1,2-Diformylhydrazine: Properties, Uses & FAQs

1,2-Diformylhydrazine is a bifunctional hydrazine derivative bearing two formyl groups that serves as a versatile building block in organic synthesis and coordination chemistry research.

Chemical Name

1,2-Diformylhydrazine

Synonyms

N,N'-Diformylhydrazine; Hydrazine-1,2-dicarbaldehyde

Molecular Formula

C₂H₄N₂O₂

Molecular Weight

88.06 g/mol

Functional Groups

Two formyl (–CHO) groups flanking a hydrazine (–NH–NH–) core

Primary Application

Organic synthesis building block; ligand precursor in coordination chemistry

SKU

W135234

What Is 1,2-Diformylhydrazine?

1,2-Diformylhydrazine (molecular formula C₂H₄N₂O₂, MW 88.06 g/mol) is the simplest N,N'-diacylhydrazine in which both nitrogen atoms of the hydrazine core each carry a formyl (–CHO) substituent. The compound belongs to the class of hydrazine derivatives and is closely related to formohydrazide chemistry. Its symmetric, bifunctional structure makes it particularly attractive as a molecular building block: the two carbonyl groups can participate in condensation reactions with amines or other nucleophiles, while the hydrazine nitrogen atoms can coordinate to metal centres or engage in hydrogen-bonding networks.

Because of its small size and high nitrogen-oxygen content, 1,2-diformylhydrazine is also of interest in energetic-material and heterocyclic-synthesis research, where it serves as a precursor to triazole, oxadiazole, and related ring systems.

Physical and Chemical Properties

1,2-Diformylhydrazine is typically described as a crystalline solid at room temperature. Key physicochemical characteristics include:

• Molecular formula: C₂H₄N₂O₂
• Molecular weight: 88.06 g/mol
• Functional groups: Two aldehyde/formyl carbonyl groups and a central hydrazine (N–N) bond
• Solubility: Expected to be soluble in polar solvents such as water, methanol, and DMSO due to the hydrophilic nature of both the formyl and hydrazine moieties; solubility in non-polar solvents is anticipated to be low
• Reactivity: The formyl groups are electrophilic and can condense with primary amines, hydrazines, and hydroxylamines; the N–N bond and lone pairs on nitrogen can coordinate to transition metals

Specific melting point, boiling point, and density values should be confirmed from the certificate of analysis supplied with each lot of Aladdin SKU W135234.

Synthesis and Research Applications

1,2-Diformylhydrazine finds utility in several areas of synthetic and materials chemistry:

1. Heterocyclic synthesis: The compound can serve as a 1,2-dinucleophilic or 1,2-dielectrophilic component in multicomponent reactions aimed at constructing five- and six-membered nitrogen-containing heterocycles, including triazines, oxadiazoles, and diazines.
2. Schiff base and imine formation: Each formyl group can condense with a primary amine to form an imine (Schiff base) linkage, enabling the construction of bis-imine chelate ligands widely used in coordination chemistry and catalysis.
3. Metal complex preparation: The hydrazine N–N unit combined with pendant carbonyl or imine groups creates a polydentate coordination environment suitable for binding first-row transition metals (Fe, Co, Ni, Cu, Zn) and others, with relevance to catalytic and magnetic-property studies.
4. Polymer and material science: Bifunctional acylhydrazine units are explored as dynamic-covalent crosslinkers in hydrazone-based dynamic covalent chemistry, self-healing materials, and stimuli-responsive networks.

Researchers should optimise reaction conditions (solvent, temperature, pH) for each specific transformation, as the compound's dual functionality can lead to oligomerisation or undesired side reactions if conditions are not carefully controlled.

