1-(2-Furfuryl)-2-Thiourea: Properties, Uses & Lab Guide

1-(2-Furfuryl)-2-thiourea is a furan-containing thiourea derivative that serves as a versatile building block in heterocyclic synthesis and coordination chemistry research.

Chemical Name

1-(2-Furfuryl)-2-thiourea

Molecular Formula

C6H8N2OS

Molecular Weight

156.20 g/mol

Functional Class

Thiourea / Furan derivative

CAS Number

Needs review — not confirmed in source material

Primary Application

Building block in heterocyclic and medicinal chemistry synthesis

Storage Condition

Store in a cool, dry place away from light (specific conditions need review)

Chemical Structure and Key Properties

1-(2-Furfuryl)-2-thiourea belongs to the thiourea family of organosulfur compounds, distinguished by the presence of a 2-furfuryl substituent on one nitrogen atom of the thiourea core (–NH–C(=S)–NH₂). The furfuryl group introduces a five-membered aromatic furan ring, which significantly influences the compound's electronic properties, hydrogen-bonding capacity, and reactivity.

Thioureas in general are characterized by the C=S (thione) functional group flanked by two nitrogen atoms. This arrangement confers strong hydrogen-bond donor ability at the N–H positions and makes the sulfur atom an effective ligand donor in coordination complexes. The integration of the furan ring adds π-conjugation and offers additional coordination or reactivity sites in synthetic transformations.

The molecular formula is C₆H₈N₂OS, giving a molecular weight of approximately 156.20 g/mol. The compound is expected to be a solid at room temperature, consistent with related furfuryl thiourea analogues, though researchers should verify specific physical constants such as melting point against the certificate of analysis supplied with each lot.

Synthesis Relevance and Reactivity

Thiourea derivatives bearing N-furfuryl substituents are recognized intermediates in the preparation of biologically and pharmaceutically relevant heterocyclic scaffolds. The thiourea moiety can undergo cyclization reactions with electrophilic carbonyl compounds, alpha-halo ketones, or other bifunctional reagents to afford thiazolines, thiazolidinones, aminothiazoles, and related ring systems. The furan ring may participate in Diels–Alder reactions under appropriate conditions, broadening the synthetic utility of this compound.

The N–H groups also make 1-(2-Furfuryl)-2-thiourea a candidate for use in organocatalysis, where chiral or achiral thiourea catalysts activate electrophiles through dual hydrogen-bond donation. Additionally, the sulfur lone pairs enable coordination to transition metals, making this compound of interest in the preparation of metal complexes for catalytic or materials science applications.

Researchers working with this reagent should employ standard handling procedures for thiourea compounds: avoid prolonged exposure to moisture and strong oxidizing agents, and conduct reactions under inert atmosphere when air-sensitive intermediates are involved.

Laboratory Handling, Storage, and Safety

As with most thiourea compounds, 1-(2-Furfuryl)-2-thiourea should be handled with appropriate personal protective equipment including nitrile gloves, laboratory coat, and safety glasses. The compound should be weighed in a well-ventilated fume hood to minimize inhalation of fine particulates.

For storage, keep the reagent in a tightly sealed container in a cool (typically 2–8 °C or room temperature as specified on the product label), dry, and dark environment to prevent decomposition or discoloration. Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific prior to use for authoritative hazard classification, first-aid measures, and disposal guidance specific to this compound.

Incompatibilities typical of thiourea reagents include strong oxidizers, strong acids, and reactive halogenating agents. Decomposition products may include sulfur oxides and nitrogen oxides; therefore, waste should be disposed of in accordance with local regulations for organosulfur compounds.

Applications in Research

1-(2-Furfuryl)-2-thiourea finds application across several research domains:

• Medicinal Chemistry: Thiourea-furfuryl hybrids have been explored as pharmacophores in the design of antimicrobial, antifungal, and antiparasitic agents, leveraging the established bioactivity profile of both the thiourea and furan pharmacophoric units.
• Coordination Chemistry: The compound can act as an S- or N-donor ligand toward transition and heavy metal ions, facilitating the preparation of novel coordination complexes with potential catalytic or luminescent properties.
• Organic Synthesis: Used as a building block for the construction of thiazolinone, aminothiazole, and related heterocyclic ring systems through condensation and cyclization strategies.
• Organocatalysis: Achiral thiourea scaffolds can serve as hydrogen-bond donor catalysts for a variety of asymmetric or non-asymmetric transformations.

Researchers are encouraged to review the primary literature for protocols optimized for this specific compound, as reaction conditions may differ from those reported for simpler thiourea analogues.

Frequently asked questions

What is 1-(2-Furfuryl)-2-thiourea used for in organic synthesis?

1-(2-Furfuryl)-2-thiourea serves as a versatile building block for the synthesis of heterocyclic compounds such as aminothiazoles, thiazolinones, and related ring systems via condensation with carbonyl or alpha-halo compounds. It can also act as a ligand in coordination chemistry and as a hydrogen-bond donor in organocatalytic applications.

How should 1-(2-Furfuryl)-2-thiourea be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool, dry, and dark environment, away from moisture, strong oxidizers, and direct light. Consult the product label and the Aladdin Scientific SDS for lot-specific storage temperature recommendations.

Is 1-(2-Furfuryl)-2-thiourea suitable for use as a metal-chelating ligand?

Yes, the sulfur and nitrogen donor atoms in the thiourea moiety, combined with the oxygen of the furan ring, give 1-(2-Furfuryl)-2-thiourea potential as a chelating or bridging ligand toward transition and heavy metals. The specific coordination mode will depend on the metal ion and reaction conditions employed.

What safety precautions should be taken when handling this compound?

Use personal protective equipment including nitrile gloves, a laboratory coat, and safety glasses. Handle in a well-ventilated fume hood. Avoid contact with strong oxidizing agents and consult the SDS for full hazard information, first-aid procedures, and waste disposal requirements.

What is the molecular formula and molecular weight of 1-(2-Furfuryl)-2-thiourea?

1-(2-Furfuryl)-2-thiourea has the molecular formula C6H8N2OS and a molecular weight of approximately 156.20 g/mol. Researchers should confirm exact values against the certificate of analysis provided with each lot.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for thiourea chemistry.
2. Kaur, R. et al. Thiourea derivatives in medicinal chemistry: a review. General literature reference — specific article details need verification.
3. Aladdin Scientific. Product page for 1-(2-Furfuryl)-2-thiourea, SKU T698800.

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