3880-99-7

Usage

Uses

Used in Pharmaceutical Industry:
BENZOIC ACID-ALPHA-13C is used as a research compound for the development and analysis of pharmaceutical products. Its carbon-13 labeling allows for precise tracking and identification of the molecule in various chemical reactions and metabolic pathways, aiding in the optimization of drug synthesis and efficacy.
Used in Food Preservation:
BENZOIC ACID-ALPHA-13C is used as a food preservative to extend the shelf life of various products. Its ability to inhibit the growth of bacteria, molds, and yeasts contributes to maintaining the quality and safety of food items.
Used in Chemical Production:
BENZOIC ACID-ALPHA-13C is used as a key component in the synthesis of various chemicals. Its unique properties and carbon-13 labeling make it an ideal candidate for the development of new chemical compounds and materials.
Used in Research and Analytical Applications:
BENZOIC ACID-ALPHA-13C is used as a tracer molecule in research and analytical work. The presence of carbon-13 enables researchers to monitor the molecule's behavior and interactions within complex systems, providing valuable insights into chemical processes and mechanisms.

InChI:InChI=1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)/i7+1

Upstream product

• 108-86-1 bromobenzene 
• 1111-72-4 carbon dioxide 
• 51956-33-3 [13C]barium carbonate 
• 591-51-5 phenyllithium 
• 1641-69-6 [13C]Carbon monoxide 
• 71-43-2 benzene 
• 42181-97-5 benzyl <(18)O> alcohol 
• 52947-05-4 [α-13C]benzoyl chloride 
• 54522-91-7 [α-13C]-benzyl alcohol 
• 1278530-64-5 C₇⁽¹³⁾CH₆O₃ 
• 515-42-4 sodium phenylsulfonate 
• 110-89-4 piperidine 
• 155638-70-3 13C,²H>benzaldehyde 
• 98-88-4 benzoyl chloride 

Downstream Products

• 36712-21-7 methyl [carboxyl-¹³C]benzoate 
• 10383-88-7 acetophenone-13C=O 
• 852244-84-9 [carbonyl-13C]-S-2-pyridyl benzothioate 
• 69838-86-4 [α-13C]benzyl bromide 
• 219793-23-4 [1-13C]benzyl-1H-1,2,3-benzotriazole 
• 219793-24-5 [[1-13C]-1-phenyl-2-(1,1,1-trimethylsilyl)ethyl]-1H-1,2,3-benzotriazole 
• 220077-31-6 (3R,5S)-2,3,5,6-tetrahydro-5-phenyl-3-phenyl[13C]methyl-N-(tert-butyloxycarbonyl)-4H-1,4-oxazin-2-one 
• 219793-25-6 [2-13C]-(1H-1,2,3-benzotriazol-1-yl)-1,2-diphenyl-3-(1,1,1-trimethylsilyl)propan-1-one 
• 143215-26-3 C₁₉⁽¹³⁾CH₁₆O 
• 143215-27-4 C₁₉⁽¹³⁾CH₁₄O₂ 
• 122189-10-0 1,3-Diphenyl-1-<1-(13)C>propanone 
• 122189-11-1 1,3-Diphenyl-1-<1-(13)C>propanone azine 
• 122189-13-3 1,1'-Azobis(1,3-<1-(13)C>-diphenylpropane) 

Relevant academic research and scientific papers

Bimodal Fluorescence/Magnetic Resonance Molecular Probes with Extended Spin Lifetimes

Bimodal molecular probes combining nuclear magnetic resonance (NMR) and fluorescence have been widely studied in basic science, as well as clinical research. The investigation of spin phenomena holds promise to broaden the scope of available probes allowi

Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative

We report an effective, operationally simple, and environmentally friendly system for the synthesis of tertiary amides by the oxidative coupling of aromatic or aliphatic aldehydes with amines mediated by riboflavin tetraacetate (RFTA), an inexpensive organic photocatalyst, and visible light using oxygen as the sole oxidant. The method is based on the oxidative power of an excited flavin catalyst and the relatively low oxidation potential of the hemiaminal formed by amine to aldehyde addition.

Coordination behaviors of diphenylketene adsorbed in the nanocages of zeolite NaY and AgY

We investigated in detail how polar cumulene molecules like diphenylketene were accommodated in faujasite zeolite pores based on 13C CP/MAS and DD/MAS NMR analyses as well as quantum chemical calculations after adsorbing the molecule into the zeolite NaY or AgY having “hard” sodium ions or “soft” silver ions. Since the diphenylketene has such a specific structure that a carbonyl group (a hard base) is accumulated by a carbon-carbon double bond (a soft π base), which is conjugated with two benzene rings (soft π bases), it is possible for the diphenylketene to adopt multicoordination modes to different metal ions in the zeolite. Compared with the coordination modes of benzophenone and 1,1-diphenylethene adsorbed in the NaY and AgY, those of diphenylketene were identified, and specific coordination behaviors in the zeolite’s supercages were classified depending on the hard or soft metal characters: The C=O and phenyl coordination modes to Na+ in NaY prevail, while the C=C and phenyl coordination to Ag+ in AgY is favored. We also unveiled the difference in the molecular mobility depending on the types of cations in the zeolite by comparing the 13C CP/MAS and DD/MAS NMR spectra.

