100940-60-1

Basic information

• Product Name: TRIETHYL PHOSPHONOACETATE-13C2
• Synonyms: TRIETHYL PHOSPHONOACETATE-13C2;TRIETHYL PHOSPHONOACETATE-13C2, 99 ATOM % 13C;(Diethoxyphosphinyl)acetic-13C2 acid ethyl ester;13C Labeled triethyl phosphonoacetate
• CAS NO: 100940-60-1
• Molecular Formula: C₈H₁₇O₅P
• Molecular Weight: 226.21
• Product Categories: C-C Bond Formation;Horner-Wadsworth-Emmons Reagents;Olefination
• Mol File: 100940-60-1.mol

Chemical Properties

• Boiling Point: 142-145 °C9 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.13 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.431(lit.)
• CAS DataBase Reference: TRIETHYL PHOSPHONOACETATE-13C2(CAS DataBase Reference)
• NIST Chemistry Reference: TRIETHYL PHOSPHONOACETATE-13C2(100940-60-1)
• EPA Substance Registry System: TRIETHYL PHOSPHONOACETATE-13C2(100940-60-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 100940-60-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
TRIETHYL PHOSPHONOACETATE-13C2 is used as a reagent for the Horner-Emmons modification, a widely employed method in organic chemistry for the synthesis of alkenes. The isotope labeling allows for the tracking and analysis of the compound's behavior during the reaction, providing valuable insights into the reaction mechanism and the role of the reagent in the process.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, TRIETHYL PHOSPHONOACETATE-13C2 can be used as a starting material for the synthesis of isotopically labeled drug candidates. These labeled compounds can then be used in preclinical and clinical studies to investigate the pharmacokinetics, metabolism, and biodistribution of the drug, as well as to study the effects of isotopic substitution on the compound's activity and safety.
Used in Environmental Science:
TRIETHYL PHOSPHONOACETATE-13C2 can also be employed in environmental science for the study of the fate and transport of chemicals in the environment. By using isotopically labeled compounds, researchers can track the behavior of these chemicals in various environmental matrices, such as soil, water, and air, and better understand their degradation pathways and potential impacts on ecosystems.
Used in Analytical Chemistry:
In analytical chemistry, TRIETHYL PHOSPHONOACETATE-13C2 can be used as an internal standard or a reference compound for the quantification and identification of related compounds in complex mixtures. The isotope labeling provides a unique signature that can be easily distinguished from other compounds, allowing for accurate and precise measurements.
Used in Material Science:
TRIETHYL PHOSPHONOACETATE-13C2 can be utilized in the development of new materials, such as polymers and coatings, with specific properties. The isotope labeling can help researchers understand the structure-property relationships in these materials and optimize their synthesis and processing conditions.

Upstream product

• 61898-49-5 ethyl bromoacetate-⁽¹³⁾C₂ 
• 122-52-1 triethyl phosphite 

Downstream Products

• 347384-09-2 14,15-¹³C₂-retinoic acid ethyl ester 
• 172510-17-7 [1,2-13C₂]ethyl (E)-4-benzyloxy-2-butenoate 
• 1026324-81-1 ethyl 7-(4-methoxy-3-nitrophenyl)-(2E,4E,6E)-[1,2-13C₂]hepta-2,4,6-trienoate 
• 347367-53-7 [10,11-13C₂]-(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate 
• 347367-56-0 10,11,14,15-¹³C₄-retinoic acid ethyl ester 
• 237757-03-8 (2E,4R)-<1,2-¹³C>ethyl 4-benzyloxy-2-octadecenoate 
• 141207-97-8 ethyl 5-methyl-7-(2,6,6-trimethyl-1-cyclohexenyl)heptatrienoate 

Relevant articles and documents

The preparation of all-trans uniformly 13C-labeled retinal via a modular total organic synthetic strategy. Emerging central contribution of organic synthesis toward the structure and function study with atomic resolution in protein research

Uniformly [13C20]-labeled all-trans-retinal (1) has been prepared via a convergent modular total organic strategy with high isotope incorporation (>99%) and without isotope dilution starting from commercially available 99% enriched

Preparation of [1,2,3,4,5-13C 5]-5-Amino-4-oxopentanoic Acid (ALA) - Design of a Synthetic Scheme to Prepare Any 13C- and 15N-Isotopomer with High Isotopic Enrichment

5-Amino-4-oxopentanoic acid (5-aminolevulinic acid) is a precursor in the biosynthesis of the biologically active porphyrins such as chlorophyll, bacteriochlorophyll, heme, etc. These systems are central in photosynthesis, oxygen transport, electron transport, etc. In this paper we describe a simple scheme to prepare any isotopomer of 5-aminolevulinic acid in a few steps in high yield. Using a similar scheme, levulinic acid can now also be prepared in any isotopomeric form. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

A simple efficient synthesis of [23,24]-13C2-labeled bile salts as NMR probes of protein-ligand interactions

The synthesis of [23,24]-13C2-labeled bile salts is achieved through a steroidal side chain degradation and isotopic regeneration strategy. Three common bile acids were degraded to the corresponding C22 aldehyde by an oxidative decarboxylation followed by ozonolysis. The side chain was subsequently regenerated via a Horner-Emmons reaction using an ylide generated from 13C2-labeled bromoacetic acid. These compounds were used as probes of protein-bile salt interactions using two- and three-dimensional NMR techniques.

Synthesis of isotopically labeled all-trans retinals for DNP-enhanced solid-state NMR studies of retinylidene proteins

Three all-trans retinals containing multiple 13C labels have been synthesized to enable dynamic nuclear polarization enhanced solid-state magic angle spinning NMR studies of novel microbial retinylidene membrane proteins including proteorhodpsi

Syntheses of 13C2-labelled 11Z-retinals

To enable solid-state NMR investigations of the rhodopsin chromophore and its photointermediates, a series of 11Z-retinal isotopomers have been synthesised containing pairs of adjacent 13C labels at C9/C10, C10/C11 or C11/C12, respectively. The C9 labelled carbon atom was introduced through the Heck reaction of a 13C-labelled Weinreb acrylamide derivative, and the label at the C12 position derived from a 13C-containing ethoxy Bestmann-Ohira reagent. The 13C labels at C10 and C11 were introduced through the reaction of β-ionone with labelled triethyl phosphonoacetate.

Synthesis of (12,13-(13)C2)retinal and (13,14-(13)C2)retinal: a strategy to prepare multiple-(13)C-labeled conjugated systems

(12,13-(13)C2)Retinal, (13,14-(13)C2)retinal, (19-(13)C)retinal and (20-(13)C)retinal (1) were prepared in a simple fashion in high yield via a consecutive strategy.The key step is the reaction of a N-methoxy-N-methylamide with an alkyllithium or a Grignard reagent.The preparation of the required N-methoxy-N-methylamide is discussed.In this scheme, only three commercially available (13)C-labeled starting materials (ethyl bromoacetate, acetonitrile and methyl iodide) are sufficient to construct retinals with any possible combination of (13)C labeling in the conjugated tail end.This strategy is applicable to the preparation of many other conjugated systems, such as retinoids, carotenoids and polyenes.