1285695-14-8

Basic information

• Product Name: [13C]-9-Methylfluorene-9-carboxylic acid
• Synonyms: [13C]-9-Methylfluorene-9-carboxylic acid;PUPWRKQSVGUBQS-UJKGMGNHSA-N
• CAS NO: 1285695-14-8
• Molecular Formula: C15H12O2
• Molecular Weight: 225.26358
• Mol File: 1285695-14-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [13C]-9-Methylfluorene-9-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [13C]-9-Methylfluorene-9-carboxylic acid(1285695-14-8)
• EPA Substance Registry System: [13C]-9-Methylfluorene-9-carboxylic acid(1285695-14-8)

Safety Data

• Hazardous Substances Data: 1285695-14-8(Hazardous Substances Data)

Usage

General Description

[13C]-9-Methylfluorene-9-carboxylic acid is a chemical compound containing a carbon-13 isotope, which is commonly used in research and industrial applications. It is a derivative of the aromatic hydrocarbon 9-methylfluorene, with a carboxylic acid group attached to the ninth carbon atom. [13C]-9-Methylfluorene-9-carboxylic acid has properties that make it useful for various purposes, including as a labeling reagent for tracking metabolic pathways, as a precursor for the synthesis of other organic compounds, and as a starting material for the production of pharmaceuticals and agrochemicals. Its unique structure and isotopic composition make it a valuable tool in chemical and biological research, as well as in the development of new materials and products.

Upstream product

• 2523-37-7 9-methylfluorene 
• 1111-72-4 carbon dioxide 
• 486-25-9 9-fluorenone 
• 4425-82-5 9-methylene-fluorene 
• 6311-22-4 9-methyl-9H-fluoren-9-ol 

Relevant articles and documents

SYSTEM PROVIDING CONTROLLED DELIVERY OF GASEOUS CO FOR CARBONYLATION REACTIONS

A carbonylation system comprising at least one carbon monoxide producing chamber and at least one carbon monoxide consuming chamber forming an interconnected multi-chamber system, said interconnection allowing carbon monoxide to pass from the at least one carbon monoxide producing chamber to the at least one carbon monoxide consuming chamber, said at least one carbon monoxide producing chamber containing a reaction mixture comprising a carbon monoxide precursor and a catalyst, said at least one carbon monoxide consuming chamber being suitable for carbonylation reactions, said interconnected multi- chamber system being sealable from the surrounding atmosphere during carbonylation.

Ex situ generation of stoichiometric and substoichiometric 12CO and 13CO and its efficient incorporation in palladium catalyzed aminocarbonylations

A new technique for the ex situ generation of carbon monoxide (CO) and its efficient incorporation in palladium catalyzed carbonylation reactions was achieved using a simple sealed two-chamber system. The ex situ generation of CO was derived by a palladium catalyzed decarbonylation of tertiary acid chlorides using a catalyst originating from Pd(dba)2 and P(tBu)3. Preliminary studies using pivaloyl chloride as the CO-precursor provided an alternative approach for the aminocarbonylation of 2-pyridyl tosylate derivatives using only 1.5 equiv of CO. Further design of the acid chloride CO-precursor led to the development of a new solid, stable, and easy to handle source of CO for chemical transformations. The synthesis of this CO-precursor also provided an entry point for the late installment of an isotopically carbon-labeled acid chloride for the subsequent release of gaseous [ 13C]CO. In combination with studies aimed toward application of CO as the limiting reagent, this method provided highly efficient palladium catalyzed aminocarbonylations with CO-incorporations up to 96%. The ex situ generated CO and the two-chamber system were tested in the synthesis of several compounds of pharmaceutical interest and all of them were labeled as their [ 13C]carbonyl counterparts in good to excellent yields based on limiting CO. Finally, palladium catalyzed decarbonylation at room temperature also allowed for a successful double carbonylation. This new protocol provides a facile and clean source of gaseous CO, which is safely handled and stored. Furthermore, since the CO is generated ex situ, excellent functional group tolerance is secured in the carbonylation chamber. Finally, CO is only generated and released in minute amounts, hence, eliminating the need for specialized equipment such as CO-detectors and equipment for running high pressure reactions.