Palladium-Catalyzed Carbon Isotope Exchange on Aliphatic and Benzoic Acid Chlorides

An operationally simple protocol for a palladium-catalyzed 13CO and 14CO exchange with activated aliphatic and benzoic carbonyls is presented. Several 13C and 14C building blocks, natural product derivatives, an

Copper(I)-Catalyzed Desulfinative Carboxylation of Sodium Sulfinates using Carbon Dioxide

A copper(I)-catalyzed desulfinative carboxylation of sodium sulfinates using carbon dioxide has been developed. This reaction showed wide functional group tolerance. A series of sodium aryl- and alkenylsulfinates could be converted into the corresponding carboxylic acids in good to excellent yields. Additionally, the reaction mechanism was studied by in situ NMR analysis and isotopic labeling experiments.

Insights into the asymmetric heterogeneous catalysis in porous organic polymers: Constructing A TADDOL-Embedded chiral catalyst for studying the structure-activity relationship[ ]

Construction of porous organic polymers (POPs) as asymmetric catalysts remains as an important but challenging task. Herein, we exploit the "bottom-up" strategy to facilely synthesize an α,α, α,α-tetraaryl-1,3-dioxolane-4,5-dimethanol (TADDOL)-based chiral porous polymer (TADDOL-CPP) for highly efficient asymmetric catalysis. Constructed through the covalent linkages among the three-dimensional rigid monomers, TADDOL-CPP possesses hierarchical porous structure, high Brunauer-Emmett-Teller (BET) surface area, together with abundant and uniformly-distributed chiral sites. In the presence of [Ti(OiPr)4], TADDOL-CPP acts as a highly efficient and recyclable catalyst in the asymmetric addition of diethylzinc (Et2Zn) to aromatic aldehydes. Based on the direct observation of the key intermediates, the reaction mechanism has been revealed by solid-state 13C magic-angle spinning (MAS) NMR spectroscopy. In combination with the catalytic testing results, characterization on the working catalyst provides further information for understanding the structure-activity relationship. We suggest that the catalytic activity of TADDOL-CPP is largely affected by the structural rigidity, cooperative catalysis, local chiral environment, and hierarchical porous framework. We expect that the information obtained herein will benefit to the designed synthesis of robust POP catalysts toward practical applications.

A hydrogen peroxide-responsive hyperpolarized 13C MRI contrast agent

We report a new reaction-based approach for the detection of hydrogen peroxide (H2O2) using hyperpolarized 13C magnetic resonance imaging (13C MRI) and the H2O 2-mediated oxidation of α-ketoacids to carboxylic acids. 13C-Benzoylformic acid reacts selectively with H2O 2 over other reactive oxygen species to generate 13C- benzoic acid and can be hyperpolarized using dynamic nuclear polarization, providing a method for dual-frequency detection of H2O2. Phantom images collected using frequency-specific imaging sequences demonstrate the efficacy of this responsive contrast agent to monitor H2O 2 at pre-clinical field strengths. The combination of reaction-based detection chemistry and hyperpolarized 13C MRI provides a potentially powerful new methodology for non-invasive multi-analyte imaging in living systems.

Imidazolium ionic liquids as solvents for cerium(IV)-mediated oxidation reactions

Use of imidazolium ionic liquids as solvents for organic transformations with tetravalent cerium salts as oxidizing agents was evaluated. Good solubility was found for ammonium hexanitratocerate(IV) (ceric ammonium nitrate, CAN) and cerium(IV) triflate in 1-alkyl-3-methylimidazolium triflate ionic liquids. Oxidation of benzyl alcohol to benzaldehyde in 1-ethyl-3-methylimidazolium triflate was studied by in-situ FTIR spectroscopy and 13C NMR spectroscopy on carbon-13-labeled benzyl alcohol. Careful control of the reaction conditions is necessary because ammonium hexanitratocerate(IV) dissolved in an ionic liquid can transform benzyl alcohol not only into benzaldehyde but also into benzyl nitrate or benzoic acid. The selectivity of the reaction of cerium(IV) triflate with benzyl alcohol in dry ionic liquids depends on the degree of hydration of cerium(IV) triflate: anhydrous cerium(IV) triflate transforms benzyl alcohol into dibenzyl ether, whereas hydrated cerium(IV) triflate affords benzaldehyde as the main reaction product. Reactions of ammonium hexanitratocerate(IV) with organic substrates other than benzyl alcohol have been explored. 1,4-Hydroquinone is quantitatively transformed into 1,4-quinone. Anisole and naphthalene are nitrated. For the cerium-mediated oxidation reactions in ionic liquids, high reaction temperatures are an advantage because under these conditions smaller amounts of byproducts are formed.

Partial oxygen migration in the photochemical wolff rearrangement - α-Oxocarben-Oxiren-isomerization or intermolecular mechanism?

Crossover experiments between isotopomeric species of 2-diazo-1-oxo-1-phenylethane (18O, 13C, D) establish beyond doubt that the oxygen migration accompanying the photochemical Wolff rearrangement is not the result of intermolecular

Reaction of magnesium pinacolone enolate with benzaldehyde: Polar or ET mechanism?

The carbonyl-carbon kinetic isotope effect (KIE) and the substituent effect were measured for the reaction of magnesium pinacolone enolate (CH2=C(OMgBr)C(CH3)3, 1) with benzaldehyde. The results were compared with those for lithium enolate (CH2=C(OLi)C(CH3)3, 2). A normal carbonyl-carbon KIE, a medium-sized Hammett ρ value and the results of chemical probe experiments indicated that the reaction of 1 proceeds via the polar mechanism as in the reaction of 2.