C]docetaxel using Positron Emission Tomograp

11C-Carbonylation through in Situ Generated 11C-Benzoyl Chlorides with Tetrabutylammonium Chloride as Chloride Source

Dahl, Kenneth,Nordeman, Patrik

, p. 2648 - 2651 (2017)

Aromatic 11C-containing acids, amides, esters, and aldehydes were obtained through a novel 11C-carbonylative reaction. In the two-step process, aryl iodides are first reacted with 11CO and tetrabutylammonium chloride in a palladium-mediated reaction to yield 11C-benzoyl chlorides in situ. The crude mixture is then further treated with either a hydroxide, amine, alcohol, or a hydride in a second vial to furnish the final 11C-carbonyl product. The monodentate ligand tri-tert-butylphosphonium tetrafluoroborate was proven to be crucial for obtaining high radiochemical yields (RCY). A wide range of 11C-containing carbonyl compounds were successfully radiolabeled in moderate to excellent RCYs, ranging from 41–93 %. The synthetic retinoic acid tamibarotene was obtained in a RCY of 89 %, whereas the Boc-protected procainamide was labelled in 68 % RCY, which is a significantly increase (2–3 fold) in RCY compared to other published methods.

Carbon-11 labeling of a potent, nonpeptide, AT1-selective angiotensin-II receptor antagonist: MK-996

Mathews,Burns,Dannals,Ravert,Naylor

, p. 729 - 737 (1995)

[α-11C]Benzoyl chloride was synthesized and purified by normal phase HPLC. [11C]MK-996 ([11C]N-[[4'[(2-ethyl-5,7-dimethyl-3H-imidazo [4,5-b]pyridin-3-yl)methyl][1,1'-biphenyl]-2-yl]sulfonyl]- benzamide), a potent and selec

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

Roslin, Sara,Dahl, Kenneth,Nordeman, Patrik

, p. 447 - 454 (2018)

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.

Benzyl [11C]Hippurate as an Agent for Measuring the Activities of Organic Anion Transporter 3 in the Brain and Multidrug Resistance-Associated Protein 4 in the Heart of Mice

Kikuchi, Tatsuya,Okamura, Toshimitsu,Okada, Maki,Ogawa, Masanao,Suzuki, Chie,Wakizaka, Hidekatsu,Yui, Joji,Fukumura, Toshimitsu,Gee, Antony D.,Zhang, Ming-Rong

, p. 5847 - 5856 (2016/07/06)

Multidrug resistance-associated protein 4 (MRP4) and organic anion transporter 3 (OAT3) mediate the efflux of organic anions from the brain and heart. In this study, we have developed a probe for estimating the activity of these transporters in these tiss

CuI-Catalyzed 11C carboxylation of boronic acid esters: A rapid and convenient entry to 11C-labeled carboxylic acids, esters, and amides

Riss, Patrick J.,Lu, Shuiyu,Telu, Sanjay,Aigbirhio, Franklin I.,Pike, Victor W.

supporting information; experimental part, p. 2698 - 2702 (2012/04/17)

Rapid and direct: The carboxylation of boronic acid esters with 11CO2 provides [11C]carboxylic acids as a convenient entry into [11C]esters and [11C]amides (see scheme). This conversion of boronates is tolerant to diverse functional groups (e.g., halo, nitro, or carbonyl). Copyright

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