5-Bromofuran-2-carbohydrazide: Properties, Uses & Lab Guide

5-Bromofuran-2-carbohydrazide is a halogenated furan-based acylhydrazide building block widely employed in medicinal chemistry and heterocyclic synthesis for the preparation of bioactive compounds and pharmaceutical intermediates.

CAS Number

Need verification — review flag raised

Molecular Formula

C5H5BrN2O2

Molecular Weight

205.01 g/mol (calculated; needs verification)

Functional Groups

Acylhydrazide (–CO–NH–NH2) and aryl bromide on furan ring

Primary Applications

Synthesis of hydrazones, diazines, triazoles, and other N-heterocycles; pharmaceutical intermediate

Storage Conditions

Store in a cool, dry, well-ventilated place away from light (verify with SDS)

SKU

B697807

Chemical Identity and Structure

5-Bromofuran-2-carbohydrazide is an acylhydrazide derivative of 5-bromofuran-2-carboxylic acid. Its structure combines three key features: a furan aromatic ring, a bromine substituent at the 5-position, and a carbohydrazide (–CO–NH–NH2) group at the 2-position.

The presence of both the electrophilic bromine atom and the nucleophilic hydrazide moiety makes this compound a bifunctional building block of significant synthetic utility. The furan ring imparts planarity and contributes to π–π stacking interactions relevant in drug–target binding. The C–Br bond is amenable to palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig), while the hydrazide terminus participates readily in condensation reactions with carbonyl compounds to form hydrazones and related heterocycles.

Molecular Formula: C5H5BrN2O2 | Molecular Weight: ~205.01 g/mol (needs verification against certificate of analysis).

Synthetic Applications in Medicinal and Organic Chemistry

5-Bromofuran-2-carbohydrazide serves as a versatile intermediate in the construction of nitrogen-rich heterocyclic frameworks that are prevalent in pharmaceutical candidates. Key reaction pathways include:

• Hydrazone formation: Condensation with aldehydes or ketones yields acylhydrazones, which themselves display a range of biological activities including antimicrobial, antifungal, and anticancer properties.
• Cyclization to 1,3,4-oxadiazoles and 1,2,4-triazoles: Reaction with carboxylic acid derivatives, acid chlorides, or orthoesters followed by cyclodehydration produces five-membered heterocycles widely explored in drug discovery programs.
• Palladium-catalyzed cross-coupling: The aryl bromide handle enables Suzuki–Miyaura, Negishi, and Stille couplings to diversify the furan scaffold, generating biaryl or heteroaryl analogue libraries.
• Schiff base synthesis: The –NH–NH2 terminus condenses with aromatic aldehydes to give Schiff bases of pharmacological interest.

These orthogonal reactivities allow medicinal chemists to use 5-Bromofuran-2-carbohydrazide for rapid library synthesis and structure–activity relationship (SAR) studies.

Handling, Safety, and Storage Guidelines

As with all laboratory reagents containing an aryl halide and a reactive hydrazide group, appropriate precautions should be observed when working with 5-Bromofuran-2-carbohydrazide:

• Personal Protective Equipment (PPE): Wear nitrile gloves, safety glasses, and a lab coat. Work in a fume hood to avoid inhalation of dust or vapors.
• Storage: Store in a tightly sealed container in a cool (typically 2–8 °C or room temperature per SDS), dry location away from direct light and incompatible oxidizing agents. Verify exact storage conditions on the product SDS and certificate of analysis.
• Stability: Hydrazide compounds can be sensitive to prolonged exposure to moisture and air; minimize repeated opening of the container.
• Disposal: Dispose of waste in accordance with local institutional and governmental regulations for halogenated organic compounds.

Note: Always consult the Safety Data Sheet (SDS) supplied with the product before use. The above guidelines are general and do not substitute for the product-specific SDS.

Analytical Characterization and Quality Specifications

Researchers procuring 5-Bromofuran-2-carbohydrazide should request or review the certificate of analysis (CoA) for the following key quality parameters:

• Purity: Typically assessed by HPLC or GC; pharmaceutical-grade synthetic work commonly requires ≥95% purity. Verify the specific purity grade offered by Aladdin Scientific for SKU B697807.
• Identity confirmation: 1H NMR and 13C NMR spectra should confirm the acylhydrazide protons (broad N–H signals) and the two furan ring protons; mass spectrometry (ESI-MS) should show the characteristic isotope pattern of a mono-brominated compound (M and M+2 peaks in approximately 1:1 ratio).
• Melting point: A sharp, reproducible melting point serves as an additional purity indicator (specific value needs verification from CoA).
• Appearance: Typically a white to off-white or pale yellow solid (verify against CoA).

For critical applications such as lead optimization or regulatory submission work, in-house re-characterization by NMR and HRMS is strongly recommended.

Frequently asked questions

What is 5-Bromofuran-2-carbohydrazide primarily used for in research?

It is primarily used as a bifunctional building block in medicinal and organic chemistry. The hydrazide group participates in condensation reactions to form hydrazones, 1,3,4-oxadiazoles, and triazoles, while the aryl bromide enables palladium-catalyzed cross-coupling reactions for scaffold diversification.

How should 5-Bromofuran-2-carbohydrazide be stored to ensure stability?

Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area away from direct light and moisture. Because hydrazide groups can be sensitive to moisture and air, minimize repeated opening of the container. Always verify the specific storage conditions on the product SDS and CoA.

What analytical methods confirm the identity and purity of 5-Bromofuran-2-carbohydrazide?

Purity is routinely assessed by HPLC or GC. Structural identity is confirmed by 1H and 13C NMR (characteristic N–H signals of the hydrazide and furan ring protons) and by mass spectrometry, which shows the diagnostic 1:1 isotope doublet of a mono-brominated compound. Melting point determination provides an additional purity check.

Can 5-Bromofuran-2-carbohydrazide undergo Suzuki coupling reactions?

Yes. The aryl C–Br bond on the furan ring is compatible with palladium-catalyzed Suzuki–Miyaura cross-coupling with arylboronic acids, enabling introduction of diverse aryl or heteroaryl groups. Reaction conditions should be optimized for the sensitivity of the hydrazide moiety to strongly basic or high-temperature conditions.

What purity grade is available for SKU B697807 from Aladdin Scientific?

The specific purity grade for B697807 should be confirmed directly on the Aladdin Scientific product page or certificate of analysis. For synthetic research applications, a purity of ≥95% is commonly required and should be verified prior to purchase.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for hydrazide reactivity and heterocycle formation.
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed. Oxford University Press. Reference for acylhydrazide condensation chemistry and Schiff base formation.
3. Kaur, R. et al. Hydrazide-hydrazones as potential antimicrobial and anticancer agents: A review. European Journal of Medicinal Chemistry (general reference — specific volume and page need verification).
4. Aladdin Scientific. Product page for 5-Bromofuran-2-carbohydrazide, SKU B697807. Aladdin Scientific official website.

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