1,2-Benzene-d4-diamine | CAS 291765-93-0

OVERVIEW
1,2-Benzene-d₄-diamine is a deuterium-labeled analog of o-phenylenediamine (1,2-diaminobenzene), in which four hydrogen atoms on the aromatic ring are substituted with deuterium. This isotopic modification increases the molecular mass by 4 Da while maintaining identical chemical reactivity, making it an excellent tool for isotopic labeling, tracer studies, and advanced spectroscopic analysis.

As a stable isotope-labeled compound, 1,2-benzene-d₄-diamine is highly valuable in analytical chemistry, pharmaceutical synthesis, and materials research. Its isotopic enrichment provides enhanced precision in mass spectrometry (MS), nuclear magnetic resonance (NMR), and kinetic isotope effect (KIE) studies. The compound’s reactive ortho-diamine structure allows it to serve as a precursor for synthesizing deuterated heterocycles, azo dyes, and other aromatic compounds where isotopic substitution aids in mechanistic or degradation pathway elucidation.

CHEMICAL INFORMATION

• Name: 1,2-Benzene-d₄-diamine

• Molecular Formula: C₆D₄(NH₂)₂

• Molecular Weight: 112.17 g/mol

• CAS Number: 291765-93-0

• Isotopic Enrichment: ≥ 98 atom % D

• Chemical Class: Deuterated aromatic diamine; stable isotope-labeled compound

• Stability: Stable under inert and dry conditions; slowly oxidizes on prolonged exposure to air or light, forming colored by-products

APPLICATIONS  of  1,2-Benzene-d4-diamine | CAS 291765-93-0

• Stable Isotope Labeling and Tracer Studies:
  1,2-Benzene-d₄-diamine is widely used as an isotopic tracer in kinetic and mechanistic studies involving aromatic amines and their oxidation products. Its deuterium labeling helps in monitoring reaction progress, identifying intermediates, and understanding substitution mechanisms.

• Analytical Chemistry and Mass Spectrometry (MS):
  Utilized as an internal standard or calibration compound in MS analyses. The +4 Da mass shift enables clear distinction between deuterated and non-deuterated analogs, ensuring precise quantification and isotopic ratio determination.

• NMR Spectroscopy Applications:
  Serves as a valuable reference compound for studying isotope effects on proton relaxation and coupling constants in aromatic systems. Its deuterated structure reduces background hydrogen signals and enhances spectral clarity.

• Precursor for Deuterated Heterocycles:
  Acts as a building block for synthesizing deuterated benzimidazoles, benzotriazoles, and related heterocyclic compounds, which are used in pharmaceuticals, dyes, and catalysis studies.

• Material and Polymer Research:
  Useful as a deuterated monomer in the preparation of labeled poly(o-phenylenediamine) and advanced polymeric materials. Deuteration aids in neutron scattering and spectroscopic investigations of polymer structures and dynamics.

ADVANTAGES  of  1,2-Benzene-d4-diamine | CAS 291765-93-0

• High isotopic enrichment ensures excellent reproducibility and analytical resolution.

• Chemically identical to o-phenylenediamine, enabling straightforward integration into synthetic pathways.

• Non-radioactive, stable isotope for safe handling and long-term storage.

• Provides enhanced signal discrimination in both NMR and MS analyses.

• Ideal for mechanistic, kinetic, and degradation pathway studies of aromatic amines.

HANDLING

• Hazards: Toxic and potentially sensitizing; may cause irritation to skin, eyes, and respiratory tract. Harmful if ingested or absorbed through the skin. May cause discoloration upon oxidation.

• Precautions: Handle with care in a well-ventilated fume hood. Use protective gloves, goggles, and a lab coat. Avoid direct contact and inhalation of dust.

• Storage: Keep container tightly sealed under inert gas. Store in a cool, dry, and light-protected area away from oxidizing agents.

• Disposal: Dispose of according to local environmental and safety regulations. Avoid contamination of water sources or soil.

Safety Note: Due to its reactive amine groups, the compound may slowly polymerize or oxidize; therefore, inert storage and minimal air exposure are recommended for long-term stability.

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 to confirm isotopic and chemical integrity

• Appearance: Off-white crystalline solid

• COA Availability: Supplied with batch-specific Certificate of Analysis confirming isotopic and chemical purity

SUMMARY
1,2-Benzene-d₄-diamine (CAS 291765-93-0) is a high-purity, deuterium-labeled form of o-phenylenediamine used extensively in isotope labeling, analytical research, and organic synthesis. With four deuterium atoms incorporated in the aromatic ring, it provides a reliable and stable isotopic marker for studies in NMR, MS, and reaction kinetics. This compound’s versatility and stability make it indispensable in advanced materials research, pharmaceutical development, and mechanistic organic chemistry.

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