What Is 2-Methylfuran-3-carbonyl Chloride?

2-Methylfuran-3-carbonyl chloride (SKU M700381) is an acyl chloride derived from the furan ring system, bearing a methyl substituent at the 2-position and a carbonyl chloride (–COCl) group at the 3-position. It belongs to the class of heterocyclic acid chlorides, which are highly valued in medicinal chemistry and material science as versatile electrophilic acylating agents. The compound enables the introduction of a 2-methylfuran-3-carbonyl moiety into target molecules through acylation of amines, alcohols, and related nucleophiles.

Chemical Properties and Handling

As an acyl chloride, 2-methylfuran-3-carbonyl chloride is highly moisture-sensitive. Exposure to water or atmospheric humidity results in rapid hydrolysis to the corresponding carboxylic acid (2-methylfuran-3-carboxylic acid) and hydrogen chloride gas. It should therefore be handled exclusively in a dry, inert-atmosphere environment (e.g., under nitrogen or argon) using Schlenk techniques or a glove box when prolonged exposure is anticipated.

It reacts vigorously with amines to form amides and with alcohols to form esters, making it a powerful acylation tool. Appropriate personal protective equipment (PPE) — including chemical-resistant gloves, lab coat, and eye protection — must be worn at all times. All manipulations should be conducted in a well-ventilated fume hood due to the potential release of HCl.

Storage and Stability

2-Methylfuran-3-carbonyl chloride should be stored in tightly sealed containers under an inert gas blanket (nitrogen or argon) at cool temperatures, away from moisture, heat sources, and incompatible materials such as bases, alcohols, and water. Proper storage in a dedicated flammable/corrosive reagent cabinet is recommended. Under appropriate dry conditions, acyl chlorides of this type typically maintain acceptable stability; however, specific shelf-life data for this product should be confirmed with Aladdin Scientific's technical support team.

Applications in Organic Synthesis

The 2-methylfuran-3-carbonyl chloride scaffold is useful in several synthetic contexts:

• Amide bond formation: Reaction with primary or secondary amines under mild conditions (typically with a base such as triethylamine to scavenge HCl) provides furan-containing amides useful in drug discovery and agrochemical research.
• Ester synthesis: Acylation of alcohols yields esters incorporating the 2-methylfuran-3-carbonyl group, which may serve as protecting groups, prodrug linkages, or functional monomers.
• Friedel–Crafts acylation: In the presence of a Lewis acid catalyst, the compound can participate in Friedel–Crafts-type reactions to introduce acyl groups onto aromatic or heteroaromatic substrates.

Its heterocyclic furan core also imparts bioisosteric properties that are of interest in medicinal chemistry programs targeting improved pharmacokinetic profiles.

Ordering and Technical Support

2-Methylfuran-3-carbonyl chloride is available from Aladdin Scientific under SKU M700381. For questions regarding pricing, availability, custom quantities, certificate of analysis (CoA), safety data sheets (SDS), or technical specifications, please contact Aladdin Scientific's customer service or technical support team directly through the website. Bulk and custom synthesis inquiries are also welcome.