3-(Methoxycarbonyl)bicyclo[111]pentane-1-carboxylic Acid TCI M3149

TCI M3149 3-(Methoxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic Acid is a rigid, angular building block that has become one of the most sought-after scaffolds in modern medicinal chemistry. The bicyclo[1.1.1]pentane core is widely recognised as a bioisostere of the benzene ring, meaning a structural replacement that preserves the distance between two substituents while changing the molecular shape from flat to genuinely three-dimensional. The compound is supplied as a monoester, carrying a free carboxylic acid at one end and a methyl ester at the other, which allows chemists to work on the two termini separately and under full control.

What makes this material distinctive is that the functional group differentiation is already built in from the outset. The free carboxylic acid is immediately available for amidation, Curtius rearrangement, or reduction, while the methyl ester remains protected until it is hydrolysed at a later stage of the sequence. The rigidity of the bicyclo[1.1.1]pentane framework suppresses conformational degrees of freedom, so the entropic penalty of binding to a biological target becomes more favourable. Replacing an aromatic ring with this scaffold also generally improves aqueous solubility and lowers lipophilicity.

In Indonesian laboratories, this building block is typically used in medicinal chemistry and synthetic organic research groups pursuing scaffold-hopping and lead-optimisation work, where a flat aromatic ring is deliberately exchanged for a three-dimensional equivalent. It is handled on small to moderate scale in university research laboratories, pharmaceutical R&D units, and contract synthesis facilities, where the pre-differentiated acid and ester termini let a multi-step route be planned without additional protecting group manipulation.

• Benzene ring bioisostere replacement: the bicyclo[1.1.1]pentane core maintains the substituent-to-substituent distance of a para-phenylene unit while converting a flat aromatic motif into a three-dimensional framework.
• Stepwise bidirectional functionalisation: the free carboxylic acid and the methyl ester allow two different reactions to be performed sequentially at opposite ends of the same molecule under controlled conditions.
• Amide coupling and peptidomimetic construction: the free carboxylic acid terminus is directly available for amidation, letting the rigid scaffold be inserted into an amide-linked chain without prior deprotection steps.
• Curtius rearrangement to bridgehead amines: the free acid can be converted into the corresponding amine, giving access to differentiated amino-ester intermediates built on the rigid bicyclopentane core.
• Lead optimisation for solubility and lipophilicity tuning: exchanging an aromatic ring for this scaffold generally raises aqueous solubility and lowers lipophilicity in the resulting analogue series.

• Product code: M3149

Store the container tightly closed in a cool, dry, well-ventilated area, away from direct sunlight, heat sources, and incompatible materials such as strong bases and strong oxidising agents. Keep the compound in its original tightly sealed glass or manufacturer-supplied container, and reseal promptly after weighing to limit moisture uptake. Handle the material inside a fume hood while wearing safety goggles, chemical-resistant gloves, and a laboratory coat. As a carboxylic acid, it may irritate the skin, eyes, and respiratory tract, so avoid dust formation and direct contact. Always consult the manufacturer's safety data sheet before use, and dispose of residues and contaminated materials through the laboratory's chemical waste procedures.

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