Diethyl malonate-d2 | CAS 4303-49-5

OVERVIEW
Diethyl malonate-d₂ is a selectively deuterated isotopologue of diethyl malonate, an important intermediate and reagent in organic synthesis. In this compound, two hydrogen atoms on the methylene carbon (–CH₂–) group of diethyl malonate are replaced by deuterium, producing a +2 Da increase in molecular weight while retaining the same structural and reactive characteristics as the non-deuterated analog.

Due to its isotopic labeling, diethyl malonate-d₂ is extensively used as a stable isotope tracer and internal standard in mass spectrometric and NMR studies. It is particularly valuable in mechanistic organic chemistry, isotope effect studies, and kinetic investigations involving malonate derivatives. The compound’s high isotopic purity and chemical stability make it an indispensable reagent in both research and industrial applications.

CHEMICAL INFORMATION

• Name: Diethyl malonate-d₂

• Molecular Formula: C₇H₁₀D₂O₄

• Molecular Weight: 162.18 g/mol

• CAS Number: 4303-49-5

• Isotopic Enrichment: ≥ 98 atom % D

• Chemical Class: Deuterated carboxylic acid ester; stable isotope-labeled compound

• Stability: Chemically stable under ambient conditions; hydrolyzes in strong acids or bases

APPLICATIONS  of  Diethyl malonate-d2 | CAS 4303-49-5

• Stable Isotope Labeling in Mechanistic Studies:
  Diethyl malonate-d₂ is widely used to investigate reaction pathways in organic chemistry, especially in condensation and alkylation reactions. The deuterium label helps monitor isotope effects and mechanistic steps through NMR and MS techniques.

• Analytical Standard for GC-MS and LC-MS:
  Employed as an internal standard for quantifying diethyl malonate and related esters in analytical and environmental samples. The +2 Da isotopic shift enables precise mass spectral discrimination and correction for instrumental variability.

• Organic Synthesis Intermediate:
  Serves as a labeled precursor for the synthesis of deuterated compounds such as amino acids, barbiturates, and substituted acetic acids. Its active methylene group allows for a wide variety of chemical transformations including alkylation, acylation, and condensation reactions.

• NMR Spectroscopy Studies:
  Used in ¹H and ²H NMR spectroscopy for chemical shift calibration and for studying exchange processes, proton transfer mechanisms, and isotopic substitution effects.

• Kinetic Isotope Effect (KIE) Research:
  Ideal for measuring kinetic isotope effects in proton-transfer reactions, providing insights into reaction dynamics, transition states, and energy barriers in organic and enzymatic systems.

ADVANTAGES  of  Diethyl malonate-d2 | CAS 4303-49-5

• Precisely labeled at the methylene position, providing defined isotopic incorporation

• High isotopic enrichment (≥98 atom % D) ensures reliable and reproducible data

• Chemically identical reactivity to native diethyl malonate for accurate mechanistic comparisons

• Compatible with a wide range of analytical and synthetic techniques

• Non-radioactive and safe to handle under standard laboratory conditions

HANDLING

• Hazards: May cause irritation to eyes, skin, and respiratory tract. Avoid inhalation and prolonged contact.

• Precautions: Handle in well-ventilated areas while wearing gloves, goggles, and protective clothing.

• Storage: Keep tightly closed in inert containers at room temperature. Avoid exposure to heat, flame, and moisture.

• Spill and Disposal: In case of spills, absorb with inert materials (e.g., vermiculite). Dispose of waste according to local chemical safety and environmental regulations.

Safety Note: Although not acutely toxic, diethyl malonate-d₂ should be handled using standard chemical hygiene practices.

QUALITY & SPECIFICATION

• Chemical Purity: ≥ 98 %

• Isotopic Enrichment: ≥ 98 atom % D

• Water Content: ≤ 0.05 %

• Analytical Verification: Characterized by ¹H NMR, ²H NMR, IR spectroscopy, and GC-MS

• Appearance: Clear to faint yellow liquid

• COA Provided: Each batch is accompanied by a Certificate of Analysis verifying isotopic enrichment and chemical identity

SUMMARY
Diethyl malonate-d₂ (CAS 4303-49-5) is a high-purity, stable isotope-labeled analog of diethyl malonate widely used in synthetic chemistry, analytical method development, and mechanistic studies. Its deuterium substitution provides a valuable tool for kinetic isotope effect measurements, NMR analyses, and mass spectrometric quantification. Chemically stable, safe, and versatile, diethyl malonate-d₂ continues to serve as a fundamental reagent for researchers exploring isotopic effects and molecular reaction dynamics.