(S)-(+)-2-Amino-1-butanol: Properties, Uses & FAQs
(S)-(+)-2-Amino-1-butanol: Properties, Uses & FAQs
(S)-(+)-2-Amino-1-butanol is an enantiopure chiral amino alcohol widely used as a synthetic building block, chiral auxiliary, and pharmaceutical intermediate in asymmetric synthesis research.
- CAS Number
- 5856-62-2
- Molecular Formula
- C₄H₁₁NO
- Molecular Weight
- 89.14 g/mol
- Optical Activity
- (S)-(+) configuration; dextrorotatory
- Appearance
- Colorless to pale yellow liquid
- Key Application
- Chiral auxiliary and building block in asymmetric synthesis
- Aladdin SKU
- A107264
What Is (S)-(+)-2-Amino-1-butanol?
(S)-(+)-2-Amino-1-butanol is a chiral, bifunctional small molecule bearing both a primary hydroxyl group and a primary amine on adjacent carbons, with the stereocentre at C-2 adopting the S absolute configuration. Its dextrorotatory optical activity is indicated by the (+) descriptor. The compound belongs to the class of 1,2-amino alcohols (vicinal amino alcohols), which are versatile intermediates in synthetic chemistry.
The molecule's dual nucleophilic functionality — the amine and the hydroxyl — allows it to participate in a broad range of transformations, including condensation reactions, reductive aminations, and heterocycle formation. Its well-defined stereochemistry makes it particularly valuable wherever enantioselectivity must be preserved or transferred during synthesis.
Handling, Storage, and Safety
Storage: (S)-(+)-2-Amino-1-butanol should be stored in a tightly sealed container in a cool, dry, well-ventilated area, away from incompatible materials such as strong acids and oxidising agents. Refrigerated storage (2–8 °C) is typically recommended to maintain long-term stability and optical purity.
Handling precautions: The compound is an amine and may be corrosive or irritating to skin, eyes, and the respiratory tract. Work in a well-ventilated fume hood, wear appropriate personal protective equipment (nitrile gloves, safety goggles, lab coat), and avoid inhalation of vapours. Consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific before use.
Waste disposal: Dispose of residues and contaminated materials in accordance with local, regional, and national regulations governing amine-containing chemical waste.
Research and Synthetic Applications
(S)-(+)-2-Amino-1-butanol is principally exploited as a chiral building block and chiral auxiliary in asymmetric synthesis. Its 1,2-amino alcohol scaffold is a common motif in the synthesis of oxazolidinone chiral auxiliaries (e.g., Evans-type auxiliaries), which are widely used to control stereochemical outcomes in aldol, alkylation, and Diels–Alder reactions.
The compound also serves as a starting material for the preparation of chiral ligands used in asymmetric catalysis, including amino-alcohol-derived ligands for metal-catalysed enantioselective reductions and additions. In medicinal chemistry, the amino alcohol framework appears in a range of biologically active structures, and (S)-(+)-2-Amino-1-butanol can serve as a precursor in the synthesis of such targets.
Additional applications include its use as a resolving agent for racemic acids and as an intermediate in the manufacture of agrochemicals and specialty polymers.
Purity, Grade, and Quality Specifications
Aladdin Scientific supplies (S)-(+)-2-Amino-1-butanol (SKU: A107264) at a research-grade purity level. Key quality attributes for this class of enantiopure compound typically include:
- Chemical purity: Assessed by GC or HPLC to confirm absence of significant achiral or other impurities.
- Enantiomeric excess (ee): A critical specification for chiral reagents; high ee ensures reliable stereocontrol in downstream reactions. Consult the Certificate of Analysis (CoA) for the specific lot value.
- Optical rotation: Measured to confirm the (+) sign and magnitude consistent with the S configuration.
Always request and review the CoA for the specific lot number before use in enantioselective applications, as ee and purity values may vary between lots.
Ordering and Product Information
(S)-(+)-2-Amino-1-butanol is available from Aladdin Scientific under SKU A107264. To place an order or request a quotation, visit the Aladdin Scientific website and search by SKU or product name. Bulk quantities and custom packaging may be available upon request — contact our sales team for details.
For technical questions regarding purity, specifications, or application support, contact Aladdin Scientific technical support with your lot number and CoA to hand. For questions about shipping conditions, payment, or returns, please refer to the relevant sections of our Help Center or contact customer service directly.
Frequently asked questions
What is the CAS number for (S)-(+)-2-Amino-1-butanol?
The CAS registry number for (S)-(+)-2-Amino-1-butanol is 5856-62-2. This number uniquely identifies the (S)-enantiomer and can be used when searching chemical databases or placing orders to ensure you receive the correct stereoisomer.
How should (S)-(+)-2-Amino-1-butanol be stored to maintain its optical purity?
The compound should be stored tightly sealed in a cool (ideally 2–8 °C), dry, and well-ventilated location, protected from heat, light, moisture, and incompatible materials such as strong acids and oxidisers. Proper storage minimises racemisation and chemical degradation, preserving the enantiomeric excess over time. Always check the specific storage recommendation on the product label and CoA.
What are the main applications of (S)-(+)-2-Amino-1-butanol in research?
(S)-(+)-2-Amino-1-butanol is primarily used as a chiral building block and chiral auxiliary in asymmetric synthesis, notably in the preparation of Evans-type oxazolidinone auxiliaries and chiral ligands for catalysis. It also finds use as a resolving agent for racemic carboxylic acids and as a pharmaceutical intermediate in the synthesis of biologically active compounds.
How do I confirm the enantiomeric purity of the (S)-(+)-2-Amino-1-butanol I received?
Enantiomeric excess (ee) is confirmed analytically by chiral HPLC or chiral GC and by optical rotation measurement. The Certificate of Analysis (CoA) supplied with each lot from Aladdin Scientific reports these values for that specific batch. If you require independent verification, submit the sample to chiral chromatographic analysis using an appropriate chiral stationary phase column.
Is (S)-(+)-2-Amino-1-butanol the same as (R)-(-)-2-Amino-1-butanol?
No. (S)-(+)-2-Amino-1-butanol and (R)-(-)-2-Amino-1-butanol are enantiomers — non-superimposable mirror images of each other. They share the same molecular formula and connectivity but have opposite absolute configurations at C-2 and opposite optical rotations. In enantioselective reactions, they will produce products of opposite stereochemistry, so it is essential to order the correct enantiomer for your application.
What safety precautions should I take when working with (S)-(+)-2-Amino-1-butanol?
As an aliphatic amine, (S)-(+)-2-Amino-1-butanol can be irritating or corrosive to skin, eyes, and the respiratory tract. Always work in a fume hood, wear nitrile gloves, safety goggles, and a lab coat, and avoid breathing vapours or mists. Consult the current Safety Data Sheet (SDS) available from Aladdin Scientific for full hazard classification, first-aid measures, and disposal guidance before handling the compound.
References
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for amino alcohol chemistry and reactivity.)
- Evans, D. A. et al. New developments in the synthesis of chiral auxiliaries based on the oxazolidinone system. (General reference for oxazolidinone chiral auxiliaries derived from amino alcohols.)
- Aladdin Scientific. Certificate of Analysis for (S)-(+)-2-Amino-1-butanol, SKU A107264. (Lot-specific purity, ee, and optical rotation data.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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