(S)-Oxetan-2-ylmethanamine tsoh
[CAS# 2740593-38-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Tosylate
• Name: (S)-Oxetan-2-ylmethanamine tsoh
• Synonyms: 4-methylbenzenesulfonic acid;[(2S)-oxetan-2-yl]methanamine
• Molecular Formula: C₁₁H₁₇NO₄S
• Molecular Weight: 259.32
• CAS Registry Number: 2740593-38-6
• SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.C1CO[C@@H]1CN

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+P351+P351-P302+P352

Discovory and Applicatios

(S)-Oxetan-2-ylmethanamine p-toluenesulfonate (commonly abbreviated as (S)-Oxetan-2-ylmethanamine TsOH) is a salt formed between the chiral primary amine (S)-oxetan-2-ylmethanamine and p-toluenesulfonic acid (TsOH). This compound is a valuable building block in medicinal chemistry and organic synthesis due to its combination of chirality, strained ring structure, and functional groups.

The (S)-oxetan-2-ylmethanamine component features a four-membered oxetane ring substituted at the 2-position with a chiral center bearing a methylamine side chain. Oxetanes are small, oxygen-containing rings that are known for their high ring strain and unique physicochemical properties. Their inclusion in drug design can modulate molecular polarity, improve metabolic stability, and serve as bioisosteres for carbonyl or gem-dimethyl groups.

The (S)-enantiomer of oxetan-2-ylmethanamine is especially significant in chiral synthesis, as stereochemistry often influences binding affinity, selectivity, and the pharmacokinetic profile of active pharmaceutical ingredients. The primary amine group offers a site for further derivatization, such as amide or urea formation, which makes this compound versatile in generating a broad array of analogs or conjugates.

The p-toluenesulfonic acid salt form enhances the compound's stability and solubility in polar solvents. Salt formation is a common technique in pharmaceutical development to improve the handling, crystallinity, and sometimes even the bioavailability of a compound. TsOH is a strong organic acid that forms crystalline salts with basic amines, which can facilitate purification and characterization.

(S)-Oxetan-2-ylmethanamine TsOH has found application in the synthesis of biologically active molecules, particularly in research exploring CNS agents, enzyme inhibitors, and fragments for fragment-based drug design. The oxetane ring is known to influence lipophilicity and reduce undesired metabolic transformations, particularly those involving aromatic oxidation or N-dealkylation, which are common liabilities in drug candidates.

In synthetic chemistry, this compound can be employed in coupling reactions with acyl chlorides, isocyanates, or activated esters to construct diverse nitrogen-containing heterocycles or amide frameworks. It is also useful in asymmetric synthesis, where the chiral amine serves as a precursor or intermediate in the preparation of more complex stereodefined compounds.

Although no therapeutic drug is currently known to be based directly on (S)-Oxetan-2-ylmethanamine, its components—chiral amines and oxetane motifs—have been widely integrated into the structures of numerous drug candidates and marketed drugs due to their beneficial pharmacological and physicochemical characteristics.

This compound illustrates how combining a rigid, strained ring system with a stereocenter and a reactive amine group can create a versatile reagent for modern medicinal and synthetic chemistry.