(1-Phenylcyclopropyl)methylamine HCl: Properties & Applications
(1-Phenylcyclopropyl)methylamine HCl: Properties & Applications
(1-Phenylcyclopropyl)methylamine Hydrochloride is a strained-ring amine building block widely employed in medicinal chemistry for the synthesis of pharmacologically active compounds, offering a unique three-dimensional scaffold that enhances molecular rigidity and target selectivity.
- Product Name
- (1-Phenylcyclopropyl)methylamine Hydrochloride
- SKU
- M730119
- Core Structural Feature
- Cyclopropyl ring bearing a phenyl substituent at C-1 and a primary aminomethyl group
- Salt Form
- Hydrochloride (HCl) salt, improving stability and handling relative to the free base
- Primary Application
- Synthetic building block in medicinal chemistry, fragment-based drug discovery, and pharmaceutical synthesis
- Supplier
- Aladdin Scientific
Chemical Structure and Key Properties
(1-Phenylcyclopropyl)methylamine Hydrochloride features a cyclopropane ring substituted at the 1-position with both a phenyl group and a methylamine side chain, presented as its hydrochloride salt. The strained three-membered carbocyclic ring imparts significant conformational rigidity to any molecule into which it is incorporated, a property highly valued in drug design for restricting unwanted rotational freedom and improving binding selectivity.
The hydrochloride salt form is the preferred commercial presentation for primary amine-containing compounds of this class. Conversion to the salt enhances aqueous solubility, reduces volatility, and improves bench-top stability relative to the free base, thereby simplifying weighing and handling in the laboratory. The compound contains a primary amine functional group (–CH₂NH₂·HCl) that is reactive toward electrophiles including acid chlorides, isocyanates, aldehydes, and activated esters, making it versatile in multi-step synthesis.
Applications in Medicinal Chemistry and Drug Discovery
Cyclopropylamine-containing scaffolds occupy an important niche in medicinal chemistry. The cyclopropyl group is known as a bioisostere for vinyl groups and certain sp²-hybridized motifs, and its incorporation can modulate metabolic stability, lipophilicity, and potency of drug candidates. (1-Phenylcyclopropyl)methylamine Hydrochloride provides a quaternary carbon center adjacent to the cyclopropyl ring, which introduces steric bulk and restricts conformational flexibility — features frequently exploited in the design of protease inhibitors, kinase inhibitors, and central nervous system (CNS) drug candidates.
In fragment-based drug discovery (FBDD), small rigid amines such as this compound are valuable fragment building blocks due to their three-dimensionality and the presence of a primary amine handle that enables rapid library synthesis through amide bond formation, reductive amination, and sulfonamide coupling. The phenyl group further provides opportunities for π–π stacking interactions with aromatic residues in protein binding sites.
Researchers may also employ this compound as a chiral resolution precursor or as a starting material for the preparation of more complex cyclopropane-containing natural product analogs.
Handling, Storage, and Safety Considerations
As with all primary amine hydrochloride salts, (1-Phenylcyclopropyl)methylamine Hydrochloride should be handled in a well-ventilated fume hood using appropriate personal protective equipment (PPE), including nitrile gloves, laboratory coat, and safety glasses. The compound should be treated as a potential irritant to skin, eyes, and the respiratory tract until specific toxicological data have been established for this particular substance.
For storage, the reagent should be kept in a tightly sealed container away from moisture, heat, and incompatible materials such as strong oxidizing agents and strong acids. Storage at room temperature under dry conditions is typically appropriate for stable hydrochloride salts; however, users should consult the product-specific Certificate of Analysis (CoA) and Safety Data Sheet (SDS) supplied by Aladdin Scientific for definitive storage temperature recommendations and confirmed purity data.
When preparing solutions, note that the compound is provided as the HCl salt. If the free base form is required for a reaction, treatment with an appropriate base (e.g., triethylamine, sodium carbonate, or sodium hydroxide solution) prior to or in situ during the reaction is standard practice. Weigh quantities should be performed rapidly to minimize atmospheric moisture uptake.
Ordering and Availability from Aladdin Scientific
(1-Phenylcyclopropyl)methylamine Hydrochloride is available from Aladdin Scientific under SKU M730119. Aladdin Scientific maintains rigorous quality control processes, and each lot is accompanied by a Certificate of Analysis specifying purity, appearance, and characterization data. Researchers requiring documentation for regulatory submissions or internal quality audits may request copies of the CoA and SDS directly through the Aladdin Scientific website or customer service team.
For bulk quantities, custom packaging, or specific purity grades beyond standard catalog offerings, procurement managers and lab managers are encouraged to contact Aladdin Scientific's technical sales team to discuss requirements and obtain a tailored quotation. Aladdin Scientific ships internationally and can advise on appropriate packaging for transport in compliance with applicable regulations governing amine-containing compounds.
Frequently asked questions
What is the primary use of (1-Phenylcyclopropyl)methylamine Hydrochloride in research?
This compound is primarily used as a synthetic building block in medicinal chemistry and pharmaceutical research. Its rigid cyclopropyl scaffold, combined with a reactive primary amine group, makes it valuable for constructing drug candidates via amide coupling, reductive amination, and related transformations.
Why is the compound supplied as a hydrochloride salt rather than the free base?
The hydrochloride salt form offers superior bench stability, reduced hygroscopicity in many cases, and improved ease of handling compared to the free base amine, which can be volatile, moisture-sensitive, or difficult to weigh accurately. The salt can be conveniently converted to the free base in situ using a mild base during reaction setup.
How should I store (1-Phenylcyclopropyl)methylamine Hydrochloride to maintain its integrity?
Store the compound in a tightly sealed container under dry conditions, away from moisture, light, and heat sources. Always consult the product-specific Safety Data Sheet and Certificate of Analysis from Aladdin Scientific for confirmed storage temperature and any special handling requirements relevant to this specific lot.
Is (1-Phenylcyclopropyl)methylamine Hydrochloride available in bulk quantities?
Yes. For bulk orders or custom packaging beyond standard catalog pack sizes, please contact Aladdin Scientific's technical sales team. They can provide pricing, lead times, and ensure appropriate documentation and shipping compliance for larger quantities.
References
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for cyclopropane chemistry and amine reactivity.)
- Erlanson, D. A.; Fesik, S. W.; Hubbard, R. E.; Jahnke, W.; Jhoti, H. Twenty years on: the impact of fragments on drug discovery. Nature Reviews Drug Discovery, 2016, 15, 605–619. (Background on fragment-based drug discovery and building block utility.) doi:10.1038/nrd.2016.109
- Nicolaou, K. C.; Vourloumis, D.; Winssinger, N.; Baran, P. S. The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century. Angewandte Chemie International Edition, 2000, 39, 44–122. (General reference for use of strained ring systems in complex molecule synthesis.) doi:10.1002/(SICI)1521-3773(20000103)39:1<44::AID-ANIE44>3.0.CO;2-L
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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