(S)-2-Amino-2-(3-bromophenyl)ethanol: Properties & Lab Guide

(S)-2-Amino-2-(3-bromophenyl)ethanol is an enantiopure chiral amino alcohol building block widely employed in asymmetric synthesis, pharmaceutical intermediate preparation, and chiral ligand development.

Chemical Name

(S)-2-Amino-2-(3-bromophenyl)ethanol

SKU

A734554

Molecular Formula

C8H10BrNO

Molecular Weight

216.08 g/mol

Stereochemistry

S-configuration at the α-carbon (enantiopure)

Key Functional Groups

Primary amine (–NH2), primary alcohol (–OH), aryl bromide

Supplier

Aladdin Scientific

Chemical Identity and Physicochemical Properties

(S)-2-Amino-2-(3-bromophenyl)ethanol (CAS number should be verified; SKU A734554) is a chiral, bifunctional small molecule bearing a primary amine and a primary hydroxyl group on adjacent carbons, along with a meta-bromo substituent on the phenyl ring. The molecular formula is C₈H₁₀BrNO, giving a molecular weight of approximately 216.08 g/mol.

The compound exists as a single enantiomer with S-configuration at the stereogenic α-carbon, making it suitable for applications where enantiopurity is critical. The aryl bromide moiety provides a versatile handle for transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki, Negishi, Buchwald–Hartwig), while the amino alcohol scaffold confers hydrogen-bond donor/acceptor capacity relevant to both catalysis and biological interactions.

Typical physicochemical characteristics of structurally related amino alcohols include a solid or low-melting solid state at room temperature, moderate water solubility due to the polar amine and hydroxyl groups, and UV activity attributable to the brominated aromatic ring. Exact melting point, optical rotation, and solubility data should be confirmed against the current Aladdin Scientific certificate of analysis (CoA).

Synthetic Applications and Research Uses

Chiral amino alcohols of this class serve as versatile intermediates and ligands across multiple domains of synthetic chemistry:

• Pharmaceutical intermediate synthesis: The (S)-amino alcohol core is a privileged scaffold found in numerous bioactive molecules and drug candidates. The meta-bromophenyl variant enables downstream diversification via cross-coupling, facilitating lead optimization and SAR studies.
• Chiral ligand and catalyst preparation: Amino alcohols are well-established as ligands for asymmetric catalysis, including asymmetric reduction, diethylzinc addition to aldehydes, and CBS-type reductions. This compound can be elaborated into oxazoline or amino alcohol ligands.
• Chiral auxiliary applications: The stereodefined center can serve as a chiral inductor when incorporated into substrates undergoing asymmetric transformations.
• Cross-coupling diversification: The aryl bromide is reactive toward Pd-catalyzed coupling (Suzuki–Miyaura, Heck, Sonogashira) and Cu-mediated reactions, enabling rapid construction of diverse analogue libraries.

Researchers in medicinal chemistry, asymmetric synthesis, and process chemistry will find this building block particularly valuable for generating enantiopure arylglycine derivatives and related structures.

Handling, Storage, and Safety Guidelines

Although specific GHS hazard classifications for (S)-2-Amino-2-(3-bromophenyl)ethanol should be confirmed from the current Safety Data Sheet (SDS) available from Aladdin Scientific, the following general guidelines apply to compounds of this structural class:

• Personal Protective Equipment (PPE): Wear nitrile gloves, laboratory coat, and safety goggles when handling. Work in a well-ventilated area or fume hood, particularly when weighing powders to minimize inhalation exposure.
• Storage: Store in a tightly sealed container under inert atmosphere (nitrogen or argon) in a cool, dry location away from light and incompatible oxidizing agents. Refrigerated storage (2–8 °C) is typically recommended for enantiopure amino alcohol building blocks to preserve optical purity and prevent degradation over time.
• Stability: The free amine may be susceptible to oxidation and carbamation upon prolonged exposure to atmospheric CO₂; therefore, minimize air exposure during weighing and transfer operations.
• Waste disposal: Dispose of residues in accordance with local and institutional hazardous waste regulations. Consult the SDS for specific disposal guidance.

