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Description
4-Guanidinobenzoic Acid Methanesulfonate is the methanesulfonate salt of 4-guanidinobenzoic acid, an aromatic compound carrying a strongly basic guanidine group positioned para to a carboxylate group. This combination of two functional groups with opposing character makes it an attractive building block in medicinal chemistry, particularly for assembling molecules that need to interact with negatively charged binding pockets on proteins. The methanesulfonate salt form is chosen because it yields a solid that is considerably easier to handle and weigh out accurately than the free base, which matters a great deal in routine synthetic laboratory work.
The property that makes this material a frequent choice is the guanidine group, which remains protonated across the physiological pH range and therefore produces a stable delocalized cation capable of forming strong paired hydrogen bonds. The aromatic carboxylate group remains available for esterification or amidation, so the compound can be coupled onto other molecular fragments as a recognition element. The methanesulfonate salt form generally improves solubility in polar solvents and in water compared with the free zwitterionic form, which assists in preparing stock solutions and in purifying reaction products. The solid is also stable in storage.
In Indonesian laboratories, this building block is typically found in university medicinal chemistry groups, pharmaceutical research and development units, and contract synthesis facilities working on protease-directed or cation-recognition scaffolds. It is normally ordered in small research quantities, weighed out on an analytical balance, and dissolved for coupling reactions or for preparing stock solutions. Its solid, easily handled salt form suits laboratories that work in warm and humid ambient conditions, where free bases are harder to manage reliably.
Laboratory Applications
Medicinal chemistry building block synthesis: the para-arranged guanidine and carboxylate groups let chemists construct target molecules that need a permanently charged recognition element at a defined geometric position.
Protein binding pocket targeting studies: the delocalized guanidinium cation forms strong paired hydrogen bonds with negatively charged residues, making it useful for designing ligands aimed at anionic binding sites.
Amide coupling and fragment assembly: the free aromatic carboxylate group is available for amidation, allowing this compound to be joined onto larger molecular fragments as a recognition unit.
Esterification reactions for derivative preparation: the carboxylate group can be esterified to generate analogue series while the guanidine group retains its basic character throughout the transformation.
Aqueous stock solution preparation: improved solubility in polar and aqueous solvents compared with the free zwitterionic form makes accurate stock solutions straightforward to prepare and dispense.
Specifications
Brand: TCI
CAS Number: 148720-07-4
Product Code: G0248
Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Physical Form: solid (methanesulfonate salt)
Pack Sizes: available in standard TCI research pack sizes; please confirm the size required when ordering
Storage: store the solid under stable, dry conditions
Handling and Storage
Store the solid in a tightly closed original container in a cool, dry place away from moisture and direct sunlight, since ambient humidity in many Indonesian laboratories can affect solid handling. Amber glass or the manufacturer's supplied container is suitable; keep the cap sealed between weighings and allow the container to reach room temperature before opening to limit condensation. Handle the powder in a fume hood or well-ventilated area using gloves, safety glasses, and a laboratory coat, and avoid generating or inhaling dust. Weigh with clean, dry spatulas to prevent cross-contamination, label all prepared solutions clearly, and consult the manufacturer's safety data sheet before first use and before disposal.
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