2-Chloro-5-phenyl-1,3,4-oxadiazole: Properties & Lab Use
2-Chloro-5-phenyl-1,3,4-oxadiazole: Properties & Lab Use
2-Chloro-5-phenyl-1,3,4-oxadiazole is a reactive heterocyclic building block widely employed in medicinal and synthetic chemistry as an electrophilic intermediate for constructing diverse 1,3,4-oxadiazole-containing compounds with potential biological activity.
- Chemical Name
- 2-Chloro-5-phenyl-1,3,4-oxadiazole
- SKU / Catalog Number
- C191025
- Molecular Formula
- C8H5ClN2O
- Molecular Weight
- 180.59 g/mol
- Core Structure
- 1,3,4-Oxadiazole ring with chloro substituent at C-2 and phenyl group at C-5
- Primary Application
- Electrophilic building block for nucleophilic substitution and cross-coupling in heterocyclic synthesis
What Is 2-Chloro-5-phenyl-1,3,4-oxadiazole?
2-Chloro-5-phenyl-1,3,4-oxadiazole (CAS catalog SKU C191025) is an aromatic heterocyclic compound featuring a five-membered 1,3,4-oxadiazole ring. The ring contains one oxygen atom and two nitrogen atoms at the 1, 3, and 4 positions. A chlorine atom at the 2-position acts as an excellent leaving group, making this molecule highly reactive toward nucleophiles such as amines, thiols, and alkoxides. A phenyl group at the 5-position provides electronic stabilization and a handle for further derivatization.
The 1,3,4-oxadiazole scaffold is recognized in medicinal chemistry for its metabolic stability, bioisosteric relationship with ester and amide bonds, and documented association with antimicrobial, antifungal, anticancer, and anti-inflammatory activities in the literature. As a consequence, 2-chloro-5-phenyl-1,3,4-oxadiazole serves as a key electrophilic intermediate for rapid library synthesis of bioactive candidates.
Physicochemical Properties and Handling
2-Chloro-5-phenyl-1,3,4-oxadiazole has the molecular formula C8H5ClN2O and a molecular weight of approximately 180.59 g/mol. The compound typically presents as a white to off-white crystalline solid at room temperature. Its aromatic and heteroaromatic character confers moderate lipophilicity, and it is generally soluble in common organic solvents such as dichloromethane, chloroform, dimethyl sulfoxide (DMSO), acetonitrile, and ethyl acetate, while being sparingly soluble in water.
Because of the reactive C–Cl bond, the compound should be stored in a cool, dry, well-ventilated location away from moisture, strong nucleophiles, and bases. Handling under inert atmosphere (nitrogen or argon) is advisable when moisture-sensitive reactions are performed. Standard laboratory personal protective equipment—gloves, safety glasses, and a laboratory coat—must be worn. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use.
Synthetic Applications in Medicinal and Organic Chemistry
The most exploited reaction of 2-chloro-5-phenyl-1,3,4-oxadiazole is nucleophilic aromatic substitution (SNAr) at the electron-deficient C-2 position. Amines react smoothly to yield 2-amino-5-phenyl-1,3,4-oxadiazole analogs; thiols give the corresponding thioether derivatives; and alkoxides afford alkoxy-substituted products. These transformations are generally conducted under mild conditions (room temperature to 80 °C) in polar aprotic solvents such as DMSO or acetonitrile, typically in the presence of a base such as triethylamine or potassium carbonate.
The compound also participates in transition-metal-catalyzed cross-coupling reactions, including Suzuki–Miyaura and Buchwald–Hartwig protocols, when the chloro leaving group is utilized in palladium-catalyzed processes. This versatility makes C191025 a valuable reagent for constructing structurally diverse heterocyclic libraries for drug discovery, materials science (e.g., organic light-emitting diodes), and agrochemical research.
Ordering, Availability, and Storage at Aladdin Scientific
2-Chloro-5-phenyl-1,3,4-oxadiazole is available from Aladdin Scientific under SKU C191025. Customers can place orders directly through the Aladdin Scientific website, by contacting our sales team, or via approved procurement platforms. Volume pricing and bulk quantities may be available upon request; please contact our sales department for a custom quotation.
For long-term storage, keep the product sealed in its original container under cool (2–8 °C or room temperature as specified on the product label), dry conditions away from light and incompatible materials. Always verify current stock, purity specifications, and Certificate of Analysis (CoA) data on the product page before ordering. If you have questions about shipping, hazard classification, or export compliance for this reagent, please contact Aladdin Scientific customer service.
Frequently asked questions
What nucleophiles react with 2-Chloro-5-phenyl-1,3,4-oxadiazole?
Primary and secondary amines, thiols, and alkoxides are among the most common nucleophiles used in SNAr reactions with this compound, displacing the chloro group at C-2 under mild to moderate conditions. Palladium-catalyzed coupling partners such as arylboronic acids and aryl amines can also react via cross-coupling protocols.
What solvents are recommended for reactions using 2-Chloro-5-phenyl-1,3,4-oxadiazole?
Polar aprotic solvents such as DMSO, acetonitrile, and DMF are generally recommended for SNAr reactions because they stabilize the anionic transition state without interfering with the nucleophile. Dichloromethane and THF are also used depending on the reaction type and the reagents involved.
How should 2-Chloro-5-phenyl-1,3,4-oxadiazole be stored to maintain stability?
The compound should be stored in a tightly sealed container under cool, dry conditions, protected from moisture and light. Refrigeration (2–8 °C) is advisable for extended shelf life. Verify storage conditions on the product label or Certificate of Analysis provided with the shipment from Aladdin Scientific.
What is the molecular weight and formula of 2-Chloro-5-phenyl-1,3,4-oxadiazole?
The molecular formula is C8H5ClN2O and the molecular weight is approximately 180.59 g/mol. Always confirm exact values against the Certificate of Analysis supplied with your specific lot from Aladdin Scientific (SKU C191025).
Can 2-Chloro-5-phenyl-1,3,4-oxadiazole be used in palladium-catalyzed cross-coupling reactions?
Yes, the C–Cl bond can serve as the electrophilic partner in palladium-catalyzed reactions such as Suzuki–Miyaura coupling and Buchwald–Hartwig amination, although aryl chlorides are generally less reactive than aryl bromides or iodides and may require more active catalyst systems or elevated temperatures.
References
- Textbook knowledge: March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Smith, M. B.; March, J. Wiley-Interscience. General reference for SNAr reactions and heterocyclic chemistry.
- General reference for 1,3,4-oxadiazole medicinal chemistry applications: Kumar, D. et al. 1,3,4-Oxadiazole: A biologically active scaffold in drug discovery — a review of the literature. No specific article confirmed; flag for verification.
- Aladdin Scientific product page for 2-Chloro-5-phenyl-1,3,4-oxadiazole, SKU C191025. www.aladdin-e.com
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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