Handling, Storage, and Safety Considerations

As with all hydrazine-derived compounds, 1,2-diformylhydrazine should be treated with appropriate caution in the laboratory:

• Personal protective equipment: Use nitrile gloves, safety glasses, and a laboratory coat when handling. Work in a well-ventilated fume hood to avoid inhalation of dust or vapours.
• Storage: Store in a cool, dry, well-ventilated area away from heat sources, oxidising agents, and strong acids or bases. Keep the container tightly sealed to prevent moisture uptake and maintain product integrity.
• Stability: The compound may be sensitive to moisture and prolonged exposure to light; storage under inert atmosphere (nitrogen or argon) is recommended for long-term stability.
• Waste disposal: Dispose of waste in accordance with local, national, and institutional regulations governing hydrazine-containing materials.

Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for SKU W135234 before use. Specific hazard classifications, first-aid measures, and regulatory information are detailed therein.

Ordering and Specifications for Aladdin SKU W135234

Aladdin Scientific offers 1,2-Diformylhydrazine under SKU W135234. When ordering or evaluating this reagent, researchers and procurement teams should verify:

• Purity: Check the certificate of analysis (CoA) for lot-specific purity data (typically reported by HPLC or elemental analysis).
• Available pack sizes: Contact Aladdin Scientific or visit the product page for current pack-size options and pricing.
• Lead time: Delivery timelines may vary; contact customer service for stock availability and estimated shipping dates.
• Documentation: CoA, SDS, and structural confirmation data (e.g., NMR, IR) may be available upon request.

For bulk quantities, custom packaging, or questions about product specifications, contact the Aladdin Scientific technical or sales team directly.

Frequently asked questions

What is the molecular formula and molecular weight of 1,2-Diformylhydrazine?

1,2-Diformylhydrazine has the molecular formula C₂H₄N₂O₂ and a molecular weight of 88.06 g/mol. The structure consists of a central hydrazine (–NH–NH–) unit with a formyl (–CHO) group attached to each nitrogen atom.

What are the main synthetic applications of 1,2-Diformylhydrazine?

1,2-Diformylhydrazine is used primarily as a bifunctional building block in heterocyclic synthesis (e.g., triazoles, oxadiazoles), as a precursor to bis-imine Schiff base ligands for coordination chemistry, and as a crosslinking unit in hydrazone-based dynamic covalent materials. Its dual formyl groups enable condensation with a wide range of amine-containing partners.

How should 1,2-Diformylhydrazine be stored to maintain its stability?

Store 1,2-Diformylhydrazine in a cool, dry, well-ventilated location, away from moisture, light, heat sources, and incompatible materials such as strong oxidisers and strong acids. For long-term storage, sealing the container under an inert atmosphere (nitrogen or argon) is recommended. Always refer to the SDS supplied with Aladdin SKU W135234 for full storage requirements.

Is 1,2-Diformylhydrazine soluble in common laboratory solvents?

Due to its hydrophilic formyl and hydrazine functional groups, 1,2-Diformylhydrazine is expected to show reasonable solubility in polar solvents such as water, methanol, and DMSO. Solubility in non-polar solvents such as hexane or toluene is anticipated to be low. Researchers should confirm solubility experimentally under their specific conditions.

What safety precautions should be taken when handling 1,2-Diformylhydrazine?

As a hydrazine derivative, 1,2-Diformylhydrazine should be handled with care. Wear appropriate PPE including nitrile gloves, safety glasses, and a lab coat. Perform all manipulations in a well-ventilated fume hood. Consult the Aladdin Scientific SDS for SKU W135234 for specific hazard classifications, first-aid measures, and disposal guidelines before use.

How can I obtain a Certificate of Analysis or Safety Data Sheet for Aladdin SKU W135234?

Certificates of Analysis (CoA) and Safety Data Sheets (SDS) for 1,2-Diformylhydrazine (SKU W135234) can be requested through the Aladdin Scientific website product page or by contacting customer service directly. Lot-specific CoA documents provide purity data and analytical characterisation relevant to your research requirements.

References

1. General reference: March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley. (for hydrazone and acylhydrazine reactivity context)
2. General reference: Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. Oxford University Press. (for imine/Schiff base formation and bifunctional reagents)
3. Aladdin Scientific product page for 1,2-Diformylhydrazine, SKU W135234. (Product specifications, CoA, SDS)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.