What Is Methyl 1-(3-Bromophenyl)cyclopropane-1-Carboxylate?

Methyl 1-(3-bromophenyl)cyclopropane-1-carboxylate (SKU M692600) is an organic compound combining three chemically distinct motifs: a strained cyclopropane ring, a meta-substituted aryl bromide, and a methyl ester group. Its molecular formula is C₁₁H₁₁BrO₂. The quaternary carbon at the cyclopropane C-1 position bears both the aryl group and the ester, imparting conformational rigidity that is increasingly exploited in drug design to improve selectivity and reduce metabolic liability. The meta-bromophenyl moiety serves as a versatile handle for palladium- and nickel-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Negishi, and Buchwald–Hartwig couplings.

How Should This Compound Be Stored and Handled?

As with most aryl bromide esters, Methyl 1-(3-bromophenyl)cyclopropane-1-carboxylate should be stored in a cool, dry, well-ventilated area away from moisture and incompatible oxidizing agents. Sealed containers under an inert atmosphere (nitrogen or argon) are recommended to prevent slow hydrolysis of the ester functionality over extended storage periods. Standard laboratory personal protective equipment—including nitrile gloves, safety glasses, and a lab coat—should be worn when handling this material. Consult the Safety Data Sheet (SDS) supplied with product M692600 for specific hazard classifications and first-aid measures before use.

What Are the Key Synthetic Applications?

This compound serves as a privileged building block in several synthetic contexts:

• Cross-coupling chemistry: The aryl C–Br bond undergoes efficient Suzuki–Miyaura coupling with boronic acids, Negishi coupling with organozinc reagents, and Buchwald–Hartwig amination, enabling rapid diversification of the aryl ring.
• Ester elaboration: The methyl ester can be hydrolyzed to the corresponding carboxylic acid, reduced to the alcohol, converted to an amide, or used in Claisen-type condensations, providing multiple downstream structural options.
• Cyclopropane ring opening or functionalization: Under appropriate conditions, the strained ring can participate in ring-opening reactions, expanding the accessible chemical space for library synthesis.
• Medicinal chemistry scaffold: The 1-arylcyclopropane-1-carboxylate motif is found in bioactive molecules and serves as a bioisostere for certain amino acid-derived scaffolds.

Researchers in drug discovery, agrochemical research, and materials science will find this compound particularly useful as an entry point to structurally diverse analogue libraries.

How Do I Order and What Quality Can I Expect?

Methyl 1-(3-bromophenyl)cyclopropane-1-carboxylate is available from Aladdin Scientific under SKU M692600. To place an order, visit the Aladdin Scientific website, search by SKU or product name, select the desired quantity, and proceed through the standard checkout process. For bulk quantities or custom packaging, contact our sales team directly.

Aladdin Scientific applies rigorous quality control to research reagents, typically including purity verification by GC or HPLC and structural confirmation by NMR or MS. Specific purity data and certificates of analysis (CoA) are available upon request or via the product page. If you have questions about reagent grade suitability for your specific assay or synthesis, our technical support team can advise.