(S)-3-Amino-3-(3-(trifluoromethyl)phenyl)propanoic acid FAQ
(S)-3-Amino-3-(3-(trifluoromethyl)phenyl)propanoic acid FAQ
(S)-3-Amino-3-(3-(trifluoromethyl)phenyl)propanoic acid is a chiral β-amino acid building block bearing a meta-trifluoromethylphenyl substituent, widely used in medicinal chemistry and peptide research for the synthesis of fluorinated, stereodefined molecular scaffolds.
- Chemical Name
- (S)-3-Amino-3-(3-(trifluoromethyl)phenyl)propanoic acid
- SKU / Catalog Number
- A709981
- Compound Class
- Chiral β-amino acid (β³-amino acid)
- Key Functional Groups
- Primary amine (–NH₂), carboxylic acid (–COOH), trifluoromethyl (–CF₃)
- Stereochemistry
- S-configuration at the β-carbon
- Storage Recommendation
- Store in a cool, dry place away from light; follow supplier certificate of analysis guidance
What Is (S)-3-Amino-3-(3-(trifluoromethyl)phenyl)propanoic Acid?
(S)-3-Amino-3-(3-(trifluoromethyl)phenyl)propanoic acid (Aladdin SKU A709981) is a non-proteinogenic, enantiomerically enriched β-amino acid. Unlike α-amino acids, the amine group is located at the β-carbon, making it a β³-amino acid. The aryl substituent carries a meta-trifluoromethyl (–CF₃) group, a fluorinated moiety widely exploited in drug design to improve metabolic stability, membrane permeability, and binding selectivity.
As a chiral building block, this compound enables the introduction of a defined stereocenter into peptide mimetics, peptidomimetic drugs, and other bioactive small molecules. The S-configuration is specified by the supplier and should be confirmed via the product certificate of analysis (CoA) before use in stereoselective synthesis.
Key Physical and Chemical Properties
This compound contains three reactive functional groups: a free primary amine, a carboxylic acid, and an electron-withdrawing trifluoromethyl group on the aromatic ring. The zwitterionic character typical of amino acids means that solubility is pH-dependent; dissolution is generally facilitated in dilute aqueous acid or base, or in polar aprotic solvents such as DMSO or DMF.
The –CF₃ group is chemically robust under most standard synthesis conditions, making this building block compatible with amide coupling, Boc/Fmoc protection strategies, and reductive amination protocols. Researchers should consult the Aladdin CoA for precise data including molecular weight, purity (typically reported by HPLC), optical rotation, and appearance, as these values are lot-specific.
Handling, Safety, and Storage
As with all fine chemical reagents, standard laboratory safety precautions apply: wear appropriate personal protective equipment (gloves, lab coat, eye protection) and handle in a well-ventilated area or fume hood. Fluorinated organic compounds may release toxic hydrogen fluoride upon combustion; consult the Safety Data Sheet (SDS) supplied with each lot before use.
For long-term storage, keep the compound sealed under inert atmosphere (nitrogen or argon) in a cool, dry location away from light and moisture to prevent hydrolysis of the amine or racemization of the stereocenter. Always refer to the lot-specific CoA and SDS provided by Aladdin Scientific for authoritative storage temperature and stability data.
Applications in Research and Drug Discovery
Chiral β-amino acids such as this compound are valuable in several research contexts. In medicinal chemistry, they serve as building blocks for peptidomimetics that are resistant to proteolytic degradation, since β-peptide bonds are not efficiently cleaved by most mammalian proteases. The trifluoromethylphenyl group adds lipophilicity and can enhance binding affinity to hydrophobic pockets in target proteins.
In asymmetric synthesis, the defined S-stereocenter can be used as a chiral handle for further elaboration. The compound is also applicable in the preparation of β-lactam antibiotics, taxol side-chain analogues, and other pharmaceutical intermediates. Researchers working on CNS drug candidates may find the meta-CF₃ phenyl motif particularly relevant given its prevalence in CNS-active compounds.
Ordering and Quality Information
(S)-3-Amino-3-(3-(trifluoromethyl)phenyl)propanoic acid is available from Aladdin Scientific under catalog number A709981. Each lot is supplied with a certificate of analysis detailing purity, appearance, and other quality parameters. Customers are encouraged to review the CoA upon receipt and contact Aladdin's technical support team for any questions regarding specifications, custom quantities, or bulk pricing.
For procurement teams, Aladdin Scientific offers streamlined ordering through its online platform. Reward points, promotional pricing, and institutional account options may be available — please consult the Aladdin website or your regional sales representative for current terms. Returns and refunds are handled according to Aladdin's standard policy; contact customer service for details specific to your order.
Frequently asked questions
What is the difference between (S)- and (R)-3-amino-3-(3-(trifluoromethyl)phenyl)propanoic acid?
The (S)- and (R)-enantiomers differ only in the spatial arrangement of substituents around the β-carbon stereocenter; they are mirror images that cannot be superimposed. In biological and pharmaceutical contexts, enantiomers can exhibit markedly different activity, selectivity, and pharmacokinetic profiles, so using the correct stereoisomer is critical. Aladdin SKU A709981 specifies the S-configuration; always confirm the optical purity via the CoA before use.
In which solvents can (S)-3-amino-3-(3-(trifluoromethyl)phenyl)propanoic acid be dissolved?
As a zwitterionic β-amino acid, this compound shows pH-dependent aqueous solubility; dissolution is typically facilitated at low pH (dilute HCl) or high pH (dilute NaOH). In organic chemistry applications, polar aprotic solvents such as DMSO and DMF are commonly used. Specific solubility data are not always provided on standard CoAs, so researchers should perform a small-scale solubility test under their intended conditions before committing to a large-scale protocol.
How should I store A709981 to preserve stereochemical integrity?
To maintain enantiomeric purity, store the compound sealed under an inert atmosphere (nitrogen or argon) in a cool, dry, and dark environment. Moisture and elevated temperatures can promote racemization or decomposition of amino acid compounds. Always consult the lot-specific CoA and SDS from Aladdin Scientific for the recommended storage temperature and shelf life, and re-check optical purity by chiral HPLC if the material has been stored for an extended period.
Is (S)-3-amino-3-(3-(trifluoromethyl)phenyl)propanoic acid suitable for Fmoc solid-phase peptide synthesis (SPPS)?
β-Amino acids of this type are generally compatible with Fmoc-SPPS strategies after appropriate N-protection (e.g., Fmoc protection of the amine) and side-chain protection if required. However, β-amino acid couplings can be slower and may require optimized coupling reagents and extended reaction times compared to standard α-amino acids. Researchers should validate coupling efficiency under their specific synthesis conditions and consult the relevant literature on β-peptide synthesis.
Can I request a custom quantity or bulk order of A709981?
Aladdin Scientific accommodates custom quantity and bulk order requests for many catalog items, including A709981. Please contact Aladdin's sales team or your regional representative to discuss availability, lead times, and pricing for quantities outside the standard catalog pack sizes. Institutional pricing and account options may also be available.
References
- Seebach, D.; Beck, A. K.; Bierbaum, D. J. The World of β- and γ-Peptides Comprised of Homologated Proteinogenic Amino Acids and Other Components. Chemistry & Biodiversity, 2004.
- Müller, K.; Faeh, C.; Diederich, F. Fluorine in Pharmaceuticals: Looking Beyond Intuition. Science, 2007.
- Aladdin Scientific. Product Certificate of Analysis, A709981, (S)-3-Amino-3-(3-(trifluoromethyl)phenyl)propanoic acid. Aladdin Scientific, Shanghai.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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