Always consult the current Aladdin Scientific SDS before use. Exact hazard statements and precautionary statements must be sourced from that document.

Quality, Purity, and Procurement Guidance

For asymmetric synthesis and pharmaceutical applications, enantiomeric excess (ee) and chemical purity are the two most critical quality parameters for (S)-2-Amino-2-(3-bromophenyl)ethanol.

• Enantiomeric excess: Aladdin Scientific provides a certificate of analysis (CoA) with each lot. Researchers should request or download the CoA to confirm the reported ee value (typically ≥98% ee for research-grade chiral building blocks, but this must be verified from the actual CoA).
• Chemical purity: HPLC or GC purity data on the CoA will indicate chemical purity. For sensitive catalytic or biological applications, additional purification (recrystallization, column chromatography) may be considered if required.
• Analytical verification: Independent verification can be performed by chiral HPLC, optical rotation measurement ([α]D), and ¹H/¹³C NMR to confirm structure and configuration.
• Ordering: Order SKU A734554 directly through Aladdin Scientific. Contact your regional Aladdin Scientific representative for bulk quantities, custom packaging, or additional technical support.

Frequently asked questions

What is the recommended storage condition for (S)-2-Amino-2-(3-bromophenyl)ethanol (A734554)?

This compound should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon) at 2–8 °C, protected from light and moisture. These conditions help preserve both chemical integrity and enantiomeric purity. Always verify specific storage requirements against the current Aladdin Scientific CoA and SDS.

How can I confirm the enantiomeric purity of (S)-2-Amino-2-(3-bromophenyl)ethanol?

Enantiomeric purity can be confirmed by chiral HPLC using an appropriate chiral stationary phase, or by measuring the specific optical rotation ([α]D) and comparing it with literature values for the S-enantiomer. The Aladdin Scientific certificate of analysis (CoA) for each lot also reports the ee value.

What cross-coupling reactions can be performed using the aryl bromide in (S)-2-Amino-2-(3-bromophenyl)ethanol?

The meta-aryl bromide is reactive in a range of palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura (with boronic acids), Heck (with alkenes), Sonogashira (with terminal alkynes), and Negishi (with organozinc reagents) couplings. Copper-mediated Ullmann-type reactions and Buchwald–Hartwig amination are also applicable. Protecting the amine and alcohol groups may be necessary depending on reaction conditions.

Is (S)-2-Amino-2-(3-bromophenyl)ethanol suitable for use as a chiral ligand precursor?

Yes. Chiral amino alcohols are well-established precursors for a variety of asymmetric catalytic ligands, including oxazolines, Schiff base ligands, and modified CBS catalysts. The primary amine and hydroxyl groups in this compound provide two points for further functionalization in ligand synthesis.

What solvents are suitable for dissolving (S)-2-Amino-2-(3-bromophenyl)ethanol?

Based on its bifunctional polar structure (amine and alcohol groups), this compound is expected to be soluble in polar protic solvents such as methanol, ethanol, and water, as well as polar aprotic solvents such as DMSO and DMF. Solubility in non-polar solvents such as hexane or diethyl ether is expected to be limited. Exact solubility data should be confirmed from the CoA or by experimental testing.

References

1. Aladdin Scientific Product Page: (S)-2-Amino-2-(3-bromophenyl)ethanol, SKU A734554. Aladdin Scientific.
2. Noyori, R.; Ohkuma, T. Asymmetric Catalysis by Architectural and Functional Molecular Engineering. Angew. Chem. Int. Ed. 2001, 40, 40–73.
3. Itsuno, S. Hydride Reduction of Carbonyl Groups. Org. React. 1998, 52, 395–576. (General reference on amino alcohol-based chiral catalysts.)
4. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.