• 1. An approach to biodegradable star polymeric architectures using disulfide coupling?
  Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. Davis Chem. Commun., 2008, 6582-6584
• 2. An approach for correlating the structural and electrical properties of Zr4+-modified SrBi4Ti4O15/SBT ceramic
  Priyambada Nayak,Tanmaya Badapanda,Anil Kumar Singh,Simanchalo Panigrahi RSC Adv., 2017,7, 16319-16331
• 3. Acetylcholinesterase amperometric detection system based on a cobalt(II) tetraphenylporphyrin-modified electrode
  Analyst, 1996,121, 1123-1126
• 4. An aptasensor for the detection of ampicillin in milk using a personal glucose meter
  Xixi Li,Nanwei Zhu,Ruohan Li,Qinpu Zhang Anal. Methods, 2020,12, 3376-3381
• 5. An apparatus for testing water by measurement of its electrical conductivity
  Analyst, 1912,37, 538-543

• Solvents and Organic Chemicals Organic Compounds Organohalogen compounds Acyl halides Acyl chlorides

Chloroacetyl-d2 Chloride (CAS No. 159301-43-6): An Overview of Its Properties, Applications, and Recent Research

Chloroacetyl-d2 Chloride (CAS No. 159301-43-6) is a deuterated derivative of chloroacetyl chloride, a versatile reagent in organic synthesis and chemical biology. This compound is characterized by the substitution of two hydrogen atoms with deuterium, which imparts unique properties that make it valuable in various scientific applications. In this comprehensive overview, we will explore the chemical properties, synthesis methods, and recent research advancements involving Chloroacetyl-d2 Chloride.

Chemical Properties and Structure

Chloroacetyl-d2 Chloride (CAS No. 159301-43-6) has the molecular formula C2HClD2O and a molecular weight of approximately 98.97 g/mol. The presence of deuterium atoms (D) in place of hydrogen atoms (H) significantly affects the physical and chemical properties of the molecule. Deuterium, being twice as heavy as hydrogen, results in a higher boiling point and reduced reactivity compared to its non-deuterated counterpart, chloroacetyl chloride.

The structure of Chloroacetyl-d2 Chloride consists of a chloroacetyl group (-ClCHD2CO-) with a chlorine atom and two deuterium atoms attached to the carbon atom. This unique structure makes it an excellent reagent for isotopic labeling and kinetic studies in organic chemistry and biochemistry.

Synthesis Methods

The synthesis of Chloroacetyl-d2 Chloride typically involves the reaction of deuterated acetic acid (CH3COOD) with thionyl chloride (SOCl2). The reaction proceeds via the following steps:

• Deuteration of acetic acid to form deuterated acetic acid (CH3COOD).
• Reaction of deuterated acetic acid with thionyl chloride to form the corresponding acyl chloride.
• Purification and isolation of the final product, Chloroacetyl-d2 Chloride.

This synthetic route ensures high yields and purity, making it suitable for various applications in research and industry.

Applications in Organic Synthesis

Chloroacetyl-d2 Chloride is widely used in organic synthesis as an acylating agent. Its reactivity is similar to that of chloroacetyl chloride, but the presence of deuterium atoms provides additional advantages. For instance, it can be used to introduce deuterium labels into organic molecules, which is crucial for studying reaction mechanisms and kinetic isotope effects.

In recent studies, researchers have utilized Chloroacetyl-d2 Chloride to synthesize deuterated derivatives of biologically active compounds. These labeled compounds are valuable for pharmacokinetic studies and metabolic profiling, providing insights into drug metabolism and distribution in biological systems.

Applications in Chemical Biology

In chemical biology, Chloroacetyl-d2 Chloride has found applications in the development of isotopically labeled probes for studying protein-protein interactions and enzyme kinetics. The deuterium-labeled reagent can be incorporated into peptides or small molecules to create probes that are more stable and less prone to degradation compared to their non-deuterated counterparts.

A recent study published in the Journal of Medicinal Chemistry demonstrated the use of Chloroacetyl-d2 Chloride-labeled peptides to investigate the binding kinetics of a novel protein inhibitor. The results showed that the deuterium-labeled probe provided enhanced stability and improved detection sensitivity, leading to more accurate kinetic measurements.

Recent Research Advancements

The field of isotopic labeling has seen significant advancements in recent years, driven by the increasing demand for precise analytical tools in drug discovery and development. Researchers have explored various applications of deuterated reagents like Chloroacetyl-d2 Chloride, including:

• Mechanism Elucidation: Deuteration can help elucidate reaction mechanisms by providing insights into transition states and intermediates.
• Kinetic Isotope Effects: The study of kinetic isotope effects using deuterated reagents can provide valuable information about reaction rates and pathways.
• Bioanalytical Applications: Deuteration enhances the stability and detectability of labeled compounds in bioanalytical assays, improving the accuracy and reliability of results.
• Metabolic Studies: Deuteration can be used to track the metabolism of drugs and other bioactive compounds, providing insights into their pharmacokinetics.

A notable example is a study published in Nature Communications that utilized deuterated reagents like Chloroacetyl-d2 Chloride

Safety Considerations

Safety is a critical consideration when handling any chemical reagent. While Chloroacetyl-d2 Chloride

In conclusion, Chloroacetyl-d2 Chloride

• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
• 2034271-14-0(2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide)