2-Methylfuran-3-carbonyl Chloride: Key Facts & FAQs
2-Methylfuran-3-carbonyl Chloride: Key Facts & FAQs
2-Methylfuran-3-carbonyl chloride is a reactive heterocyclic acyl chloride used as an acylating agent in organic synthesis, enabling the introduction of a 2-methylfuran-3-carbonyl moiety into target molecules.
- Chemical Name
- 2-Methylfuran-3-carbonyl chloride
- SKU
- M700381
- Functional Class
- Acyl chloride (acid chloride); heterocyclic reagent
- Core Reaction
- Friedel–Crafts acylation and nucleophilic acyl substitution with amines, alcohols, and other nucleophiles
- Moisture Sensitivity
- Highly moisture-sensitive; hydrolyzes rapidly in the presence of water to release HCl
- Recommended Storage
- Store under inert atmosphere (N₂ or Ar), in a cool, dry place away from moisture and incompatible materials
What Is 2-Methylfuran-3-carbonyl Chloride?
2-Methylfuran-3-carbonyl chloride is an acyl chloride derived from 2-methylfuran-3-carboxylic acid. It belongs to the class of heterocyclic acid chlorides, combining a furan ring substituted with a methyl group at the 2-position and a highly electrophilic carbonyl chloride group at the 3-position. The compound is a valuable building block in organic synthesis, providing a furanyl carbonyl unit that can be transferred to a wide variety of nucleophilic partners including amines, alcohols, and aromatic systems under Lewis acid catalysis.
The furan scaffold confers useful electronic and structural properties to synthetic targets, making 2-methylfuran-3-carbonyl chloride particularly relevant in the preparation of pharmaceuticals, agrochemicals, and specialty materials.
Chemical Properties and Reactivity
As an acyl chloride, 2-methylfuran-3-carbonyl chloride is highly electrophilic at the carbonyl carbon. It undergoes rapid nucleophilic acyl substitution reactions with a broad range of nucleophiles:
- Amines: React to form the corresponding furanyl amides (amide bond formation), often without added base for secondary amines, or with a mild base (e.g., triethylamine) for primary amines to neutralize the liberated HCl.
- Alcohols and phenols: React to yield furanyl esters; a base is generally required to drive the reaction and scavenge HCl.
- Water: Hydrolyzes readily to regenerate 2-methylfuran-3-carboxylic acid and HCl; strict exclusion of moisture is therefore essential.
- Aromatic compounds: Participate in Friedel–Crafts acylation in the presence of a Lewis acid catalyst (e.g., AlCl₃) to furnish aryl furanyl ketones.
The 2-methyl substituent on the furan ring provides moderate steric shielding adjacent to the carbonyl and slightly modulates ring electron density relative to unsubstituted furan-3-carbonyl chloride.
Safe Handling, Storage, and Waste Disposal
Hazard profile: 2-Methylfuran-3-carbonyl chloride is corrosive and moisture-sensitive. Hydrolysis generates hydrochloric acid (HCl), which is corrosive to skin, eyes, and the respiratory tract. Handle exclusively in a well-ventilated fume hood with appropriate personal protective equipment (PPE): nitrile or neoprene gloves, safety goggles, and a lab coat.
Storage: Store in tightly sealed containers under an inert atmosphere (nitrogen or argon) at cool temperatures (2–8 °C or as specified on the product label), away from water, protic solvents, bases, and oxidizing agents. Desiccants (molecular sieves or anhydrous calcium sulfate) may be used to protect against moisture ingress.
Waste disposal: Carefully quench residual acyl chloride by slow addition to excess dilute aqueous base (e.g., dilute NaOH or Na₂CO₃ solution) in a fume hood before disposal. Dispose of all waste in accordance with applicable local, regional, and national regulations for corrosive and halogen-containing chemical waste.
Typical Laboratory Applications
2-Methylfuran-3-carbonyl chloride finds application in several synthetic contexts:
- Amide synthesis: Coupling with primary or secondary amines to produce furanyl amides, which are common pharmacophores and intermediates in medicinal chemistry programs.
- Ester synthesis: Reaction with alcohols or phenols under mild conditions to generate esters for use as protecting groups, prodrug moieties, or functional monomers.
- Ketone synthesis via Friedel–Crafts acylation: Generation of aryl or heteroaryl ketones bearing the 2-methylfuran-3-yl carbonyl motif, useful in the construction of biologically active scaffolds.
- Total synthesis and fragment coupling: Introduction of the 2-methylfuranyl carbonyl handle at a late synthetic stage, leveraging its high reactivity toward nucleophiles to forge key bonds efficiently.
Always optimize reaction conditions (solvent, temperature, stoichiometry of base) in small-scale pilot experiments before scale-up.
Ordering, Specification, and Quality
Aladdin Scientific supplies 2-Methylfuran-3-carbonyl chloride under SKU M700381. When placing an order or evaluating specifications, consider the following:
- Purity: Confirm the purity grade stated on the Certificate of Analysis (CoA) for your intended application; higher-purity material is generally preferred for sensitive synthetic steps.
- Packaging: Request inert-atmosphere sealed packaging to preserve reagent quality during shipping and storage.
- Documentation: A CoA, Safety Data Sheet (SDS/MSDS), and, where available, NMR/GC data should accompany each lot. Contact Aladdin Scientific technical support for lot-specific documentation.
- Quantities: Available in research quantities; contact the sales team for bulk pricing or custom packaging options.
For procurement questions, custom synthesis inquiries, or technical support, please contact Aladdin Scientific customer service directly.
Frequently asked questions
What nucleophiles react well with 2-Methylfuran-3-carbonyl chloride?
Primary and secondary amines react readily to form amides, typically in the presence of a mild base such as triethylamine to neutralize the HCl by-product. Alcohols and phenols react to give esters under similar conditions. Aromatic compounds can be acylated via Friedel–Crafts conditions using a Lewis acid catalyst such as AlCl₃.
How should I handle 2-Methylfuran-3-carbonyl chloride safely in the laboratory?
Always handle this reagent in a well-ventilated fume hood while wearing nitrile or neoprene gloves, safety goggles, and a lab coat, as it is corrosive and moisture-sensitive. Avoid exposure to water, protic solvents, and bases during weighing and transfer operations. In case of skin or eye contact, flush immediately with copious amounts of water and seek medical attention.
What are the recommended storage conditions for 2-Methylfuran-3-carbonyl chloride?
Store tightly sealed under an inert atmosphere (nitrogen or argon) in a cool, dry location (typically 2–8 °C or as indicated on the product label), away from moisture, protic solvents, and incompatible materials such as strong bases and oxidizers. Desiccants may be used to prevent moisture ingress during storage.
How do I quench excess 2-Methylfuran-3-carbonyl chloride after a reaction?
In a fume hood, slowly add the residual acyl chloride (or reaction mixture) to a large excess of dilute aqueous base, such as dilute sodium hydroxide or sodium carbonate solution. This hydrolyzes the acyl chloride and neutralizes the liberated HCl. Dispose of the resulting waste according to local regulations for corrosive and halogen-containing materials.
What solvents are compatible with 2-Methylfuran-3-carbonyl chloride?
Anhydrous aprotic solvents such as dichloromethane (DCM), tetrahydrofuran (THF), toluene, and diethyl ether are commonly used with acyl chlorides of this type. Protic solvents (water, methanol, ethanol) must be strictly avoided as they react rapidly with the acyl chloride, causing hydrolysis or solvolysis and consuming the reagent unproductively.
References
- March, J.; Smith, M. B. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th ed.; Wiley: Hoboken, NJ, 2013. (General acyl chloride reactivity and nucleophilic acyl substitution)
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Acid chloride chemistry, amide and ester formation)
- Aladdin Scientific Product Page: 2-Methylfuran-3-carbonyl chloride, SKU M700381. (Product specifications and safety information)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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