(R)-2-Amino-2-(4-bromophenyl)ethanol hydrochloride
[CAS# 1916569-82-8]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Amino alcohol derivative
• Name: (R)-2-Amino-2-(4-bromophenyl)ethanol hydrochloride
• Synonyms: (2R)-2-amino-2-(4-bromophenyl)ethanol;hydrochloride
• Protein Sequence: X
• Molecular Formula: C₈H₁₁BrClNO
• Molecular Weight: 252.54
• CAS Registry Number: 1916569-82-8
• SMILES: C1=CC(=CC=C1[C@H](CO)N)Br.Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

(R)-2-Amino-2-(4-bromophenyl)ethanol hydrochloride is a chiral compound featuring an amino group and a hydroxyl group on an ethyl chain, with a 4-bromophenyl group attached to the second carbon. The compound exists as a hydrochloride salt, indicating the presence of a chloride ion associated with the amino group in the molecule. The (R) configuration refers to the specific stereochemical arrangement of the molecule, where the amino group and hydroxyl group are oriented in a particular three-dimensional space relative to the phenyl ring.

The structure of (R)-2-amino-2-(4-bromophenyl)ethanol hydrochloride includes the following key features:

1. **Chiral Center**: The (R)-configuration at the second carbon of the ethyl chain gives the compound its stereochemistry, which can have a significant effect on its biological activity. Chiral molecules can interact differently with biological systems, including enzymes, receptors, and transporters, depending on their three-dimensional shape. This can affect the potency and selectivity of a drug candidate.

2. **Amino Group**: The amino group (-NH2) at position 2 of the ethyl chain makes this molecule a potential amine for further chemical modification. Amino alcohols like this one are commonly used in the synthesis of biologically active molecules, including pharmaceuticals, and can undergo reactions such as alkylation, acylation, or peptide bond formation.

3. **Hydroxyl Group**: The hydroxyl group (-OH) at position 2 contributes to the compound's solubility in water and its ability to form hydrogen bonds with biological molecules. The hydroxyl group may also influence the molecule's pharmacokinetic properties, including its bioavailability and membrane permeability.

4. **4-Bromophenyl Group**: The 4-bromophenyl group provides an aromatic ring that is electronically modified by the presence of the bromine atom. Bromine, as a halogen, can increase the electron density of the ring and enhance its reactivity in electrophilic aromatic substitution reactions. It also makes the molecule potentially more lipophilic, which could be beneficial in optimizing the compound’s ability to cross lipid membranes and reach its target in the body.

5. **Hydrochloride Salt**: The hydrochloride salt form of (R)-2-amino-2-(4-bromophenyl)ethanol indicates that the amine group is protonated and paired with a chloride ion. The hydrochloride salt form is often used to improve the solubility and stability of organic compounds, particularly in pharmaceutical formulations.

In terms of **applications**, (R)-2-amino-2-(4-bromophenyl)ethanol hydrochloride could be valuable in drug discovery, particularly in the design of chiral molecules with specific interactions with biological targets. The amino alcohol structure is a common scaffold for molecules with diverse biological activities, including acting as neurotransmitter modulators, enzyme inhibitors, and receptor agonists or antagonists. The presence of the 4-bromophenyl group could also make it useful in the development of compounds targeting specific receptors or enzymes that are known to interact with halogenated aromatic rings.

The **synthesis** of (R)-2-amino-2-(4-bromophenyl)ethanol hydrochloride would typically involve the asymmetric synthesis of the chiral center at position 2, followed by the introduction of the 4-bromophenyl group, often via a nucleophilic substitution reaction. The compound could then be converted into its hydrochloride salt form by reacting with hydrochloric acid.

In conclusion, (R)-2-amino-2-(4-bromophenyl)ethanol hydrochloride is a chiral compound with functional groups that make it versatile for synthetic chemistry and potential applications in pharmaceuticals. Its amino alcohol structure, combined with the bromophenyl group and hydrochloride salt form, suggests that it could be a candidate for drug development, particularly in targeting specific receptors or enzymes in the body.